Deracemization of Racemic Amines to Enantiopure ( R )‐ and ( S )‐amines by Biocatalytic Cascade Employing ω‐Transaminase and Amine Dehydrogenase | Zendy

Yoon Sanghan | Zendy; Patil Mahesh D. | Zendy; Sarak Sharad | Zendy; Jeon Hyunwoo | Zendy; Kim GeonHee | Zendy; Khobragade Taresh P. | Zendy; Sung Sihyong | Zendy; Yun Hyungdon | Zendy

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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.

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