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

Autor:	Kate Lauder, Daniele Castagnolo, Simon J. Charnock, Yuyin Qi, Silvia Anselmi, James Finnigan
Rok vydání:	2020
Předmět:	biocatalysis Nitrile thiocarboxylic acid 010402 general chemistry 01 natural sciences Nitrilase Catalysis Kinetic resolution dynamic kinetic resolution chemistry.chemical_compound thionitrile Organic chemistry Racemization chemistry.chemical_classification nitrilase 010405 organic chemistry Chemistry Communication Organic Chemistry Enantioselective synthesis General Chemistry Communications 0104 chemical sciences Thiocarboxylic acid Biocatalysis Enantiomer
Zdroj:	Chemistry (Weinheim an Der Bergstrasse, Germany)
ISSN:	1521-3765
Popis:	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. Nitrilase biocatalysts catalyse the dynamic kinetic resolution (DKR) of α‐thionitriles affording enantiomerically pure α‐thiocarboxylic acids under mild conditions. The DKR is favoured by the ammonia formed in situ during the biotransformation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::86591ff7a1ba0cacf954757bce5fc1e4 https://pubmed.ncbi.nlm.nih.gov/32239730 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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