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Thursday, 22 January 2015

Dr Charlotte Wiles



Charlotte Wiles
Dr Charlotte Wiles  

Chief Executive Officer, Chemtrix BV, 
Dr. Charlotte Wiles has been actively researching within the area of micro reactor technology for ten years, starting with a PhD entitled `Micro reactors in organic chemistry`, which she obtained from The University of Hull in 2003.
In the past decade she has authored many scientific papers and review articles, recently co-authoring a book on the subject 'Micro reaction technology in organic synthesis'.
More recently, she has tailored her experience to the development and evaluation of commercially available continuous flow reactors, systems and peripheral equipment.





WITH DR ANTHONY CRASTO, Dr VIJAY KRIPALANI
EXTREME RIGHT .....DR CHARLOTTE WILES. ....AT SELECTBIO FLOW CHEMISTRY CONFERENCE IN MUMBAI, INDIA,  22 JAN 2015




Chief Executive Officer: Dr Charlotte Wiles



















Starting her research in the area of continuous flow synthesis in 2000, Charlotte obtained her PhD in 2003 entitled “Microreactors in organic synthesis”.

This was followed by 5 years of Post-Doctoral research into the rapidly developing field of continuous flow synthesis, specifically in the area of heterogeneous catalysis for small molecule synthesis.

In 2008 Charlotte joined Chemtrix BV as a Senior Chemist where she worked on the commercialisation of lab-scale micro reactor apparatus.

 In 2010 she was promoted to Chief Technology Officer within Chemtrix BV where she continues to research and develop continuous flow systems and solutions for industrial partners; with more recent developments focusing on industrial flow reactors, suited towards the development of flexible tonne-scale production plants.

Over the course of her research career, Charlotte has published more than 55 peer-reviewed articles, several book chapters and in 2011 published a book “Micro reaction technology in organic synthesis”.


EMAIL
C.Wiles@chem.hull.ac.uk
c.wiles@chemtrix.com

Links
uk.linkedin.com/pub/charlotte-wiles/1b/8a/441
http://www.chemtrix.com/
http://www.chemtrix.com/downloads
http://www.researchgate.net/profile/Charlotte_Wiles
www2.hull.ac.uk/





CPhI India, Dec2015, MUMBAI, INDIA.




With Dr Charlotte Wiles, CEO, CHEMTRIX BV , Cambridge, UK at CPhI India, Dec2015, MUMBAI, INDIA......At Pi-inc (Process Intensification Experts LLP) stall, hall 5 H47,







At Pi-inc (Process Intensification Experts LLP) stall, hall 5 H47, seen is Mr Vijay Kirpalani with Charlotte wiles —

Experience

Chemtrix BV.






CEO

Chemtrix BV.
– Present
In the 5 years since the start of Chemtrix BV the Team has developed a complete product portfolio of Flow Chemistry Equipment and Services, setting up strategic partnerships with ESK Ceramics (Germany) and DSM Fine Chemicals (Austria) and it is with this strong background that Chemtrix BV will continue to grow under the Management of Dr Charlotte Wiles.

Being part of the Company since its start in 2008, and CTO of Chemtrix BV since 2010, I will continue to use my 13 years experience in the area of Flow Chemistry to grow the Company in the new role of CEO, effective as of the 7th of August 2013.







Chief Technology Officer

Chemtrix BV
– (5 years 5 months)
As the Chief Technology Officer at Chemtrix BV I am involved in the design and evaluation of equipment developed to enable users to successfully implement continuous flow reactor technology into their synthetic processes from both a research and production perspective








Post Docotoral Research Associate

The University of Hull
– (4 years 7 months)
Continuous flow organic synthesis using glass based micro reactors
www2.hull.ac.uk/




With Dr (Ms) Charlote wiles, CEO chemtrix , at IISER-PUNE, Pune INDIA on 27 Aug 2016 for Flow Chemistry Symposium + Workshop ...






IGCW | Home
www.industrialgreenchem.com
Dr. Charlotte Wiles Chief Executive Officer,







 Image result for university of hull






PDRA

Hull University
– (5 years)
Development of continuous flow reactions in custom fabricated glass micro reactors - in conjunction with Industrial partners.

Education

John Smeaton Community High School

Click and see

White paper: Continuous Manufacturing - Producing more with less
FDA Supports the use of Continuous Manufacturing
Chemtrix' KiloFlow® featured on cover of Chemical and Engineering news (C&EN)
Hydrodynamic characterization of gas-liquid-liquid slug flow and parallel-slug flow through a ...
Symposium 'Waste not want not, profit from sustainable chemistry' at Chemspec Europe 2014
Visit Chemtrix at Chemspec Europe, booth B33
Silicon Carbide micro reactors remove compatibility issues assiciated with metallic micro reactors
CHILL and Chemtrix provide Flow Chemistry services to the chemical industry
Micro Reactor Technology Education Package
Chemtrix at Informex 2014, January 21-24, Miami (FL), USA
New U.S. Application Lab!
Chemtrix expands international network with distributor in India
Norteastern University Boston (US) Demonstrates Labtrix® S1
DSM and Chemtrix sign collaboration agreement in Continuous Flow Chemistry

 

 

ORGANISATION


Organisation







 
Organisation
Chemtrix BV is located on 2 sites. In Hull (United Kingdom) Dr Charlotte Wiles (CEO) is running the Chemtrix R&D laboratory within facilities of The University of Hull. All the other activities (Management, Engineering, Product Development, Quality Assurance, Marketing & Sales) are located at the headquarters based on the Chemelot (www.chemelot.com) site in Geleen.
Chemtrix BV, Chemical Department is located at The University of Hull

Address
Cottingham Road
Hull HU6 7RX
United Kingdom
T: +44 (0) 1482 466 459
F: +44 (0) 1482 466 410
Chemtrix BV, Chemical Department








Company Profile

HISTORY
2013
DSM and Chemtrix sign collaboration agreement in Continuous Flow Chemistry
2012
Launch of Plantrix Industrial Flow Reactor
2012
ESK Ceramics acquires minorty share in Chemtrix B.V.
2011
Launch of KiloFlow®
2010
Launch of Labtrix® Start
2009
Launch of Labtrix® and Plantrix®
2009
Launch of Chemtrix USA
July 2008
Entrance of new investors
April 2008
Chemtrix BV established in Geleen
2006
Chemtrix LTD established in Hull
2005
Start negotiations between Lionix BV and The University of Hull about co-operation
2003
Change over to high quality chips purchased from Lionix BV (www.lionixbv.nl) in Enschede (the Netherlands)
2000
Dr Paul Watts starts MRT Research at the University of Hull (www.hull.ac.uk) using in-house fabricated reactors
............



 Monograph on Microreaction Technology
Thumbnail image of graphical abstract
CRC Press, Boca Raton, 2011. 453 pp., hardcover, £ 89.00.—ISBN 978-1439824719

Micro Reaction Technology in Organic Synthesis. By Charlotte Wiles and Paul Watts.

http://onlinelibrary.wiley.com/doi/10.1002/anie.201107992/abstract 

 

 

Publications Authored By Charlotte Wiles

2012Sep
Ask the experts: the challenges and benefits of flow chemistry to optimize drug development.
Future Med Chem
Future Med Chem 2012 Sep;4(14):1779-89
Neal Anderson, Krist V Gernaey, Timothy F Jamison, Manfred Kircher, Charlotte Wiles, Nicholas E Leadbeater, Graham Sandford, Paul Richardson
Against a backdrop of a struggling economic and regulatory climate, pharmaceutical companies have recently been forced to develop new ways to provide more efficient technology to meet the demands of a competitive drug industry. This issue, coupled with an increase in patent legislation and a rising generics market, makes these themes common issues in the growth of drug development. As a consequence, the importance of process chemistry and scale-up has never been more under the spotlight.

2012Feb
Solid-supported gallium triflate: an efficient catalyst for the three-component ketonic Strecker reaction.
ChemSusChem
ChemSusChem 2012 Feb 8;5(2):332-8. Epub 2011 Dec 8.
Charlotte Wiles, Paul Watts
Chemtrix BV, Burgemeester Lemmensstraat 358, 6163JT Geleen, The Netherlands. c.wiles@chemtrix.com
In light of the growing interest in the use of rare earth metal triflates as water-tolerant Lewis acid catalysts, we embarked upon the development of a solid-supported gallium triflate (PS-Ga(OTf)(2) ) derivative as a means of increasing the cleanliness and cost effectiveness of using these increasingly expensive catalytic materials in synthetic processes. Having previously highlighted the advantages associated with coupling solid-supported catalysis and the emerging area of micro-reaction technology, we screened PS-Ga(OTf)(2) for activity towards the ketonic Strecker reaction, in which the target α-aminonitriles were obtained in higher yield and purity compared to reactions reported in literature, in which the analogous homogeneous catalyst was used.


2011Nov
Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated S(N)Ar reaction.
Beilstein J Org Chem
Beilstein J Org Chem 2011 4;7:1360-71. Epub 2011 Oct 4.
Charlotte Wiles, Paul Watts
Chemtrix BV, Burgemeester Lemmensstraat 358, 6163 JT, Geleen, The Netherlands.
Whilst microwave heating has been widely demonstrated as a synthetically useful tool for rapid reaction screening, a microwave-absorbing solvent is often required in order to achieve efficient reactant heating. In comparison, microreactors can be readily heated and pressurised in order to "super-heat" the reaction mixture, meaning that microwave-transparent solvents can also be employed. To demonstrate the advantages associated with microreaction technology a series of S(N)Ar reactions were performed under continuous flow by following previously developed microwave protocols as a starting point for the investigation.

2011Jun
Recent advances in micro reaction technology.
Chem. Commun. (Camb.)
Chem Commun (Camb) 2011 Jun 29;47(23):6512-35. Epub 2011 Mar 29.
Charlotte Wiles, Paul Watts
Chemtrix BV, Burgemeester Lemmensstraat 358, 6163 JT, Geleen, The Netherlands. c.wiles@chemtrix.com
It is the intention of this review to provide the reader with a survey of the current literature pertaining to the use of micro reactors in synthetic chemistry; recent advances are briefly discussed, with references provided to assist with further reading on this rapidly growing research topic.

2011Mar
Improved method for kinetic studies in microreactors using flow manipulation and noninvasive Raman spectrometry.
J. Am. Chem. Soc.
J Am Chem Soc 2011 Mar 22;133(10):3601-8. Epub 2011 Feb 22.
Sergey Mozharov, Alison Nordon, David Littlejohn, Charlotte Wiles, Paul Watts, Paul Dallin, John M Girkin
WestCHEM, Department of Pure and Applied Chemistry and CPACT, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
A novel method has been devised to derive kinetic information about reactions in microfluidic systems. Advantages have been demonstrated over conventional procedures for a Knoevenagel condensation reaction in terms of the time required to obtain the data (fivefold reduction) and the efficient use of reagents (tenfold reduction). The procedure is based on a step change from a low (e.

2009Dec
Continuous-flow organic synthesis: a tool for the modern medicinal chemist.
Future Med Chem
Future Med Chem 2009 Dec;1(9):1593-612
Charlotte Wiles, Paul Watts
Chemtrix BV, Burgemeester Lemmensstraat 358, 6163JT Geleen, The Netherlands. c.wiles@chemtrix.com
Medicinal chemists are under increasing pressure, not only to identify lead compounds and optimize them into clinical candidates, but also to produce materials in sufficient quantities for subsequent investigation. With this in mind, continuous-flow methodology presents an opportunity to reduce the time taken to, first, identify the compound and, second, scale the process for evaluation and, where necessary, production. It is therefore the aim of this review to provide the reader with an insight into the advantages associated with the use of continuous-flow chemistry through the use of strategically selected literature examples.

2009Jul
The development and evaluation of a continuous flow process for the lipase-mediated oxidation of alkenes.
Beilstein J Org Chem
Beilstein J Org Chem 2009 2;5:27. Epub 2009 Jun 2.
Charlotte Wiles, Marcus J Hammond, Paul Watts
Department of Chemistry, The University of Hull, Cottingham Road, Hull, HU6 7RX, UK. c.wiles@chemtrix.com
We report the use of an immobilised form of Candida antarctica lipase B, Novozym((R)) 435, in a preliminary investigation into the development of a continuous flow reactor capable of performing the chemo-enzymatic oxidation of alkenes in high yield and purity, utilising the commercially available oxidant hydrogen peroxide (100 volumes). Initial investigations focussed on the lipase-mediated oxidation of 1-methylcyclohexene, with the optimised reaction conditions subsequently employed for the epoxidation of an array of aromatic and aliphatic alkenes in 97.6 to 99.

2009Apr
A microreactor for the study of biotransformations by a cross-linked gamma-lactamase enzyme.
Biotechnol J
Biotechnol J 2009 Apr;4(4):510-6
Anne Marie Hickey, Bongkot Ngamsom, Charlotte Wiles, Gillian M Greenway, Paul Watts, Jennifer A Littlechild
University of Exeter, UK.
A (+)-gamma-lactamase was precipitated, cross-linked and the resulting solid crushed prior to immobilisation within a capillary column microreactor. The microreactor was subsequently used to study enzyme stability, activity, kinetics and substrate specificity. The thermophilic (+)-gamma-lactamase retained 100% of its initial activity at the assay temperature, 80 degrees C, for 6 h and retained 52% activity after 10 h, indicating the advantage of immobilisation.

2008Jan
An optical sensor for reactive oxygen species: encapsulation of functionalised silica nanoparticles into silicate nanoprobes to reduce fluorophore leaching.
Analyst
Analyst 2008 Jan 2;133(1):71-5. Epub 2007 Oct 2.
Victoria J Hammond, Jonathan W Aylott, Gillian M Greenway, Paul Watts, Abigail Webster, Charlotte Wiles
Department of Chemistry, The University of Hull, Cottingham Road, Hull, UK HU6 7RX.
Sol-gel nanoprobes, also known as Photonic Explorer for Bioanalysis with Biologically Localised Embedding (PEBBLE), capable of performing in-vitro intracellular monitoring of reactive oxygen species have been developed using a modified form of 5(6)-carboxyfluorescein diacetate. A sol-gel matrix was selected for the design of the probes as it is photostable, optically transparent and chemically inert, and to minimise leaching of the dye from the porous matrix it was covalently immobilised to silica nanoparticles (15 nm). Using this approach,
2007Dec
Parallel synthesis in an EOF-based micro reactor.
Chem. Commun. (Camb.)
Chem Commun (Camb) 2007 Dec(46):4928-30
Charlotte Wiles, Paul Watts
The University of Hull, Hull, UK. c.wiles@chem.hull.ac.uk
We present herein a micro reactor set-up that enables parallel syntheses to be performed under electroosmotic flow conditions.

2007Nov
Improving chemical synthesis using flow reactors.
Expert Opin Drug Discov
Expert Opin Drug Discov 2007 Nov;2(11):1487-503
Charlotte Wiles, Paul Watts
University of Hull, Department of Chemistry, Cottingham Road, Hull, HU6 7RX, UK +44 (0)1482 466410 ; P.Watts@hull.ac.uk.
Owing to the competitive nature of the pharmaceutical industry, researchers involved in lead compound generation are under continued pressure to identify and develop promising programmes of research in order to secure intellectual property. The potential of a compound for therapeutic development depends not only on structural complexity, but also on the identification of synthetic strategies that will enable the compound to be prepared on the desired scale. One approach that is of present interest to the pharmaceutical industry is the use of continuous flow reactors, with the flexible nature of the technology being particularly attractive as it bridges the changes in scale required between the initial identification of a target compound and its subsequent production.

2007Mar
The use of electroosmotic flow as a pumping mechanism for semi-preparative scale continuous flow synthesis.
Chem. Commun. (Camb.)
Chem Commun (Camb) 2007 Mar 11(9):966-8. Epub 2006 Dec 11.
Charlotte Wiles, Paul Watts, Stephen J Haswell
Department of Chemistry, Faculty of Science and the Environment, The University of Hull, Cottingham Road, Hull HU6 7RX, UK.
By employing a series of reactions we demonstrate the use of electroosmotic flow as a continuous pumping mechanism suitable for semi-preparative scale synthesis, affording an array of small organic compounds, of analytical purity, with yields ranging from 0.57-1.71 g h(-1)


2007Mar
Micro reactors: a new tool for the synthetic chemist.
Org. Biomol. Chem.
Org Biomol Chem 2007 Mar 30;5(5):727-32. Epub 2007 Jan 30.
Paul Watts, Charlotte Wiles
Department of Chemistry, The University of Hull, Cottingham Road, Hull, UK. P.Watts@hull.ac.uk
This review focuses on the use of micro reactors as tools in synthetic organic chemistry, aiming to highlight the many advantages associated with their use, in particular their ability to synthesise products in high yield, purity and, where relevant, selectivity.

2007Mar
The use of solid-supported reagents for the multi-step synthesis of analytically pure alpha,beta-unsaturated compounds in miniaturized flow reactors.
Lab Chip
Lab Chip 2007 Mar 8;7(3):322-30. Epub 2007 Jan 8.
Charlotte Wiles, Paul Watts, Stephen J Haswell
Department of Chemistry, University of Hull, Hull, HU6 7RX, UK.
Micro reaction technology offers a safe, controllable and information rich technique suitable for the long-term production of pharmaceutical agents and fine chemicals. To date however, few of the syntheses performed using this technology have addressed the problems associated with product purification. With this in mind, we report herein the incorporation of multiple supported reagents into EOF-based miniaturized flow reactors for the two-step synthesis of analytically pure compounds.

2007Feb
Recent advances in synthetic micro reaction technology.
Chem. Commun. (Camb.)
Chem Commun (Camb) 2007 Feb 12(5):443-67. Epub 2006 Oct 12.
Paul Watts, Charlotte Wiles
The University of Hull, Cottingham Road, Hull, UKHU6 7RX. P.Watts@hull.ac.uk
Although in its infancy, the field of micro reaction technology is growing rapidly, with many research groups investigating the practical advantages associated with reaction miniaturisation. With this in mind, the following Feature Article aims to provide an overview of the progress made in the past decade, paying particular attention to the field of synthetic organic chemistry.

2004Jun
Stereoselective alkylation of an Evans auxiliary derivative within a pressure-driven micro reactor.
Lab Chip
Lab Chip 2004 Jun 17;4(3):171-3. Epub 2004 Mar 17.
Charlotte Wiles, Paul Watts, Stephen J Haswell, Esteban Pombo-Villar
Department of Chemistry, The University of Hull, Cottingham Road, Hull, UK HU6 7RX.
A simple technique for the diastereoselective alkylation of a metal stabilised enolate is demonstrated within a pressure-driven micro reactor whereby enhanced diastereoselectivities were obtained compared to batch. 
2002Aug
Investigation of racemisation in peptide synthesis within a micro reactor.
Lab Chip
Lab Chip 2002 Aug 17;2(3):141-4. Epub 2002 Jun 17.
Paul Watts, Charlotte Wiles, Stephen J Haswell, Esteban Pombo-Villar
Department of Chemistry, University of Hull, Cottingham Road, Hull, UKHU6 7RX.
We demonstrate that peptides derived from alpha-amino acids may be prepared in a micro reactor. The peptides were prepared in 20 min with quantitative conversion, compared to batch reactions which require prolonged reaction times. We illustrate that by using dilute reagent concentrations and short reaction times, less racemisation is observed in micro reactions than in bulk reactions.

2002May
The regioselective preparation of 1,3-diketones within a micro reactor.
Chem. Commun. (Camb.)
Chem Commun (Camb) 2002 May(10):1034-5
Charlotte Wiles, Paul Watts, Stephen J Haswell, Esteban Pombo-Villar
Department of Chemistry, Faculty of Science and the Environment, University of Hull, Cottingham Road, Hull, UK HU6 7RX.
We demonstrate a simple method for the regioselective preparation of 1,3-diketones within a micro reactor from silyl enol ethers where the products are free from both competing O-acylation and diacylation products.

2002May
1,4-addition of enolates to alpha,beta-unsaturated ketones within a micro reactor.
Lab Chip
Lab Chip 2002 May 19;2(2):62-4. Epub 2002 Apr 19.
Charlotte Wiles, Paul Watts, Stephen J Haswell, Esteban Pombo-Villar
Department of Chemistry, Faculty of Science and the Environment, University of Hull, Cottingham Road, Hull, UKHU6 7RX.
We demonstrate the formation of a series of diketone enolates and their subsequent reaction with alpha,beta-unsaturated carbonyl compounds in order to prepare a variety of Michael adducts. In all cases, the conversions observed within a micro reactor were greater than those obtained in batch.Read More...http://www.pubfacts.com/author/Charlotte+Wileshttp://www.pubfacts.com/author/Charlotte+Wiles

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  Map of Cottingham Rd, Hull, UKCottingham Rd Hull, UK

 

Cottingham Road Baptist Church, Cottingham

 

UNIV OF HULL 

Cottingham Day 

 




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Prof. Floris Rutjes






Floris Rutjes, Professor, Radboud University Nijmegen, Netherlands

Professor in Synthetic Organic Chemistry

Director Educational Institute for Molecular Sciences

 Radboud University

Map of radboud university nijmegen

Floris Rutjes is full professor in organic synthesis at Radboud University Nijmegen. His research interests comprise the application of catalysis in the synthesis of biologically relevant molecules, and synthesis in microreactors. 

 He has received several awards including the Gold Medal of the Royal Netherlands Chemical Society (KNCV, 2002) and the AstraZeneca award for research in organic chemistry (2003). 

 He is co-founder of the companies Chiralix and FutureChemistry, and in 2008 received the award of ‘Most entrepreneurial scientist of the Netherlands 2008’.

 Currently, he is also Director of the Educational Institute for Molecular Sciences at Radboud University Nijmegen.

 His research interests comprise the application of catalysis in the synthesis of biologically relevant molecules and natural products, the development of new molecular diagnostic tools for application in life sciences, and synthesis in microreactors.






links

EMAIL  f.rutjes@science.ru.nl
https://twitter.com/florisrutjes,,@Florisrutges

 http://www.soc.science.ru.nl/
facebook   https://m2.facebook.com/floris.rutjes.7

At flow chemistry conference mumbai, india 22 jan 2015

Rutjes, Prof. F.P.J.T. (Floris)


Synthetic Organic Chemistry, professor
Chair:Synthetic Organic Chemistry
Faculty:Faculty of Science
E-Mail:f.rutjes@science.ru.nl
Telephone:024-3653202
Visiting Address:Interne adressering: 50
Heyendaalseweg 135
6525 AJ Nijmegen
Postal Address:Postbus 9010
6500 GL Nijmegen

Institute for Molecular Sciences, director of education
Visiting Address:Interne adressering: 52
Heyendaalseweg 135
6525 AJ Nijmegen

Experience









Professor in Synthetic Organic Chemistry

Radboud University Nijmegen
 – Present 







Assistant professor

University of Amsterdam
 –  (3 years 10 months)






Post-doctoral fellow

The Scripps Research Institute
 –  (1 year 9 months)

Education







University of Amsterdam

PhD, Organic Synthesis


PLACE LIVED





Nijmegen, Netherlands

Current City





Heiloo

Hometown


REALTIONSHIP


Miranda Teerhuis, married





Heyendaal castle (now serving as the Faculty Club of the university) is of old the center of Heyendaal estate, where later on most Radboud University buildings have been established.






Terras

City of Nijmegen

Whether the reason for your stay in Nijmegen is to study, to work or to perform research at the university, there is a lot more to the city of Nijmegen than just the university. In your free time there are plenty of different things you can do to enjoy yourself. Whether you prefer shopping, going to a museum or to a movie, it is all possible in this city. Here you will find a listing of shopping areas, museums and movie theatres, as well as information on the Tourist Information Office.
Apart from information on culture, we also provide you with some background information on the history of Nijmegen and some interesting links. We hope you will enjoy spending time in the city of Nijmegen.
Radboud University Nijmegen
Radboud University is located in the oldest city in the Netherlands - Nijmegen. The city dates from Roman times when its name was Noviomagus or New Market. Today, it has some 165,000 inhabitants and is a safe and friendly place with a rich social and cultural life.
Situated close to the German border, Nijmegen lies on the banks of the River Waal, a branch of the Rhine. A recent survey found that local people regard students as enriching their city and find them friendly and lively. The students themselves appreciate the green surroundings and the many opportunities that the city offers for relaxation and entertainment.


Rutjes, Prof. F.P.J.T. (Floris)

Keywords:organic synthesis, combinatorial chemistry, medicines
Expertise
Professor Floris Rutjes researches new routes for the synthesis of organic molecules with specific biological properties. His group focuses both on new molecules and on improving existing routes using biocatalysis.

Professor Rutjes also develops microreactors. These are miniature systems in which the reaction channel has a diameter of 10 to 500 micrometers. Microreactors can be used for example in the optimization of chemical reactions, as well as in the simultaneous production of large numbers of substances. This allows his research group, for example, to make certain sizes of biological active molecules. The interactions of these new molecules with components in the cell are studied within the life sciences.

The research carried out by Professor Rutjes is important in the development of new drugs. Knowledge from the group is transferred to the pharmaceuticals industry through the spin-off company Chiralix.
Publications in Metis

Scientific publications:

  • Steendam, R.R.E., Brouwer, M.C.T., Huijs, E.M.E., Kulka, M.W., Meekes, H., Enckevort, W.J.P. van, Raap, J., Rutjes, F.P.J.T. & Vlieg, E. (2014). Enantiopure isoindolinones through viedma ripening. Chemistry-a European Journal, 20(42), 13527-13530. 10.1002/chem.201404320
  • Wammes, A.E.M., Hendriks, T.G., Amatdjais-Groenen, H.I.V., Wijdeven, M.A., Hest, J.C.M. van, Delft, F.L. van, Ritschel, T. & Rutjes, F.P.J.T. (2014). Influence of azide incorporation on binding affinity by small papain inhibitors. Bioorganic & Medicinal Chemistry, 22(20), 5593-5603. 10.1016/j.bmc.2014.06.001
  • Irfan, M., Eshuis, N., Spannring, P., Tessari, M., Feiters, M.C. & Rutjes, F.P.J.T. (2014).Liquid-phase parahydrogen-induced polarization (phip) with ligand-capped platinum nanoparticles. Journal of Physical Chemistry C, 118(24), 13313-13319. 10.1021/jp504698w
  • Oers, M.C.M. van, Rutjes, F.P.J.T. & Hest, J.C.M. van (2014). Cascade reactions in nanoreactors. Curr Opin Biotechnol, 28, 10-16. 10.1016/j.copbio.2013.10.011
  • Debets, M.F., Prins, J.S., Merkx, D., Berkel, S.S. van, Delft, F.L. van, Hest, J.C.M. van & Rutjes, F.P.J.T. (2014). Synthesis of dibac analogues with excellent spaac rate constants.Organic & Biomolecular Chemistry, 12(27), 5031-5037. 10.1039/c4ob00694a
  • Eshuis, N., Hermkens, N., Weerdenburg, B.J.A. van, Feiters, M.C., Rutjes, F.P.J.T., Wijmenga, S.S. & Tessari, M. (2014). Toward nanomolar detection by nmr through sabre hyperpolarization. Journal of the American Chemical Society, 136(7), 2695-2698.
  • Pijl, F. van der, Harmel, R.K., Richelle, G.J.J., Janssen, P., Delft, F.L. van & Rutjes, F.P.J.T. (2014). Organocatalytic entry into 2,6-disubstituted aza-achmatowicz piperidinones: Application to (-)-sedacryptine and its epimer. Organic Letters, 16(7), 2038-2041.
  • Ritzen, B., Richelle, G.J.J., Brocken, L., Delft, F.L. van & Rutjes, F.P.J.T. (2014). Enzyme and gold catalysis: A new enantioselective entry into functionalized 4-hydroxy-2-pyrrolines. Synlett, 25(2), 270-274.
  • Lenstra, D.C., Rutjes, F.P.J.T. & Mecinovic, J. (2014). Triphenylphosphine-catalysed amide bond formation between carboxylic acids and amines. Chemical Communications, 50(43), 5763-5766.
  • Willemsen, J.S., Megens, R.P., Roelfes, G., Hest, J.C.M. van & Rutjes, F.P.J.T. (2014). A one-pot oxidation/enantioselective oxa-michael cascade. European Journal of Organic Chemistry, 2014(14), 2892-2898.
  • Oers, M.C.M. van, Abdelmohsen, L.K.E.A., Rutjes, F.P.J.T. & Hest, J.C.M. van (2014). Aqueous asymmetric cyclopropanation reactions in polymersome membranes. Chemical Communications, 50(31), 4040-4043.
  • Brauch, S., Wang, Z.P., Oers, M.C.M. van, Hest, J.C.M. van & Rutjes, F.P.J.T. (2014). Supramolecular chemical reactors towards the application of self-assembled polymersomes in cascade reactions. Chimica Oggi-Chemistry Today, 32(3), 73-77.
  • Kalkeren, H.A. van, Grotenhuis, C. te, Haasjes, F.S., Hommersom, C.A., Rutjes, F.P.J.T. & Delft, F.L. van (2013). Catalytic staudinger/aza-wittig sequence by in situ phosphane oxide reduction. European Journal of Organic Chemistry, 2013(31), 7059-7066.
  • Jansen, P.A.M., Diepen, J.A. van, Ritzen, B., Zeeuwen, P.L.J.M., Cacciatore, I., Cornacchia, C., Vlijmen-Willems, I.M. van, Heuvel, E. de, Botman, P.N.M., Blaauw, R.H., Hermkens, P.H.H., Rutjes, F.P.J.T. & Schalkwijk, J. (2013). Discovery of small molecule vanin inhibitors: new tools to study metabolism and disease. ACS Chemical Biology, 8(3), 530-4.
  • Rachwalski, M., Vermue, N. & Rutjes, F.P.J.T. (2013). Recent advances in enzymatic and chemical deracemisation of racemic compounds. Chemical Society Reviews, 42(24), 9268-9282.
  • Blanco-Ania, D., Aben, R.W.M., Berkom, L.W.A. van, Scheeren, H.W. & Rutjes, F.P.J.T. (2013). High-pressure-mediated extension of the privileged steroid scaffold. European Journal of Organic Chemistry, n/a-n/a.
  • Kalkeren, H.A. van, Delft, F.L. van & Rutjes, F.P.J.T. (2013). Organophosphorus Catalysis to Bypass Phosphine Oxide Waste. Chemsuschem, 6(9), 1615-1624. http://dx.doi.org/10.1002/cssc.201300368
  • Gool, J.J.F. van, Broek, S.A.M.W. van den, Ripken, R.M., Nieuwland, P.J., Koch, K. & Rutjes, F.P.J.T. (2013). Highly Controlled Gas/Liquid Processes in a Continuous Lab-Scale Device. Chemical Engineering & Technology, 36(6), 1042-1046. http://dx.doi.org/10.1002/ceat.201200553
  • Rachwalski, M., Leenders, T., Kaczmarczyk, S., Kielbasinski, P., Lesniak, S. & Rutjes, F.P.J.T. (2013). Efficient catalysts for asymmetric Mannich reactions. Organic & Biomolecular Chemistry, 11(25), 4207-4213. http://dx.doi.org/10.1039/c3ob40681d
  • Boltje, T.J., Heise, T., Rutjes, F.P.J.T. & Delft, F.L. van (2013). A Divergent Method to Prepare 5-Amino-, 5-N-Acetamido-, and 5-N-Glycolylsialosides. European Journal of Organic Chemistry, 2013(24), 5257-5261. http://dx.doi.org/10.1002/ejoc.201300664
  • Weerdenburg, B.J.A. van, Gloggler, S., Eshuis, N., Engwerda, A.H.J., Smits, J.M.M., Gelder, R. de, Appelt, S., Wymenga, S.S., Tessari, M., Feiters, M.C., Blumich, B. & Rutjes, F.P.J.T. (2013). Ligand effects of NHC-iridium catalysts for signal amplification by reversible exchange (SABRE). Chemical Communications, 49(67), 7388-7390. http://dx.doi.org/10.1039/c3cc43423k
  • Willemsen, J.S., Hest, J.C.M. van & Rutjes, F.P.J.T. (2013). Aqueous reductive amination using a dendritic metal catalyst in a dialysis bag. Beilstein Journal of Organic Chemistry, 9, 960-965. http://dx.doi.org/10.3762/bjoc.9.110
  • Oers, M.C.M. van, Rutjes, F.P.J.T. & Hest, J.C.M. van (2013). Tubular polymersomes: a crosslinker-induced shape transformation. Journal of the American Chemical Society. http://dx.doi.org/10.1021/ja408754z
  • Delville, M.M.E., Hest, J.C.M. van & Rutjes, F.P.J.T. (2013). Ethyl diazoacetate synthesis in flow. Beilstein Journal of Organic Chemistry, 9, 1813-1818. http://dx.doi.org/10.3762/bjoc.9.211
  • Delville, M.M.E., Rutjes, F.P.J.T. & Hest, J.C.M. van (2013). Inline work-up in continuous flow chemistry. Abstracts of Papers - American Chemical Society, 245.
  • Debets, M.F., Hest, J.C.M. van & Rutjes, F.P.J.T. (2013). Bioorthogonal labelling of biomolecules: new functional handles and ligation methods. Organic & Biomolecular Chemistry, 1-17. http://dx.doi.org/10.1039/c3ob41329b
  • Kalkeren, H.A. van, Delft, F.L. van & Rutjes, F.P.J.T. (2013). Catalytic Appel reactions.Pure and Applied Chemistry, 85(4), 817-828. 10.1351/pac-con-12-06-13
  • Willemsen, J.S., Hest, J.C.M. van & Rutjes, F.P.J.T. (2013). Potassium formate as a small molecule switch: controlling oxidation-reduction behaviour in a two-step sequence.Chemical Communications, 49(30), 3143-3145. http://dx.doi.org/10.1039/c3cc00126a
  • Wammes, A.E.M., Fischer, M.J.E., Mol, N.J. de, Eldijk, M.B. van, Rutjes, F.P.J.T., Hest, J.C.M. van & Delft, F.L. van (2013). Site-specific peptide and protein immobilization on surface plasmon resonance chips via strain-promoted cycloaddition. Lab on a Chip, 13(10), 1863-1867. http://dx.doi.org/10.1039/c3lc41338a
  • Brinkhuis, R.P., Graaf, F. de, Hansen, M.B., Visser, T.R., Rutjes, F.P.J.T. & Hest, J.C.M. van (2013). Dynamically functionalized polymersomes via hydrazone exchange. Polymer Chemistry, 4(5), 1345-1350. 10.1039/c2py20789c
  • Kalkeren, H.A. van, Blom, A.L., Rutjes, F.P.J.T. & Huijbregts, M.A.J. (2013). On the usefulness of life cycle assessment in early chemical methodology development: the case of organophosphorus-catalyzed Appel and Wittig reactions. Green Chemistry, 15(5), 1255-1263. http://dx.doi.org/10.1039/c3gc00053b
  • Steendam, R.R.E., Harmsen, B., Meekes, H., Enckevort, W.J.P. van, Kaptein, B., Kellogg, R.M., Raap, J., Rutjes, F. & Vlieg, E. (2013). Controlling the effect of chiral impurities on viedma ripening. Crystal Growth & Design, 13(11), 4776-4780.
  • Becker, R., Broek, S.A.M.W. van den, Nieuwland, P.J., Koch, K. & Rutjes, F.P.J.T. (2012). Optimisation and Scale-up of alpha-Bromination of Acetophenone in a Continuous Flow Microreactor. Journal of Flow Chemistry, 2(3), 1-5. http://dx.doi.org/10.1556/jfc-d-12-00007
  • Berkel, S.S. van, Lee, B. van der, Delft, F.L. van, Wagenvoord, R., Hemker, C. & Rutjes, F.P.J.T. (2012). Fluorogenic peptide-based substrates for monitoring thrombin activity.ChemMedChem, 7(4), 606-617. http://dx.doi.org/10.1002/cmdc.201100560
  • Babich, L., Hartog, A.F., Hemert, L.J. van, Rutjes, Floris & Wever, R. (2012). Synthesis of carbohydrates in a continuous flow reactor by immobilized phosphatase and aldolase.Chemsuschem, 5(12), 2348-53. 10.1002/cssc.201200468
  • Kalkeren, H.A. van, Rootselaar, S. van, Haasjes, F.S., Rutjes, F.P.J.T. & Delft, F.L. van (2012). Protective group-free synthesis of 3,4-dihydroxytetrahydrofurans from carbohydrates: Formal total synthesis of sphydrofuran. CARBOHYDRATE RESEARCH, 362, 30-37. http://dx.doi.org/10.1016/j.carres.2012.09.004
  • Becker, R., Broek, S.A.M.W. van den, Nieuwland, P.J., Koch, K. & Rutjes, F.P.J.T. (2012). Optimisation and scale-up of α-bromination of acetophenone in a continuous flow microreactor. Journal of Flow Chemistry, 11(5), 401-407. http://dx.doi.org/10.1556/JFC-D-12-00007
  • Beer, R.J.A.C. de, Nuijens, T., Wiermans, L., Quaedflieg, P.J.L.M. & Rutjes, F.P.J.T. (2012). Improving the carboxyamidomethyl ester for subtilisin a-catalysed peptide synthesis. Organic & Biomolecular Chemistry, 10(33), 6767-6775. http://dx.doi.org/10.1039/c2ob25662b
  • Broek, S.A.M.W. van den, Leliveld, J.R., Becker, R., Delville, M.M.E., Nieuwland, P.J., Koch, K. & Rutjes, F.P.J.T. (2012). Continuous flow production of thermally unstable intermediates in a microreactor with inline ir-analysis: Controlled vilsmeier-haack formylation of electron-rich arenes. Organic Process Research & Development, 16(5), 934-938. http://dx.doi.org/10.1021/op2003437
  • Girones, D., Hanckmann, M., Rutjes, F.P.J.T. & Delft, F.L. van (2012). 2 '-modified neamine analogues from thiomannosides through glycosidation-stereoinversion.European Journal of Organic Chemistry, 2012(31), 4740-4750. http://dx.doi.org/10.1002/ejoc.201200084
  • Wang, Z.P., Oers, M.C.M. van, Rutjes, F.P.J.T. & Hest, J.C.M. van (2012). Polymersome colloidosomes for enzyme catalysis in a biphasic system. Angewandte Chemie-International Edition, 51(43), 10746-10750. http://dx.doi.org/10.1002/anie.201206555
  • Georgieva, J.V., Brinkhuis, R.P., Stojanov, K., Weijers, C.A.G.M., Zuilhof, H., Rutjes, F.P.J.T., Hoekstra, D., Hest, J.C.M. van & Zuhorn, I.S. (2012). Peptide-mediated blood-brain barrier transport of polymersomes. Angewandte Chemie-International Edition, 51(33), 8339-8342. http://dx.doi.org/10.1002/anie.201202001
  • Joosten, L., Laverman, P., Boerman, O.C., Roosenburg, S., Eek, A., Rutjes, Floris & Delft, F.L. van (2012). In vitro and in vivo characterization of three 68Ga- and 111 In-labeled peptides for cholecystokinin receptor imaging. Molecular Imaging, 11(5), 401-407.
  • Beer, R.J. de, Zarzycka, B., Mariman, M., Amatdjais-Groenen, H., Mulders, M.J., Quaedflieg, P.J.L.M., Delft, F.L. van, Nabuurs, S.B. & Rutjes, F.P.J.T. (2012). Papain-specific activating esters in aqueous dipeptide synthesis. Chembiochem, 13(9), 1319-1326.
  • Beer, R.J.A.C. de, Bogels, B., Schaftenaar, G., Zarzycka, B., Quaedflieg, P.J.L.M., Delft, F.L. van, Nabuurs, S.B. & Rutjes, F.P.J.T. (2012). Enzyme-Specific Activation versus Leaving Group Ability. Chembiochem, 13(12), 1785-1790.
  • Brinkhuis, R.P., Stojanov, K., Laverman, P., Eilander, J., Zuhorn, I.S., Rutjes, F.P.J.T. & Hest, J.C.M. van (2012). Size dependent biodistribution and spect imaging of in-111-labeled polymersomes. Bioconjugate Chemistry, 23(5), 958-965. http://dx.doi.org/10.1021/bc200578s
  • Berkel, S.S. van, Bogels, B.G.M., Wijdeven, M.A., Westermann, B. & Rutjes, F.P.J.T. (2012). Recent advances in asymmetric isocyanide-based multicomponent reactions.European Journal of Organic Chemistry, 2012(19), 3543-3559. http://dx.doi.org/10.1002/ejoc.201200030
  • Beer, R.J.A.C. de, Zarzycka, B., Mariman, M., Amatdjais-Groenen, H.I.V., Mulders, M.J., Quaedflieg, P.J.L.M., Delft, F.L. van, Nabuurs, S.B. & Rutjes, F.P.J.T. (2012). Papain-specific activating esters in aqueous dipeptide synthesis. Chembiochem, 13(9), 1319-1326. http://dx.doi.org/10.1002/cbic.201200017
  • Kalkeren, H.A. van, Bruins, J.J., Rutjes, F.P.J.T. & Delft, F.L. van (2012). Organophosphorus-catalysed staudinger reduction. Advanced Synthesis & Catalysis, 354(8), 1417-1421. http://dx.doi.org/10.1002/adsc.201100967
  • Stojanov, K., Georgieva, J.V., Brinkhuis, R.P., Hest, J.C.M. van, Rutjes, F.P.J.T., Dierckx, R.A.J.O., Vries, E.F.J. de & Zuhorn, I.S. (2012). In vivo biodistribution of prion- and gm1-targeted polymersomes following intravenous administration in mice. Molecular Pharmaceutics, 9(6), 1620-1627. http://dx.doi.org//10.1021/mp200621v
  • Vervisch, K., D'Hooghe, M., Rutjes, F.P.J.T. & Kimpet, N. De (2012). Chemical and enzymatic synthesis of 2-(2-carbamoylethyl)- and 2-(2-carboxyethyl)aziridines and their conversion into delta-lactams and gamma-lactones. Organic Letters, 14(1), 106-109. http://dx.doi.org/10.1021/ol202888j
  • Broek, B. van den, Becker, R., Kossl, F., Delville, M.M.E., Nieuwland, P.J., Koch, K. & Rutjes, F.P.J.T. (2012). Prilezhaev dihydroxylation of olefins in a continuous flow process.Chemsuschem, 5(2), 289-292. http://dx.doi.org/10.1002/cssc.201100342
  • Delville, M.M.E., Gool, J.J.F. van, Wijk, I.M. van, Hest, J.C.M. van & Rutjes, F.P.J.T. (2012). Synthesis of Methoxyisopropyl (MIP)-Protected (R)-Mandelonitrile and Derivatives in a Flow Reactor. Journal of Flow Chemistry, 2(4), 124-128. http://dx.doi.org/10.1556/jfc-d-12-00008
  • Babich, L., Hemert, J.C. van, Bury, A., Hartog, A.F., Falcicchio, P., Oost, J. van der, Herk, T. van, Wever, R. & Rutjes, F.P.J.T. (2011). Synthesis of non-natural carbohydrates from glycerol and aldehydes in a one-pot four-enzyme cascade reaction. Green Chemistry, 13(10), 2895-2900. hht://dx.doi.org/10.1039/c1gc15429j
  • Jawalekar, A.M., Reubsaet, E., Rutjes, F.P.J.T. & Delft, F.L. van (2011). Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes.Chemical Communications, 47(11), 3198-3200. http://dx.doi.org/10.1039/c0cc04646a
  • Waalboer, D.C.J. & Rutjes, F.P.J.T. (2011). Synthesis and biological activity of novel platencin derivatives. ITB Journal of Science, 43 A(2), 95-112.
  • Beer, R. de, Zarzycka, B., Amatdjais-Groenen, H.I.V., Jans, S.C.B., Nuijens, T., Quaedflieg, P., Delft, F.L. van, Nabuurs, S.B. & Rutjes, F.P.J.T. (2011). Papain-catalyzed peptide bond formation: Enzyme-specific activation with guanidinophenyl esters. Chembiochem, 12(14), 2201-2207. http://dx.doi.org/10.1002/cbic.201100267
  • Kalkeren, H.A. van, Leenders, S.H.A.M., Hommersom, C.R.A., Rutjes, F.P.J.T. & Delft, F.L. van (2011). In situ phosphine oxide reduction: A catalytic appel reaction. CHEMISTRY-A EUROPEAN JOURNAL, 17(40), 11290-11295. http://dx.doi.org/10.1002/chem.201101563
  • Becker, R., Koch, K., Nieuwland, P.J. & Rutjes, F.P.J.T. (2011). Flow chemistry today: Practical approaches for optimisation and scale-up. Chimica Oggi-Chemistry Today, 29(3), 47-49.
  • Debets, M.F., Van Berkel, S.S., Dommerholt, J., Dirks, A.J., Rutjes, F.P.J.T. & van Delft, F.L. (2011). Bioconjugation with strained alkenes and alkynes. Accounts of Chemical Research, 44(9), 805-815. http://dx.doi.org/10.1021/ar200059z
  • Malik, H., Kohlen, W., Jamil, M., Rutjes, F.P.J.T. & Zwanenburg, B. (2011). Aromatic a-ring analogues of orobanchol, new germination stimulants for seeds of parasitic weeds.Organic & Biomolecular Chemistry, 9(7), 2286-2293. http://dx.doi.org/10.1039/c0ob00735h
  • Brinkhuis, R.P., Visser, T.R., Rutjes, F.P.J.T. & van Hest, J.C.M. (2011). Shedding the hydrophilic mantle of polymersomes. Polymer Chemistry, 2(3), 550-552. http://dx.doi.org/10.1039/c0py00316f
  • Brinkhuis, R.P., Rutjes, F.P.J.T. & Hest, J.C.M. van (2011). Polymeric vesicles in biomedical applications. Polymer Chemistry, 2(7), 1449-1462. http://dx.doi.org/10.1039/c1py00061f
  • Nieuwland, P.J., Segers, R., Koch, K., van Hest, J.C.M. & Rutjes, F.P.J.T. (2011). Fast scale-up using microreactors: Pyrrole synthesis from micro to production scale. Organic Process Research & Development, 15(4), 783-787. http://dx.doi.org/10.1021/op100338z
  • Delville, M.M.E., Nieuwland, P.J., Janssen, P., Koch, K., van Hest, J.C.M. & Rutjes, F.P.J.T. (2011). Continuous flow azide formation: Optimization and scale-up. Chemical Engineering Journal, 167(2-3), 556-559. http://dx.doi.org/ 10.1016/j.cej.2010.08.087
  • Broek, S. van den, Nieuwland, P.J., Koch, K., Laverman, P., Brocken, L., Boerman, O.C. & Rutjes, F.P.J.T. (2011). Fast optimisation of pet tracer synthesis using automated microreactor technology. Journal of Labelled Compounds & Radiopharmaceuticals, 54, S530-S530.
  • Dommerholt, J., Schmidt, S., Sanders-Temming, R.P., Hendriks, L.J., Rutjes, F.P.J.T., Hest, J.C.M. van, Lefeber, D.J., Friedl, P.H.A. & Delft, F.L. van (2010). Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells.Angewandte Chemie-International Edition, 49(49), 9422-5.
  • Wijdeven, M.A., Willemsen, J.S. & Rutjes, F.P.J.T. (2010). The 3-Hydroxypiperidine Skeleton: Key Element in Natural Product Synthesis. European Journal of Organic Chemistry, 2010(15), 2831-2844.
  • Wijdeven, M.A., Delft, F.L. van & Rutjes, F.P.J.T. (2010). Synthesis of functionalized 3-hydroxypiperidines. Tetrahedron, 66(30), 5623-5636.
  • Broek, S.A.M.W. van den, Rensen, P.G.W., Delft, F.L. van & Rutjes, F.P.J.T. (2010). Expedient Pathway into Optically Active 2-Oxopiperidines. European Journal of Organic Chemistry, 2010(30), 5906-5912.
  • Ritzen, B., Hoekman, S., Verdasco, E.D., Delft, F.L. van & Rutjes, F.P.J.T. (2010). Enantioselective Chemoenzymatic Synthesis of cis- and trans-2,5-Disubstituted Morpholines. Journal of Organic Chemistry, 75(10), 3461-3464.
  • Malik, H., Rutjes, F.P.J.T. & Zwanenburg, B. (2010). A new efficient synthesis of GR24 and dimethyl A-ring analogues, germinating agents for seeds of the parasitic weeds Striga and Orobanche spp. Tetrahedron, 66(35), 7198-7203.
  • Malik, H., Rutjes, F.P.J.T. & Zwanenburg, B. (2010). A New Expedient Synthesis of 3-Methyl-2(5H)-furanone, the Common Substructure in Strigolactones, and Its Proposed Biosynthesis. Synthesis-Stuttgart, 2010(19), 3271-3273.
  • Debets, M.F., Doelen, C.W.J. van der, Rutjes, F.P.J.T. & Delft, F.L. van (2010). Azide: A Unique Dipole for Metal-Free Bioorthogonal Ligations. Chembiochem, 11(9), 1168-1184.
  • Blanco Ania, D., Valderas-Cortina, C., Hermkens, P.H.H., Sliedregt, L., Scheeren, H.W. & Rutjes, F.P.J.T. (2010). Synthesis of Dihydrouracils Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold. Molecules, 15(4), 2269-2301.
  • Aslam, W.M., Tabares, L.C., Andreoni, A., Canters, G.W., Rutjes, F.P.J.T. & Delft, F.L. van (2010). 2-Deoxystreptamine conjugates by truncation-derivatization of neomycin.Pharmaceuticals, 3(3), 679-701.
  • Roosenburg, S., Laverman, P., Joosten, L., Eek, A., Oyen, W.J.G., Jong, M. de, Rutjes, F.P.J.T., Delft, F.L. van & Boerman, O.C. (2010). Stabilized (111)in-labeled sCCK8 analogues for targeting CCK2-receptor positive tumors: synthesis and evaluation.Bioconjugate Chemistry, 21(4), 663-670.
  • Waalboer, D.C.J., Leenders, S.H., Schulin-Casonato, T., Delft, F.L. van & Rutjes, F.P.J.T. (2010). Total synthesis and antibiotic activity of dehydrohomoplatencin. Chemistry & Biology, 16(37), 11233-6.
  • Wijk, X.M.R. van, Oosterhof, A., Broek, S.A.M.W. van den, Griffioen, A.W., Dam, G.B. ten, Rutjes, F.P.J.T., Delft, F.L. van & Kuppevelt, A.H.M.S.M. van (2010). A 4-deoxy analogue of N-acetyl-D-glucosamine inhibits heparan sulphate expression and growth factor binding in vitro. Experimental Cell Research, 316(15), 2504-2512.
  • Nieuwland, P.J., Koch, K., Hest, J.C.M. van & Rutjes, F.P.J.T. (2010). Flow markers in microreactors: a generally applicable chromatographic method for monitoring flow rates during reactions. Open Chemical Engineering Journal, 4, 61-67.
  • Dommerholt, J., Schmidt, S., Sanders-Temming, R.P., Hendriks, L.J.A., Rutjes, F.P.J.T., Hest, J.C.M. van, Lefeber, D.J., Friedl, P.H.A. & Delft, F.L. van (2010). Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells. Angewandte Chemie, International Edition, 49(49), 9422-9425.
  • Nieuwland, P.J., Koch, K., van Harskamp, N., Wehrens, H.R.M.J., Hest, J.C.M. van & Rutjes, F.P.J.T. (2010). Flash Chemistry Extensively Optimized: High-Temperature Swern-Moffatt Oxidation in an Automated Microreactor Platform. Chemistry-an Asian Journal, 5(4), 799-805.
  • Debets, M.F., Berkel, S.S. van, Schoffelen, S., Rutjes, F.P.J.T., Hest, J.C.M. van & Delft, F.L. van (2010). Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition. Chemical Communications, 46(1), 97-99.
  • Dirks, A.J., Berkel, S.S. van, Amatdjais-Groenen, H.I.V., Rutjes, F.P.J.T., Cornelissen, J.J.L.M. & Nolte, R.J.M. (2009). Synthesis and aggregation behavior of biohybrid amphiphiles composed of a tripeptidic head group and a polystyrene tail. Soft Matter, 5(8), 1692-1704.
  • Laverman, P., Meeuwissen, S.A., Berkel, S.S. van, Oyen, W.J.G., Delft, F.L. van, Rutjes, F.P.J.T. & Boerman, O.C. (2009). In-depth evaluation of the cycloaddition--retro-Diels--Alder reaction for in vivo targeting with [(111)In]-DTPA-RGD conjugates. Nuclear Medicine & Biology, 36(7), 749-57.
  • Koch, K., Berkel, S.S. van, Wal, M. van de, Nieuwland, P.J., Hest, J.C.M. van & Rutjes, F.P.J.T. (2009). Thrombin generation test in microfluidic systems. Journal of Applied Physics, 105(10).
  • Blanco Ania, D., Hermkens, P.H.H., Sliedregt, L., Scheeren, H.W. & Rutjes, F. (2009). Synthesis of Hydantoins and Thiohydantoins Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold. Journal of Combinatorial Chemistry, 11(4), 527-538.
  • Blanco Ania, D., Hermkens, P.H.H., Sliedregt, L., Scheeren, H.W. & Rutjes, F. (2009). Synthesis of Tetrahydro-beta-carbolines and Tetrahydroisoquinolines Fused to Pyrrolidines and Solution-Phase Parallel Acylation. Journal of Combinatorial Chemistry, 11(4), 539-546.
  • Blanco Ania, D., Hermkens, P.H.H., Sliedregt, L., Scheeren, H.W. & Rutjes, F. (2009). Solution-Phase Parallel Annulation of (Thio)hydantoins to Tetrahydroisoquinolines and Tetrahydro-beta-carbolines Containing the 2-Arylethyl Amine Scaffold. Journal of Combinatorial Chemistry, 11(4), 547-555.
  • Blanco Ania, D., Hermkens, P.H.H., Sliedregt, L., Scheeren, H.W. & Rutjes, F. (2009). Synthesis of cucurbitine derivatives: facile straightforward approach to methyl 3-amino-4-aryl-1-methylpyrrolydine-3-carboxylates. Tetrahedron, 65(27), 5393-5401.
  • Huang, W., Groothuys, S., Heredia, A., Kuijpers, B.H.M., Rutjes, F., Delft, F.L. van & Wang, L.X. (2009). Enzymatic Glycosylation of Triazole-Linked GlcNAc/Glc-Peptides: Synthesis, Stability and Anti-HIV Activity of Triazole-Linked HIV-1 gp41 Glycopeptide C34 Analogues. Chembiochem, 10(7), 1234-1242.
  • Kaiser, J., Esseveldt, B.C.J. van, Segers, M.J.A., Delft, F.L. van, Smits, J.M.M., Butterworth, S. & Rutjes, F.P.J.T. (2009). Synthesis and aromatisation of cyclic enediyne-containing amino acids. Organic & Biomolecular Chemistry, 7(4), 695-705.
  • Ritzen, B., Oers, M.C.M. van, Delft, F.L. van & Rutjes, F. (2009). Enantioselective Chemoenzymatic Synthesis of trans-Aziridines. Journal of Organic Chemistry, 74(19), 7548-7551.
  • Roosenburg, S., Laverman, P., Delft, F.L. van, Eek, A., Rutjes, F. & Boerman, O.C. (2009). Synthesis and characterization of new radiolabeled CCK8 analogues for targeting CCK2 receptor expressing tumors. Amino Acids, 37, 109-109.
  • Verkade, J.M.M., Pijl, F. van der, Willems, M., Quaedflieg, P., Delft, F.L. van & Rutjes, F. (2009). An Enantioselective Organocatalytic Approach to Both Enantiomers of Lasubine II. Journal of Organic Chemistry, 74(8), 3207-3210.
  • Waalboer, D.C.J., Kalkeren, H.A. van, Schaapman, M.C., Delft, F.L. van & Rutjes, F.P.J.T. (2009). Total Synthesis and Absolute Stereochemistry of Integric Acid. Journal of Organic Chemistry, 74(22), 8878-8881.
  • Wijdeven, M.A., Berg, R.J.F. van den, Wijtmans, R., Botman, P.N.M., Blaauw, R.H., Schoemaker, H. E., Delft, F.L. van & Rutjes, F. (2009). Complementary chemoenzymatic routes to both enantiomers of febrifugine. Organic & Biomolecular Chemistry, 7(14), 2976-2980.
  • Bart, J., Kolkman, A.J., Oosthoek-de Vries, A.J., Koch, K., Nieuwland, P.J., Janssen, J.W.G., Bentum, P.J.M. van, Ampt, K.A.M., Rutjes, F.P.J.T., Wijmenga, S.S., Gardeniers, H. & Kentgens, A.P.M. (2009). A Microfluidic High-Resolution NMR Flow Probe. Journal of the American Chemical Society, 131(14), 5014-5015.
  • Matteis, V. de, Delft, F.L. van, Tiebes, J. & Rutjes, F. (2008). RCM-mediated synthesis of fluorinated cyclic hydrazines. Synlett, 2008(3), 351-354.
  • Groothuys, S., Brock, S. van den, Kuijpers, B.H.M., IJsselstijn, M., Delft, F.L. van & Rutjes, F. (2008). Ring-closing alkyne metathesis in the synthesis of alkyne-linked glycoamino acids. Synlett, 2008(1), 111-115.
  • Hekking, K.F.W., Lefort, L., Vries, A.H.M. de, Delft, F.L. van, Schoemaker, H. E., Vries, J.G. de & Rutjes, F. (2008). Synthesis of versatile building blocks through asymmetric hydrogenation of functionalized itaconic acid mono-esters. Advanced Synthesis & Catalysis, 350(1), 85-94.
  • Hekking, K.F.W., Waalboer, D.C.J., Moelands, M.A.H., Delft, F.L. van & Rutjes, F. (2008). A ring-closing metathesis approach to cyclic alpha,beta-dehydroamino acids. Advanced Synthesis and Catalysis, 350(1), 95-106.
  • Jawalekar, A.M., Meeuwenoord, N., Cremers, J.G.O., Overkleeft, H.S., Marel, G.A. van der, Rutjes, F. & Delft, F.L. van (2008). Conjugation of nucleosides and oligonucleotides by [3+2] cycloaddition. Journal of Organic Chemistry, 73(1), 287-290.
  • Kielbasinski, P., Rachwalski, M.P., Mikolajczyk, M. & Rutjes, F. (2008). Nitrilase-catalysed hydrolysis of cyanomethyl p-tolyl sulfoxide: stereochemistry and mechanism.Tetrahedron-Asymmetry, 19(5), 562-567.
  • Kuijpers, B.H.M., Groothuys, S., Hawner, C., Dam, J. ten, Quaedflieg, P., Schoemaker, H. E., Delft, F.L. van & Rutjes, F. (2008). Cu-catalyzed formation of triazole-linked glycoamino acids and application in chemoenzymatic peptide synthesis. Organic Process Research & Development, 12(3), 503-511.
  • Laverman, P., Roosenburg-van Ameijde, S., Gotthardt, M., Park, J.S., Oyen, W.J.G., Jong, M. de, Hellmich, M.R., Rutjes, F., Delft, F.L. van & Boerman, O.C. (2008). Targeting of a CCK2 receptor splice variant with In-111-labelled cholecystokinin-8 (CCK8) and In-111-labelled minigastrin. European Journal of Nuclear Medicine and Molecular Imaging, 35(2), 386-392.
  • Berkel, S.S. van, Dirks, A.J., Meeuwissen, S.A., Pingen, D.L.L., Boerman, O.C., Laverman, P., Delft, F.L. van, Cornelissen, J.J.L.M. & Rutjes, F. (2008). Application of metal-free triazole formation in the synthesis of cyclic RGD-DTPA conjugates. Chembiochem, 9(11), 1805-1815.
  • Verkade, J.M.M., Hemert, J.C. van, Quaedflieg, P.J.L.M. & Rutjes, F.P.J.T. (2008). Organocatalysed asymmetric Mannich reactions. Chemical Society Reviews, 37(1), 29-41.
  • Waalboer, D.C.J., Schaapman, M.C., Delft, F.L. van & Rutjes, F.P.J.T. (2008). High-pressure entry into platencin. Angewandte Chemie-International Edition, 47(35), 6576-6578.
  • Wijdeven, M.A., Wijtmans, R., Berg, R.J.F. van den, Noorduin, W.L., Schoemaker, H. E., Sonke, T., Delft, F.L. van, Blaauw, R.H., Fitch, R.W., Spande, T.F., Daly, J.W. & Rutjes, F.P.J.T. (2008). N,N-Acetals as N-acyliminium ion precursors: Synthesis and absolute stereochemistry of epiquinamide. Organic Letters, 10(18), 4001-4003.
  • Koch, K., Rutjes, F.P.J.T. & Hest, J.C.M. van (2008). Bioorganic reactions. In T. Wirth (Ed.),Microreactors in Organic Synthesis and Catalysis (pp. 183-209). [S.l.]: Wiley-VCH.
  • Laverman, P., Roosenburg-van Ameijde, S., Gotthardt, M., Park, J., Oyen, W.J.G., Jong, M. de, Hellmich, M.R., Rutjes, F.P.J.T., Delft, F.L. van & Boerman, O.C. (2008). Targeting of a CCK(2) receptor splice variant with (111)In-labelled cholecystokinin-8 (CCK8) and (111)In-labelled minigastrin. European Journal of Nuclear Medicine and Molecular Imaging, 35(2), 386-92.
  • Berkel, S.S. van, Dirks, A.T., Meeuwissen, S.A., Pingen, D.L.L., Boerman, O.C., Laverman, P., Delft, F.L. van, Cornelissen, J.J. & Rutjes, F.P.J.T. (2008). Application of metal-free triazole formation in the synthesis of cyclic RGD-DTPA conjugates. Chembiochem, 9(11), 1805-15.
  • Aslam, M.W., Busscher, G.F., Weiner, D.P., Gelder, R. de, Rutjes, F. & Delft, F.L. van (2008). Fully orthogonally protected 2-deoxystreptamine from kanamycin. Journal of Organic Chemistry, 73(13), 5131-5134.
  • Koch, K., Berg, R.J.F. van den, Nieuwland, P.J., Wijtmans, R., Wubbolts, M.G., Schoemaker, H.E., Rutjes, F.P.J.T. & Hest, J.C.M. van (2008). Enzymatic synthesis of optically pure cyanohydrins in microchannels using crude cell lysate. Chemical Engineering Journal, 135, S89-S92.
  • Koch, K., Berg, R.J.F. van den, Nieuwland, P.J., Wijtmans, R., Schoemaker, H. E., Hest, J.C.M. van & Rutjes, F.P.J.T. (2008). Enzymatic enantioselective C-C-bond formation in microreactors. Biotechnology and Bioengineering, 99(4), 1028-1033.
  • Kuijpers, B.H.M., Groothuys, S., Soede, A.C., Laverman, P., Boerman, O.C., Delft, F.L. van & Rutjes, F.P.J.T. (2007). Preparation and evaluation of glycosylated arginine-glycine-aspartate (RGD) derivatives for integrin targeting. Bioconjugate Chemistry, 18(6), 1847-54.
  • Verkade, J.M.M., Hemert, J.C. van, Quaedflieg, P., Schoemaker, H.E., Schurmann, M., Delft, F.L. van & Rutjes, F. (2007). Laccase-mediated deprotection of para-methoxyphenyl (PMP)-protected amines. Advanced Synthesis & Catalysis, 349(8-9), 1332-1336.
  • Broek, S. van den, Gruijters, B.W.T., Rutjes, F., Delft, F.L. van & Blaauw, R.H. (2007). A short and scalable route to orthogonally O-protected 2-deoxystreptamine. Journal of Organic Chemistry, 72(9), 3577-3580.
  • Storcken, R.P.M., Panella, L., Delft, F.L. van, Kaptein, B., Broxterman, Q.B., Schoemaker, H.E. & Rutjes, F. (2007). A cross-metathesis route to functionalized alpha-methyl alpha-substituted amino acids. Advanced Synthesis & Catalysis, 349(1-2), 161-164.
  • Kuijpers, B.H.M., Groothuys, S., Soede, A.C., Laverman, P., Boerman, O.C., Delft, F.L. van & Rutjes, F. (2007). Preparation and evaluation of glycosylated arginine-glycine-aspartate (RGD) derivatives for integrin targeting. Bioconjugate Chemistry, 18(6), 1847-1854.
  • Kielbasinski, P., Rachwalski, M.P., Wieczorek, W.M., Kwiatkowska, M.S.A., Mikolajczyk, M., Sieron, L. & Rutjes, F. (2007). Enzyme-promoted desymmetrisation of prochiral bis(cyanomethyl)phenylphosphine oxide. Tetrahedron-Asymmetry, 18(17), 2108-2112.
  • Raijmakers, R., Zendman, A.J.W., Egberts, W.T.M. Vree, Vossenaar, E.R., Raats, J.M.H., Soede-Huijbregts, C., Rutjes, F.P.J.T., Veelen, P.A. van, Drijfhout, J.W. & Pruijn, G.J.M. (2007). Methylation of arginine residues interferes with citrullination by peptidylarginine deiminases in vitro. Journal of Molecular Biology, 367(4), 1118-1129.
  • Gruijters, B.W.T., Verkade, J.M.M., Delft, F.L. van, Sijbesma, R.P., Hermkens, P.H.H. & Rutjes, F. (2007). A novel purification method in organic synthesis using hydrogen bonding. European Journal of Organic Chemistry, 4197-4204.
  • Matteis, V. de, Dufay, O., Waalboer, D.C.J., Floris, L.V.D., Tiebes, J. & Rutjes, F. (2007). An improved ring-closing metathesis approach to fluorinated and trifluoromethylated nitrogen heterocycles. European Journal of Organic Chemistry, 2667-2675.
  • Busscher, G.F., Broek, S. van den, Rutjes, F. & Delft, F.L. van (2007). Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides. Tetrahedron, 63(15), 3183-3188.
  • Dirks, A.J., Cornelissen, J.J.L.M., Delft, F.L. van, Hest, J.C.M. van, Nolte, R.J.M., Rowan, A.E. & Rutjes, F.P.J.T. (2007). From (bio)molecules to biohybrid materals with the click chemistry approach. QSAR & Combinatorial Science, 26(11-12), 1200-1210.
  • Berkel, S.S. van, Dirks, A.J., Debets, M.F., Delft, F.L. van, Cornelissen, J.J.L.M., Nolte, R.J.M. & Rutjes, F.P.J.T. (2007). Metal-free triazole formation as a tool for bioconjugation.ChemBioChem., 8, 1504-1508.
  • Kielbasinski, P., Rachwalski, M.P., Mikolajczyk, M., Szyrej, M., Wieczorek, M.W., Wijtmans, R. & Rutjes, F. (2007). Enzyme-promoted desymmetrisation of prochiral bis(cyanomethyl) sulfoxide. Advanced Synthesis & Catalysis, 349(8-9), 1387-1392.
  • Matteis, V. de, Delft, F.L. van, Jakobi, H., Lindell, S., Tiebes, J. & Rutjes, F.P.J.T. (2006). RCM-mediated synthesis of trifluoromethyl-containing nitrogen heterocycles. Journal of Organic Chemistry, 71(20), 7527-7532.
  • Matteis, V. de, Delft, F.L. van, Tiebes, J. & Rutjes, F.P.J.T. (2006). A ring-closing metathesis pathway to fluorovinyl-containing nitrogen heterocyles. European Journal of Organic Chemistry, 1166-1176.
  • Vink, M.K.S., Wijtmans, R., Reisinger, C., Berg, R.J.F. van den, Schortinghuis, C.A., Schwab, H., Schoemaker, H.E. & Rutjes, F.P.J.T. (2006). Nitrile hydrolysis activity of Rhodococcus erythropolis NCIMB 11540 whole cells. Biotechnology Journal,, 1(5), 569-573.
  • Verkade, J.M.M., Hemert, J.C. van, Quaedflieg, P., Alsters, P.L., Delft, F.L. van & Rutjes, F.P.J.T. (2006). Mild and efficient deprotection of the amine protecting p-methoxyphenyl (PMP) group. Tetrahedron Letters, 47(46), 8109-8113.
  • Huibers, M., Manuzi, A., Rutjes, F.P.J.T. & Delft, F.L. van (2006). A sulfitylation-oxidation protocol for the preparation of sulfates. Journal of Organic Chemistry, 71(19), 7473-7476.
  • Hekking, K.F.W., Moelands, M.A.H., Delft, F.L. van & Rutjes, F.P.J.T. (2006). An in-depth study on ring-closing metathesis of carbohydrate-derived alpha-alkoxyacrylates: Efficient syntheses of DAH, KDO, and 2-deoxy-beta-KDO. Journal of Organic Chemistry, 71(17), 6444-6450.
  • Groothuys, S., Kuijpers, B.H.M., Quaedflieg, P., Roelen, H., Wiertz, R.W., Blaauw, R.H., Delft, F.L. van & Rutjes, F.P.J.T. (2006). Chemoenzymatic synthesis of triazole-linked glycopeptides. Synthesis-Stuttgart, 3146-3152.
  • Wijdeven, M.A., Botman, P.N.M., Wijtmans, R., Schoemaker, H.E., Rutjes, F.P.J.T. & Blaauw, R.H. (2005). Total synthesis of (+)-epiquinamide. Organic Letters, 7(18), 4005-4007.
  • van Lingen, H.L., Delft, F.L. van, Storcken, R.P.M., Hekking, K.F.W., Klaassen, A., Smits, J.M.M., Ruskowska, P., Frelek, J. & Rutjes, F.P.J.T. (2005). Effects of extended aryl-substituted bisoxazoline ligands in asymmetric synthesis - Efficient synthesis and application of 4,4 '-bis(1-naphthyl)-, 4,4 '-bis(2-naphthyl)- and 4,4 '-bis(9-anthryl)-2,2 '-isopropylidenebis(1,3-oxazolines). European Journal of Organic Chemistry, 4975-4987.
  • Esseveldt, B.C.J. van, Vervoort, P.W.H., Delft, F.L. van & Rutjes, F.P.J.T. (2005). Novel approach to 5-substituted proline derivatives using a silver-catalyzed cyclization as the key step. Journal of Organic Chemistry, 70(5), 1791-1795.
  • Kaiser, J., Kinderman, S.S., van Esseveldt, B.C.J., Delft, F.L. van, Schoemaker, H.E., Blaauw, R.H. & Rutjes, F.P.J.T. (2005). Synthetic applications of aliphatic unsaturated alpha-H-alpha-amino acids. Organic & Biomolecular Chemistry, 3(19), 3435-3467.
  • Busscher, G.F., Rutjes, F.P.J.T. & Delft, F.L. van (2005). 2-deoxystreptamine: Central scaffold of aminoglycoside antibiotics. Chemical Reviews, 105(3), 775-791.
  • Kielbasinski, P., Rachwalski, M.P., Mikolajczyk, M., Moelands, M.A.H., Zwanenburg, B. & Rutjes, F.P.J.T. (2005). Lipase-promoted dynamic kinetic resolution of racemic beta-hydroxyalkyl sulfones. Tetrahedron-Asymmetry, 16(12), 2157-2160.
  • Kinderman, S.S., Wekking, M.M.T., Maarseveen, J.H. van, Schoemaker, H.E., Hiemstra, H. & Rutjes, F.P.J.T. (2005). Catalytic N-sulfonyliminium ion-mediated cyclizations to a-vinyl-substituted isoquinolines and beta-carbolines and applications in metathesis. Journal of Organic Chemistry, 70(14), 5519-5527.
  • Kuster, G.J.T., Kalmoua, M., Loevezijn, A. van, Sliedregt, L.A.J.M., Steen, B.J. van, Kruse, C.G., Rutjes, F.P.J.T. & Scheeren, H.W. (2005). Synthesis of spirohydantoins and spiro-2,5-diketopiperazines via resin-bound cyclic alpha,alpha-disubstituted alpha-amino esters. J. Comb.Chem, 8(1), 85-94.
  • Dirks, A.J.T., Berkel, S.S. van, Hatzakis, N.S., Opsteen, J.A., Delft, F.L. van, Cornelissen, J.J.L.M., Rowan, A.E., Hest, J.C.M. van, Rutjes, F.P.J.T. & Nolte, R.J.M. (2005). Preparation of biohybrid amphiphiles via the copper catalysed Huisgen [3+2] dipolar cycloaddition reaction. Chemical Communications, 4172-4174.
  • Matteis, V. de, Delft, F.L. van, Gelder, R. de, Tiebes, J. & Rutjes, F.P.J.T. (2004). Fluorinated (hetero)cycles via ring-closing metathesis of fluoride- and trifluoromethyl-functionalized olefins. Tetrahedron Letters, 45(5), 959-963.
  • Blaauw, R.H., Ijzendoorn, D.R., Cremers, J.G.O., Rutjes, F.P.J.T., Broxterman, Q.B. & Schoemaker, H.E. (2004). Chemo-enzymatic synthesis of chiral fluorine-containing building blocks. Chimia, 58(3), 104-107.
  • Kinderman, S.S., Gelder, R. de, Maarseveen, M.P. van, Schoemaker, H.E., Hiemstra, H. & Rutjes, F.P.J.T. (2004). Amidopalladation of alkoxyallenes applied in the synthesis of an enantiopure 1-ethylquinolizidine frog alkaloid. Journal of the American Chemical Society, 126(13), 4100-4101.
  • Wijtmans, R., Vink, M.K.S., Schoemaker, H.E., Delft, F.L. van, Blaauw, R.H. & Rutjes, F.P.J.T. (2004). Biological relevance and synthesis of C-substituted morpholine derivatives. Synthesis-Stuttgart, 641-662.
  • Busscher, G.F., Rutjes, F.P.J.T. & Delft, F.L. van (2004). Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-allylglycine. Tetrahedron Letters, 45(18), 3629-3632.
  • Borsuk, K., Delft, F.L. van, Eggen, I.F., ten Kortenaar, P.B.W., Petersen, A. & Rutjes, F.P.J.T. (2004). Application of substituted 2-(trimethylsilyl)ethyl esters to suppress diketopiperazine formation. Tetrahedron Letters, 45(18), 3585-3588.
  • IJsselstijn, M., Aguilera, B., Marel, G.A. van der, Boom, J.H. van, Delft, F.L. van, Schoemaker, H.E., Overkleeft, H.S., Rutjes, F.P.J.T. & Overhand, M. (2004). Ring-closing alkyne metathesis mediated synthesis of cyclic beta-turn mimetics. Tetrahedron Letters, 45(22), 4379-4382.
  • Kinderman, S.S., Maarseveen, J.H. van, Schoemaker, H.E., Hiemstra, H. & Rutjes, F.P.J.T. (2004). C-C bond formation via N-phosphoryliminium ions. Synthesis-Stuttgart, 1413-1418.
  • Esseveldt, B.C.J. van, Delft, F.L. van, Smits, J.M.M., Gelder, R. de, Schoemaker, H.E. & Rutjes, F.P.J.T. (2004). Transition metal-catalyzed synthesis of novel biologically relevant tryptophan analogues. Advanced Synthesis & Catalysis, 346(7), 823-834.
  • Kuijpers, B.H.M., Groothuys, S., Keereweer, A.R., Quaedflieg, PJ, Blaauw, R.H., Delft, F.L. van & Rutjes, F.P.J.T. (2004). Expedient synthesis of triazole-linked glycosyl amino acids and peptides. Org Lett, 6(18), 3123-6.
  • Busscher, G.F., Groothuys, S., Gelder, R. de, Rutjes, F.P.J.T. & Delft, F.L. van (2004). Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor.J Org Chem, 69(13), 4477-81.
  • Botman, PN, Dommerholt, J., Gelder, R. de, Broxterman, Q.B., Schoemaker, H.E., Rutjes, F.P.J.T. & Blaauw, R.H. (2004). Diastereoselective synthesis of (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives. Org Lett, 6(26), 4941-4.
  • Botman, P.N.M., Dommerholt, J., Gelder, R. de, Broxterman, Q.B., Schoemaker, H.E., Rutjes, F.P.J.T. & Blaauw, R.H. (2004). Diastereoselective synthesis of (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives. Org Lett, 6, 1523-7060.
  • Meester, W.J.N., Maarseveen, J.H. van, Kirchsteiger, K., Hermkens, P.H.H., Schoemaker, H.E., Hiemstra, H. & Rutjes, F.P.J.T. (2004). Scope and limitations of the solution and solid phase synthesis of homoallylic amines via N-acyliminium ion reactions. arkivoc, 2, 122-151.
  • van Esseveldt, B.C.J., Delft, F.L. van, Smits, J.M.M., Gelder, R. de & Rutjes, F.P.J.T. (2003). Pd-catalysed synthesis of 5-substituted proline derivatives from acetylene-containing amino acids. Synlett, 2003(15), 2354-2358.

Further results of scientific activities:

  • Rutjes, F.P.J.T., Berkel, S.S. van, Dirks, A.J. & Cornelissen, J.J.L.M. (2006) Process for the preparation of 1,4,5-trisubstituted triazoles and 3,4,5-trisubstituted triazoles, 6011073EP.
  • Verkade, J.M.M., Quaedflieg, P.J.L.M., Alsters, P.L. & Rutjes, F.P.J.T. (2006) Process for the deprotection of protected amines, 6008788EP.
  • Wiebe, P., Trieu, H., Koch, K., Nieuwland, P.J., Hest, J.C.M. van & Rutjes, F.P.J.T. (2006)Chip holder, fluidic system and chip holder system, PCT/EP2006/010299.
  • Kuijpers, B.H.M., Groothuys, S., van Delf, t.F.L., Rutjes, F.P.J.T. & Blaauw, R.H. (2005)Preparation of triazole-linked glycoamino acids and glycopeptides.
  • Drijfhout, J.W., Rutjes, F.P.J.T., Blaauw, R.H., Pruijn, G.J.M., Venrooij, W.J.W. van & Raats, J.M.H. (2004) Peptidylarginine deiminase (PAD) inhibitors, EP 04078481.
  • Rutjes, F.P.J.T., Storcken, R.P.M., Broxterman, Q.B. & Kaptein, B. (2004) Metathesis reaction involving the unsaturated side chain of an α,α-disubstituted amino acid, WO 2004101476.



Home > Chimica Oggi-Chemistry Today > Vol. 30(2) March/April 2012
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P. 6-8 / FLOW CHEMISTRY
Flow chemistry today: practical approaches for optimisation and scale-up

RENÉ BECKER1*, KASPAR KOCH1, PIETER J. NIEUWLAND1, FLORIS P.J.T. RUTJES2*
*Corresponding authors
1. FutureChemistry Holding B.V., Toernooiveld 100, 6525 EC Nijmegen, The Netherlands
2. Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands
ABSTRACT: A general methodology is presented as a practical approach to the design of a continuous flow process and its subsequent optimisation and up scaling. Three examples of such designs are shown. The continuous flow Swern-Moffatt oxidation shows that even for ultrafast reactions, the same methodology is still feasible, resulting in an 8.5 g/h synthesis rate. Also, the continuous flow synthesis of explosive azides shows that preparative-scale safety issues at a 1 g/h synthesis rate can be more adequately dealt with. Lastly, as an example of what process automation can accomplish, we present the novel application of an automated screening of a model reaction (the Fischer esterification) with on-line gas-chromatographic analysis. Using this set-up, we found optimal reaction conditions within a working day using minimal amounts of reagents and labour, resulting in the continuous production of the target ester at a 67 mL/h rate.

http://teknoscienze.com/articles/chimica-oggi-chemistry-today-flow-chemistry-today-practical-approaches-for-optimisation-and.aspx#.VMD1GEeUc9s



Recent publications:

S. Brauch, Z.P. Wang, M.C.M. van Oers, J.C.M. van Hest, F.P.J.T. Rutjes, "Supramolecular chemical reactors Towards the application of self-assembled polymersomes in cascade reactions", Chim. Oggi. 2014, 32, 73-77.
M.F. Debets, J.S. Prins, D. Merkx, S.S. van Berkel, F.L. van Delft, J.C.M. van Hest, F.P.J.T. Rutjes, "Synthesis of DIBAC analogues with excellent SPAAC rate constants", Org. Biomol. Chem. 2014, 12, 5031-5037. direct link
D.C. Lenstra, F.P.J.T. Rutjes, J. Mecinovic, "Triphenylphosphine-catalysed amide bond formation between carboxylic acids and amines",Chem. Commun. 2014, 50, 5763-5766. direct link
J.S. Willemsen, R.P. Megens, G. Roelfes, J.C.M. van Hest, F.P.J.T. Rutjes, "A One-Pot Oxidation/Enantioselective Oxa-Michael Cascade",Eur. J. Org. Chem. 2014, 2892-2898. direct link
M.C.M. van Oers, L.K.E.A. Abdelmohsen, F.P.J.T. Rutjes, J.C.M. van Hest, "Aqueous asymmetric cyclopropanation reactions in polymersome membranes", Chem. Commun. 2014, 50, 4040-4043. direct link
F. van der Pijl, R.K. Harmel, G.J.J. Richelle, P. Janssen, F.L. van Delft, F.P.J.T. Rutjes, "Organocatalytic Entry into 2,6-Disubstituted Aza-Achmatowicz Piperidinones: Application to (-)-Sedacryptine and Its Epimer", Org. Lett. 2014, 16, 2038-2041. direct link
D. Blanco-Ania, R.W.M. Aben, L.W.A. van Berkom, H.W. Scheeren, F.P.J.T. Rutjes, "High-Pressure-Mediated Extension of the Privileged Steroid Scaffold", Eur. J. Org. Chem. 2014, 1438-1444. direct link
N. Eshuis, N. Hermkens, B.J.A. van Weerdenburg, M.C. Feiters, F.P.J.T. Rutjes, S.S. Wijmenga, M. Tessari, "Toward Nanomolar Detection by NMR Through SABRE Hyperpolarization", J. Am. Chem. Soc. 2014, 136, 2695-2698. direct link
B. Ritzen, G.J.J. Richelle, L. Brocken, F.L. van Delft, F.P.J.T. Rutjes, "Enzyme and Gold Catalysis: A New Enantioselective Entry into Functionalized 4-Hydroxy-2-pyrrolines", Synlett 2014, 25, 270-274. direct link
M. Rachwalski, N. Vermue, F.P.J.T. Rutjes, "Recent advances in enzymatic and chemical deracemisation of racemic compounds", Chem. Soc. Rev. 2013, 42, 9268-9282. direct link


2013

R.P. Brinkhuis, F. de Graaf, M.B. Hansen, T.R. Visser, F.P.J.T. Rutjes, J.C.M. van Hest, "Dynamically functionalized polymersomes via hydrazone exchange", Polym. Chem. 2013, 4, 1345-1350. direct link
H.A. van Kalkeren, F.L. van Delft, F.P.J.T. Rutjes, "Catalytic Appel reactions", Pure Appl. Chem. 2013, 85, 817-828. direct link
H.A. van Kalkeren, A.L. Blom, F.P.J.T. Rutjes, M.A.J. Huijbregts, "On the usefulness of life cycle assessment in early chemical methodology development: the case of organophosphorus-catalyzed Appel and Wittig reactions", Green Chem. 2013, 15, 1255-1263.direct link
A.M. Jawalekar, S. Malik, J.M.M. Verkade, B. Gibson, N. Barta, J.C. Hodges, A. Rowan, F.L. van Delft, "Oligonucleotide tagging for copper-free click conjugation", Molecules 2013, 18, 7346-7363. direct link
P.A.M. Jansen, J.A. van Diepen, B. Ritzen, P.L.J.M. Zeeuwen, I. Cacciatore, C. Cornacchia, I.M.J.J. Vlijmen-Willems, E. de Heuvel, P.N.M. Botman, R.H. Blaauw, P.H.H. Hermkens, F.P.J.T. Rutjes, J. Schalkwijk, "Discovery of Small Molecule Vanin Inhibitors: New Tools To Study Metabolism and Disease", ACS Chem. Biol. 2013, 8, 530-534. direct link
J.S. Willemsen, J.C.M. van Hest, F.P.J.T. Rutjes, "Potassium formate as a small molecule switch: controlling oxidation-reduction behaviour in a two-step sequence", Chem. Commun. 2013, 49, 3143-3145. direct link
R.P. Temming, L. Eggermont, M.B. van Eldijk, J.C.M. van Hest, F.L. van Delft, "N-Terminal Dual Protein Functionalization by Strain-Promoted Alkyne-Nitrone Cycloaddition", Org. Biomol. Chem. 2013, 11, 2772-2779. direct link
J.S. Willemsen, J.C.M. van Hest, F.P.J.T. Rutjes, "Aqueous reductive amination using a dendritic metal catalyst in a dialysis bag",Beilstein J. Org. Chem. 2013, 9, 960-965. direct link
A.E.M. Wammes, M.J.E. Fischer, N.J. de Mol, M.B. van Eldijk, F.P.J.T. Rutjes, J.C.M. van Hest, F.L. van Delft, "Site-specific peptide and protein immobilization on surface plasmon resonance chips via strain-promoted cycloaddition", Lab Chip 2013, 13, 1863-1867. direct link
J.J.F. van Gool, S.A.M.W. van den Broek, R.M. Ripken, P.J. Nieuwland, K. Koch, F.P.J.T. Rutjes, "Highly Controlled Gas/Liquid Processes in a Continuous Lab-Scale Device", Chem. Eng. Technol. 2013, 36, 1042-1046. direct link
J. Garcia-Hartjes, J. Dommerholt, T. Wennekes, F.L. van Delft, H. Zuilhof, "Electronic Effects versus Distortion Energies During Strain-Promoted Alkyne-Azide Cycloadditions: A Theoretical Tool to Predict Reaction Kinetics", Eur. J. Org. Chem. 2013, 3712-3720. direct link
M. Rachwalski, T. Leenders, S. Kaczmarczyk, P. Kielbasinski, S. Lesniak, F.P.J.T. Rutjes, "Efficient catalysts for asymmetric Mannich reactions", Org. Biomol. Chem. 2013, 11, 4207-4213. direct link
B.J.A. van Weerdenburg, S. Gloggler, N. Eshuis, A.H.J. Engwerda, J.M.M. Smits, R. de Gelder, S. Appelt, S.S. Wymenga, M. Tessari, M.C. Feiters, B. Blumich, F.P.J.T. Rutjes, "Ligand effects of NHC-iridium catalysts for signal amplification by reversible exchange (SABRE)",Chem. Commun. 2013, 49, 7388-7390. direct link
T.J. Boltje, T. Heise, F.P.T.J. Rutjes, F.L. van Delft , "A Divergent Method to Prepare 5-Amino-, 5-N-Acetamido-, and 5-N-Glycolylsialosides", Eur. J. Org. Chem. 2013, 5257-5261. direct link
H.A. van Kalkeren, F.L. van Delft, F.P.T.J. Rutjes, "Organophosphorus Catalysis to Bypass Phosphine Oxide Waste", ChemSusChem2013, 6, 1615-1624. direct link
M.M.E. Delville, J.C.M. van Hest, F.P.J.T. Rutjes, "Ethyl diazoacetate synthesis in flow", Beilstein J. Org. Chem. 2013, 9, 1813-1818.direct link
P.A.M. Jansen, P.H.H. Hermkens, P.L.J.M. Zeeuwen, P.N.M. Botman, R.H. Blaauw, P. Burghout, P.M. van Galen, J.W. Mouton, F.P.J.T. Rutjes, J. Schalkwijk, "Combination of Pantothenamides with Vanin Inhibitors as a Novel Antibiotic Strategy against Gram-Positive Bacteria", Antimicrob. Agents Chemother. 2013, 57, 4794-4800. direct link
M.F. Debets, J.C.M. van Hest, F.P.J.T. Rutjes, "Bioorthogonal labelling of biomolecules: new functional handles and ligation methods",Org. Biomol. Chem. 2013, 11, 6439-6455. direct link
R.R.E. Steendam, B. Harmsen, H. Meekes, W.J.P. van Enckevort, B. Kaptein, R.M. Kellogg, J. Raap, F.P.J.T. Rutjes, E. Vlieg, "Controlling the Effect of Chiral Impurities on Viedma Ripening", Cryst. Growth Des. 2013, 13, 4776-4780. direct link
H.A. van Kalkeren, C. te Grotenhuis, F.S. Haasjes, C.A. Hommersom, F.P.J.T. Rutjes, F.L. van Delft, "Catalytic Staudinger/Aza-Wittig Sequence by in situ Phosphane Oxide Reduction", Eur. J. Org. Chem. 2013, 7059-7066. direct link
M.C.M. van Oers, F.P.J.T. Rutjes, J.C.M. van Hest, "Tubular Polymersomes: A Cross-Linker-Induced Shape Transformation", J. Am. Chem. Soc. 2013, 135, 16308-16311. direct link

M. Rachwalski, N. Vermue, F.P.J.T. Rutjes, "Recent advances in enzymatic and chemical deracemisation of racemic compounds", Chem. Soc. Rev. 2013, 42, 9268-9282. direct link

see............
http://www.soc.science.ru.nl/
Synthetic Organic Chemistry
Institute for Molecules and Materials
Radboud University Nijmegen
Heyendaalseweg 135
6525 AJ Nijmegen
The Netherlands

You can contact Prof. Rutjes by email at: F.Rutjes@science.ru.nl
Or by telephone or fax:
Telephone: +31 (0)24 365 3202
Fax: +31 (0)24 365 3393


Secondary functions

  • Member program committee Fine Chemicals and Pharmaceuticals Cluster CatchBio
(2008 - Heden)
  • Organic Chemistry training to various companies (occasionally)
(2003 - Heden)
  • Member program committee STW Perspective Genbiotics
(2010 - Heden)
  • Co-founder, shareholder and scientific advisor of Chiralix
(2002 - Heden)
  • Co-founder, shareholder and scientific advisor of FutureChemistry
(2007 - Heden)
  • Scientific advisor Khondrion
(2010 - Heden)
  • Member scientific advisory board Leiden‐Amsterdam Centre for Drug Research (LACDR)
(2009 - Heden)
  • Member Topteam Chemistry and Chairman steering group Innovation Labs
(2010 - Heden)
  • Co-founder, shareholder and scientific advisor of Pansynt
(2012 - Heden)
  • Member scientific advisory board J.H. van ‘t Hoff Institute for Molecular Sciences (HIMS/UvA)
(2013 - Heden)
  • Member Board TKI-NCI
(2014 - Heden)

Lecturer of the following courses:








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