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Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles

Research output: Contribution to journalArticle

Kate Lauder, Silvia Anselmi, James D. Finnigan, Yuyin Qi, Simon J. Charnock, Daniele Castagnolo

Original languageEnglish
Pages (from-to)10422-10426
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number46
DOIs
Accepted/In press1 Jan 2020
Published17 Aug 2020

King's Authors

Abstract

The enantioselective synthesis of α-thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α-thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good-to-excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.

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