Preparative deracemization of unnatural amino acids

Archer, I., Fotheringham, I., Carr, R., Speight, R., & Turner, N.J. (2006) Preparative deracemization of unnatural amino acids. Biochemical Society Transactions, 34(2), pp. 287-290.

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Unnatural amino acids are a growing class of intermediates required for pharmaceuticals, agrochemicals and other industrial products. However, no single method has proven sufficiently versatile to prepare these compounds broadly at scale. To address this need, we have developed a general chemoenzymatic process to prepare enantiomerically pure L- and D-amino acids in high yield by deracemization of racemic starting materials. This method involves the concerted action of 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 the starting racemate, and product yields of over 90%. This approach compares very favourably with resolution processes, which have a maximum single-pass yield of 50%. We have developed efficient methods to adapt the process towards new target compounds and to optimize key factors that influence process efficiency and offer competitive economics at scale.

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25 citations in Web of Science®

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ID Code: 70985
Item Type: Journal Article
Refereed: Yes
Additional URLs:
Keywords: biocatalysis, biotransformation, chiral amine, deracemization, stereoinversion, unnatural amino acid
DOI: 10.1042/BST20060287
ISSN: 1470-8752
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 04 May 2014 22:49
Last Modified: 12 May 2014 04:52

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