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Deracemisation of α‐Chiral Primary Amines by a One‐Pot, Two‐Step Cascade Reaction Catalysed by ω‐Transaminases
Author(s) -
Koszelewski Dominik,
Clay Dorina,
Rozzell David,
Kroutil Wolfgang
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801265
Subject(s) - chemistry , amine gas treating , kinetic resolution , ketone , enantiomeric excess , enantiomer , transaminase , stereochemistry , biocatalysis , organic chemistry , enantioselective synthesis , catalysis , reaction mechanism , enzyme
Racemic α‐chiral primary amines were deracemised to optically pure amines in up to >99 % conversion and >99 % ee within 48 h. The deracemisation was a result of a stereoinversion of one amine enantiomer; the formal stereoinversion was achieved by a one‐pot, two‐step procedure: in the first step, kinetic resolution of the chiral racemic amine was performed by employing a ω‐transaminase to yield an intermediate ketone and the remaining optically pure amine; in the second step, the ketone intermediate was stereoselectively transformed into the amine by employing alanine as the amine donor and a ω‐transaminase displaying opposite stereopreference than the ω‐transaminase in the first step. In the second step, lactate dehydrogenase was used to remove the side product pyruvate to shift the unfavourable reaction equilibrium to the product side. Depending on the order of the enantiocomplementary enzymes employed in the cascade, the ( R ), as well as the ( S ), enantiomer was accessible.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)