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Deracemization of Racemic Amines to Enantiopure ( R )‐ and ( S )‐amines by Biocatalytic Cascade Employing ω‐Transaminase and Amine Dehydrogenase
Author(s) -
Yoon Sanghan,
Patil Mahesh D.,
Sarak Sharad,
Jeon Hyunwoo,
Kim GeonHee,
Khobragade Taresh P.,
Sung Sihyong,
Yun Hyungdon
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900080
Subject(s) - enantiopure drug , amine gas treating , enantiomeric excess , chemistry , amination , enantioselective synthesis , reductive amination , deamination , biocatalysis , transaminase , enantiomer , organic chemistry , stereoselectivity , combinatorial chemistry , ketone , catalysis , enzyme , reaction mechanism
A one‐pot deracemization strategy for α‐chiral amines is reported involving an enantioselective deamination to the corresponding ketone followed by a stereoselective amination by enantiocomplementary biocatalysts. Notably, this cascade employing a ω‐transaminase and amine dehydrogenase enabled the access to both ( R )‐and ( S )‐amine products, just by controlling the directions of the reactions catalyzed by them. A wide range of ( R )‐and ( S )‐amines was obtained with excellent conversions (>80 %) and enantiomeric excess (>99 % ee ). Finally, preparative scale syntheses led to obtain enantiopure ( R )‐ and ( S )‐ 13 with the isolated yields of 53 and 75 %, respectively.