Asymmetric reductions of ethyl 2-(benzamidomethyl)-3-oxobutanoate by yeasts

被引：18

作者：

Gandolfi, Raffaella ^{[1
]}

Cesarotti, Edoardo ^{[2
]}

Molinari, Francesco ^{[3
]}

Romano, Diego ^{[3
]}

Rimoldi, Isabella ^{[2
]}

机构：

[1] Univ Milan, Inst Organ Chem A Marchesini, I-20133 Milan, Italy

[2] Dept Inorgan Metallorgan & Analyt Chem L Malatest, I-20133 Milan, Italy

[3] Dept Food Sci & Microbiol, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 04期

关键词：

BIOCATALYTIC KETONE REDUCTION; BETA-AMINO ACIDS; DIASTEREOSELECTIVE REDUCTION; MICROBIAL REDUCTION; BAKERS-YEAST; STEREOCHEMICAL CONTROL; KLUYVEROMYCES-MARXIANUS; CHIRAL ALCOHOLS; POWERFUL TOOL; HYDROGENATION;

D O I：

10.1016/j.tetasy.2009.02.023

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The stereoselective reduction of ethyl 2-(benzamidomethyl)-3-oxobutanoate 1 using yeasts was investigated among a restricted number (12) of yeasts. Kluyveromyces marxianus var. lactis CL69 diastereoselectively produced (2R,3S)-ethyl 2-(benzamidomethyl)-3-hydroxybutanoate 2. whereas Pichia glucozyma CBS 5766 gave (2S,3S)-2 as the major stereoisomer. The biotransformations were independently optimized for minimizing by-product formation and maximizing the diastereoselectivity. Under optimized conditions, K. marxianus var. lactis CL 69 gave the (2R,3S)-ethyl 2-(benzamidomethyl)-3-hydroxybutanoate 2 with ee > 99% and de = 98%, while P. glucozyma CBS 5766 allowed for the production of (2S,3S)-2 with ee > 99% and de = 86%. (c) 2009 Elsevier Ltd. All rights reserved.

引用

页码：411 / 414

页数：4

共 32 条

[21] STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .16. STEREOCHEMICAL CONTROL IN DIASTEREOSELECTIVE REDUCTION WITH BAKERS-YEAST [J].