One-Pot Transformation of Ketoximes into Optically Active Alcohols and Amines by Sequential Action of Laccases and Ketoreductases or ω-Transaminases

被引：15

作者：

Cordeiro, Raquel S. Correia ^{[1
,2
]}

Rios-Lombardia, Nicolas ^{[1
]}

Moris, Francisco ^{[1
]}

Kourist, Robert ^{[3
]}

Gonzalez-Sabin, Javier ^{[1
]}

机构：

[1] EntreChem SL, Vivero Ciencias Salud, Oviedo 33011, Spain

[2] Ruhr Univ Bochum, Jr Res Grp Microbial Biotechnol, Fac Biol & Biotechnol, D-44780 Bochum, Germany

[3] Graz Univ Technol, Petersgasse 14, A-8010 Graz, Austria

来源：

CHEMCATCHEM | 2019年 / 11卷 / 04期

基金：

欧盟地平线“2020”;

关键词：

one-pot reaction; oxime; alcohol dehydrogenase; transaminase; enzymatic cascade; SYNTHETIC APPLICATION; CASCADE CATALYSIS; DEHYDROGENASE; CAERULOMYCIN; BIOCATALYSIS; STEREOSELECTIVITY; ISOMERIZATION; PURIFICATION; COMBINATION; SYSTEMS;

D O I：

10.1002/cctc.201801900

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An enzymatic one-pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase-catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (omega-transaminase, omega-TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and overall conversions ranging from 83 to >99 % for alcohols and 70 to >99 % for amines. Likewise, the employment of exclusively 1 % (w/w) of Cremophor (R), a polyethoxylated castor oil, as co-solvent enabled to reach concentrations up to 100 mM in the chiral alcohols cascade.

引用

页码：1272 / 1277

页数：6

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