Formal Asymmetric Biocatalytic Reductive Amination

All for one: A combination of three biocatalysts (ω‐transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α‐chiral unprotected amine through a formal stereoselect...

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Published inAngewandte Chemie (International ed.) Vol. 47; no. 48; pp. 9337 - 9340
Main Authors Koszelewski, Dominik, Lavandera, Iván, Clay, Dorina, Guebitz, Georg M, Rozzell, David, Kroutil, Wolfgang
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2008
WILEY‐VCH Verlag
Wiley
Subjects
Amination
amines
Amines - chemistry
Amines - metabolism
asymmetric catalysis
Biocatalysis
cascade reactions
Chemistry
Chemistry, Multidisciplinary
Ketones - chemistry
Oxidation-Reduction
Physical Sciences
reductive amination
Science & Technology
Stereoisomerism
D-AMINO ACIDS
ENANTIOSELECTIVE SYNTHESIS
amines
MICROBIAL SYNTHESIS
asymmetric catalysis
ALPHA-KETO ACIDS
biocatalysis
CHIRAL AMINES
cascade reactions
SUBSTRATE-SPECIFICITY
reductive amination
KINETIC RESOLUTION
PYRUVATE TRANSAMINASE
OMEGA-TRANSAMINASE
ORGANOCATALYTIC TRANSFER HYDROGENATION
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Summary:All for one: A combination of three biocatalysts (ω‐transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α‐chiral unprotected amine through a formal stereoselective reductive amination (see scheme). Only ammonia and the reducing agent (formate) are consumed during this reaction.
Bibliography:http://dx.doi.org/10.1002/anie.200803763
Financial support by the FFG and the Province of Styria is gratefully acknowledged. Codexis is thanked for providing various enzymes.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200803763