One Organic Chemist One Day: Dr John Tsanaktsidis

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Sunday 4 January 2015

Dr John Tsanaktsidis

Dr John Tsanaktsidis, CSIRO Materials Science and Engineering.

Dr Tsanaktsidis is a Chief Research Consultant at CSIRO (Manufacturing Flagship) with experience in developing and delivering scientific outcomes to industry, with demonstrated achievements in scientific research and management, technology commercialisation, and business leadership.

Specialties: Flow Chemistry, Process Development, RAFT Agent Manufacture, Polymer-Drug conjugates, Fine Chemicals from Biomass, Cubane Chemistry, Technology Commercialization; Business Leadership

He was recognized in 2006 through a Distinguished Alumni Award from The Flinders University of South Australia, and in 2012 through a Chief’s Innovation Award from CMSE.

Qualifications:

BSc (Hons)
PhD

Expertise:

Synthetic organic chemistry

Current project:

Developing new chemical processes through continuous flow processing

Australian Innovation Showcase India 2013 Dr John Tsanaktsidis, CSIRO

Current activities

Dr Tsanaktsidis is a synthetic organic chemist currently focussed on:

continuous flow processing methods to chemical synthesis and its application to process development for industrial applications
RAFT polymerisation technology to drug delivery and bioactive molecule discovery
the conversion of renewable biomass feedstocks into fine chemicals and fuels.

Dr Tsanaktsidis believes that Flow Chemistry will be a revolution in fine chemical processing.

Dr Tsanaktsidis led the establishment of the Flow Chemistry Laboratory at CSIRO. This Laboratory houses a world-class capability in continuous flow processing, and represents a significant and growing capital investment by CSIRO.

This laboratory is unique in Australia and world competitive complementing CSIRO’s strengths in batch mode chemical synthesis at laboratory and pilot scale.

This new capability represents a fresh paradigm in chemical manufacturing and is being deployed in a number of commercially oriented projects, including polymer synthesis, pharmaceutical production, and conversion of renewable feed stocks into platform fine chemicals and biofuels.

Dr Tsanaktsidis believes that Flow Chemistry will be a revolution in fine chemical processing and will change the way that industrial chemicals and pharmaceuticals are manufactured in the future.

He is keen to ensure that CSIRO’s knowhow is being used to develop innovative and more competitive processes to support a new era of innovative chemical manufacturing in Australia.

Background

Dr Tsanaktsidis has undertaken an array of roles ranging from independent scientific research at the School of Chemistry, The University of Melbourne, to client funded R&D projects, business development and commercialisation, and senior management at CSIRO.

From 2005 to 2007 Dr Tsanaktsidis served as Managing Director of Boron Molecular Pty. Ltd.

He has worked with a number of multinational companies and small to medium sized enterprises on the development and commercialisation of various technologies.

Education and training

Dr Tsanaktsidis completed his Bachelor of Science (Chemistry – Honours First Class) and Doctor of Philosophy (Chemsitry) at Flinders University in South Australia.

He undertook postdoctoral studies first at the University of Chicago, USA as a Postdoctoral Research Associate in the Department of Chemistry; then as a Postdoctoral Research Fellow at the Research School of Chemistry at the Australian National University (ANU).

Further studies included:

Gustav Kaser Training – Management One
Company Directors Course Diploma, Australian Institute of Company Directors
Graduate Certificate in Management (Technology Management), APESMA-Deakin University.

FLINDERS UNIV

Awards and affiliations

Dr Tsanaktsidis has been recognised by CSIRO Project Management and Business Excellence; and in 2006 his career achievements were recognized by Flinders University of South Australia through a Distinguished Alumni Award:

John Tsanaktsidis is Managing Director of Boron Molecular Pty Ltd and it is the exception rather than the rule that chemists rise to become Chief Executives of companies. He is one of the world’s foremost experts on the chemistry of cubanes, and his Award acknowledges that, as well as, his development of a new method for preparing methoxyflurane used for delivering analgesics to trauma victims, and business leadership.

Dr Tsanaktsidis has achieved the following awards and affiliations:

Graduate, Australian Institute of Company Directors (GAICD), 2007
Distinguished Alumni Award, Flinders University, 2006
CSIRO Award for Project Management, 2004
CSIRO Award for Business Excellence, 2003
Fellow of the Royal Australian Chemical Institute (FRACI), 2000
Flinders University Overseas Travelling Award, 1986.

Publishing History

Hutt OE, Freemont JA, Littler S, Duggan PJ, Tsanaktsidis J, Ryan, JH. 2012. Staudinger and Ruzicka’s Altered Pyrethrolone: The Cyclopentadienone Dimers Derived from Pyrethrin I. Horta Acta. Accepted.

Churches QI, Mulder RJ, White LM, Tsanaktsidis J, Duggan PJ. 2012. The Synthesis of a Cubane-Substituted Dipeptide. Australian Journal of Chemistry. 65: 690–693.

Ko EJ, Williams CM, Savage GP, Tsanaktsidis J. 2012. Reductive Radical Decarboxylation of Aliphatic Carboxylic Acids. Organic Syntheses. 89: 471-479.

Moad G, Bicciocchi E, Chen M, Chiefari J, Guerrero-Sanchez C, Haeussler M, Houshyar S, Keddie D, Rizzardo E, Thang S, Tsanaktsidis J. 2012. Some Recent Developments in RAFT Polymerization. Progress in Controlled Radical Polymerization: Mechanisms and Techniques. ACS Symposium Series 2012. Chapter 16, pp 243–258.

Houshyar S, Keddie D, Moad G, Mulder R, Saubern S, Tsanaktsidis J. 2012. The Scope for Synthesis of Macro-RAFT Agents by Sequential Insertion of Single Monomer Units. Polymer Chemistry. 3: 1879-1889.

Williams CW, Thang SH, Hantke T, Vogel U, Seeberger PH, Tsanaktsidis J, Lepenies B. 2012. RAFT-derived polymer-drug conjugates: poly(hydroxypropyl methacrylamide)-SN-38 conjugates. ChemMedChem. 7: 281 – 291.

Brasholz M, Von Kaenel K, Hornung CH, Saubern S, Tsanaktsidis J. 2011. Highly efficient dehydration of carbohydrates to 5-(chloromethyl)furfural (CMF), 5-(hydroxymethyl)furfural (HMF) and levulinic acid by biphasic continuous flow processing. Green Chemistry. 13: 1114-1117.

Ko EJ, Savage GP, Williams CW, Tsanaktsidis J. 2011. Reducing the cost, smell and toxicity of the Barton reductive decarboxylation: Chloroform as the hydrogen atom source. Organic Letters. 13 (8): 1944–1947.

Griffiths RG, Tsanaktsidis J, Savage GP, Priefer R. 2010. Thermochemical properties of iodinated cubane derivatives. Thermochimica Acta. 499 (1-2): 15-20.

Brasholz M, Johnson BA, Macdonald JM, Polyzos A, Tsanaktsidis J, Saubern S, Holmes AB, Ryan JH. 2010. Flow Synthesis of Tricyclic Spiropiperidines as Building Blocks for the Histrionicotoxin Family of Alkaloids. Tetrahedron. 66: 6445.

Tsanaktsidis J, Tiekink ERT. 2001. Crystal Structure of 1-Amino-2-thionebenzothiazole, C7H6N2S2. Zeitschrift für Kristallographie - New Crystal Structures. 216: 443.

Lock JS, May BL, Clements P, Tsanaktsidis J, Easton CJ, Lincoln SF. 2001. Size Discrimination in Intramolecular Complexation of Modified Cyclodextrins: A Preparative and Nuclear Magnetic Resonance Study. Journal of Chemical Society Perkin Transactions 1. 3361.

Maxwell BJ, Smith BJ, Tsanaktsidis J. 2000. The Cyclization of N-Butyl-4-pentenylaminyl Revisited: A combined Theoretical and Experimental Study. Journal of Chemical Society Perkin Transactions 2. 425.

May BL, Clements P, Tsanaktsidis J, Easton CJ, Lincoln SF. 2000. Square Pegs in Round Holes. Preparation and Intramolecular Complexation of Cubyl Substituted a-Cyclodextrins and of an Adamantane Analogue. Journal of Chemical Society Perkin Transactions 1. 463.

Field MJ, May BL, Clements P, Tsanaktsidis J, Easton CJ, Lincoln SF. 2000. Intramolecular Complexation in Modified b-Cyclodextrins: A Preparative, Nuclear Magnetic Resonance and pH Titration Study. Journal of Chemical Society Perkin Transactions 1. 1251.

Cundy D, Gurr PA, Knill AM, Tsanaktsidis J. 2000. An improved synthesis of (S)-1-[[4-(dimethylamino)-3-methylphenyl]methyl]-5-(diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid ditrifluoroacetate dihydrate (PD123319). Arkivoc. 1: 158-164.

Maxwell BJ, Tsanaktsidis J. 1998. Book Chapter: Homolytic Addition Reactions of Dialkylaminyl Radicals. N-Centered Radicals, Z. B. Alfassi, Ed., pp 663-683, John Wiley & Sons, London.

Gable RW, Lowe DA, Tsanaktsidis J. 1998. endo-2,4-Dibromodicyclopentadiene-1,8-dione 8-Ethylene Ketal. Acta Crystallographica Section C. 151.

Bliese M, Fanning LA, Gable RW, Lowe DA, Tsanaktsidis J. 1998. Indirect Monobromination of the Cubane Nucleus. The Synthesis of Dimethyl 2-Bromocubane-1,4-dicarboxylate. Australian Journal of Chemistry. 51: 593.

Tsanaktsidis J. 1997. Book Chapter: Polysubstituted Cubanes: Towards Complete Systematic Substsitution of the Cubane Nucleus. Advances in Strain in Organic Chemistry, B. Halton, Ed. JAI Press Ltd., London, Volume 6, pp 67.

Bliese M, Tsanaktsidis J. 1997. Dimethyl 1,4-Cubanedicarboxylate: A Practical Laboratory Scale Synthesis. Australian Journal of Chemistry. 50: 189.

Smith B, Tsanaktsidis J. 1997. Cubyl Carbinyl Cation: Fact or Fiction? Journal of Organic Chemistry. 62: 5709.

Bliese M, Cristiano D, Tsanaktsidis J. 1997. Preparation of Dimethyl 2,3-Dimethyl-1,4-cubanedicarboxylate. Australian Journal of Chemistry. 50: 1043.

Bagnell L, Bliese M, Cablewski T, Strauss CS, Tsanaktsidis J. 1997. Organic Synthesis using High Temperature Aqueous Media: Preparation of 3-Methyl-2-cyclopentenone. Australian Journal of Chemistry. 50: 921.

Gable RW, Lowe DA, Tsanaktsidis J. 1997. endo-1,4,4-Tribromo-3-methyltricyclo[5.2.1.02,6]dec-8-ene-5,10-dione 10-Ethylene Ketal. Acta Crystallographica Section C. 1916.

Maxwell BJ, Tsanaktsidis J. 1996. Cyclization of N-Butyl-4-pentenylaminyl: Implications for the Cyclization of Alkenylaminyl Radicals. Journal of the American Chemical Society. 118: 4276.

Cristiano D, Gable RW, Lowe DA, Tsanaktsidis J. 1995. Dimethyl 2-Methylcubane-1,4-Dicarboxylate and Dimethyl 2,3-Dimethylcubane-1,4-dicarboxylate. Acta Crystallographica Section C. 1658.

Eaton PE, Nordari N, Tsanaktsidis J, Upadhyaya SP. 1995. Barton Decarboxylation of Cubane-1,4-diacid: Optimised Procedures for Cubanecarboxylic Acid and Cubane. Synthesis. 501.

Maxwell BJ, Tsanaktsidis J. 1994. Influence of Bis(tributyltin) Oxide on Aminyl Radical Cyclizations. Journal of the Chemical Society, Chemical Communications.533.

Gable RW, Parker KJ, Tsanaktsidis J. 1994. Selective Bromochlorination of endo-1,4-Dibromotricyclo[5.2.1.02,6]deca-3,8-diene-5,10-dione 10-Ethylene Acetal at the Conjugated Carbon-Carbon Double Bond. Australian Journal of Chemistry. 47: 963.

Burnes P, Cristiano D, Glover MR, Tsanaktsidis J. 1994. A Convenient, Regiospecific Synthesis of Dimethyl 4-Oxocyclopentane-1,3-dicarboxylate. Australian Journal of Chemistry. 47: 1811.

Lowe DA, Moorhouse CJ, Walter JM, Tsanaktsidis J. 1994. A New Approach to Alkylated Cubanes: The Synthesis of Dimethyl 2-Methylcubane-1,4-dicarboxylateAustralian. Journal of Chemistry. 47: 1647.

Maxwell BJ, Schiesser CH, Smart BA, Tsanaktsidis J. 1994. Ab initio Study of the Homolytic Additions of Aminyl and Ammoniumyl Cation Radicals to Alkenes. Journal of Chemical Society Perkin Transactions 2. 2385.

Beckwith ALJ, Maxwell BJ, Tsanaktsidis J. 1991. The Generation of Aminyl Radicals from Sulfenamides. Australian Journal of Chemistry. 44: 1809.

Eaton PE, Tsanaktsidis J. 1990. The Reactions of 1,4-Dihalocubanes with Organolithiums. The Case of 1,4-Cubadiyl. Journal of the American Chemical Society. 112: 876.

Reddy DS, Maggini M, Tsanaktsidis J, Eaton PE. 1990. Direct Radical Substitution on the Cubane Skeleton. Tetrahedron Letters. 31: 805.

Della EW, Taylor DK, Tsanaktsidis J. 1990. Unusual Bridgehead Reactivity: Formation of [1.1.1]Propellane by 1,3-Dehydrobromination of 1-Bromobicyclo[1.1.1]pentane. Tetrahedron Letters. 31: 5219.

Della EW, Tsanaktsidis J. 1989. The Synthesis of Bridgehead Halides by the Barton Decarboxylation Procedure. Australian Journal of Chemistry. 42: 61.

Tsanaktsidis J, Eaton PE. 1989. Synthesis of Iodocubanes by Decarboxylative Iodination. Tetrahedron Letters. 30: 6976.

Della EW, Tsanaktsidis J. 1988. Synthesis of Some Bridgehead Trimethylsilylpolycycloalkanes. Silicon-29 NMR Chemical Shifts and 29Si-13C Coupling Constants. Organometallics. 7: 1178.

Della EW, Tsanaktsidis J. 1988. A Convenient Synthesis of Fluorotrimethylsilane. Synthesis. 407.

Della EW, Pigou PE, Tsanaktsidis J. 1987. Enhanced Solvolytic Reactivity of 1-Bromobicyclo[3.3.1]heptane: Intermediacy of a Stabilised Bridgehead Carbenium Ion. Journal of the Chemical Society, Chemical Communications. 833.

Della EW, Tsanaktsidis J. 1986. Decarboxylation of Bridgehead Carboxylic Acids by the Barton Procedure. Australian Journal of Chemistry. 39: 2061.

Della EW, Tsanaktsidis J. 1985. Synthesis of Bridgehead-Bridgehead Substituted Bicycloalkanes. Australian Journal of Chemistry. 38: 1705.