Chemo-enzymatic synthesis of unnatural amino acids

Archer, Ian, Arnold, S. Alison, Carr, Reuben, Fotheringham, Ian, Speight, Robert, & Taylor, Paul (2009) Chemo-enzymatic synthesis of unnatural amino acids. In Soloshonok, V.A. & Izawa, K. (Eds.) Asymmetric Synthesis and Application of α-Amino Acids. American Chemical Society, pp. 322-336.

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A general chemo-enzymatic process has been developed to prepare enantiomerically pure L- and D-amino acids in high yield by deracemisation of racemic starting materials. The method has been developed from initial academic studies to be a robust, scalable industrial process. Unnatural amino acids, in high optical purity, are a rapidly growing class of intermediates required for pharmaceuticals, agrochemicals and other fine chemical applications. However, no single method has proven sufficiently adaptable to prepare these compounds generally at large scale. Our approach uses an enantioselective oxidase biocatalyst and a non-selective chemical reducing agent to effect the stereoinversion of one enantiomer and can result in an enantiomeric excess of > 99 % from a starting racemate, and product yields over 90 %. The current approach compares very favourably to resolution methods which have a maximum single pass yield of 50 %. Efficient methods have been developed to adapt the biocatalyst used in this process towards new target compounds and to optimise key factors which improve the process efficiency and offer competitive economics at scale.

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ID Code: 72185
Item Type: Book Chapter
Additional URLs:
DOI: 10.1021/bk-2009-1009.ch020
ISBN: 9780841269743
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000)
Australian and New Zealand Standard Research Classification > BIOLOGICAL SCIENCES (060000)
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 28 May 2014 23:14
Last Modified: 26 Oct 2015 16:28

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