Asymmetric synthesis of (-)-fosfomycin and its trans-(1S,2S)-diastereomer using a biocatalytic reduction as the key step

被引：10

作者：

Marocco, Christian P. ^{[1
]}

Davis, Erik V. ^{[1
]}

Finnell, Julie E. ^{[1
]}

Phung-Hoang Nguyen ^{[1
]}

Mateer, Scott C. ^{[2
]}

Ghiviriga, Ion ^{[3
]}

Padgett, Clifford W. ^{[1
]}

Feske, Brent D. ^{[1
]}

机构：

[1] Armstrong Atlantic State Univ, Dept Chem & Phys, Savannah, GA 31419 USA

[2] Armstrong Atlantic State Univ, Dept Biol, Savannah, GA 31419 USA

[3] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 18-19期

基金：

美国国家科学基金会;

关键词：

ALDOSE REDUCTASE; ABSOLUTE-CONFIGURATION; FOSFOMYCIN; PHOSPHONOMYCIN; OLD; SELECTIVITY; EPOXIDATION; ASSIGNMENT; ANTIPODES; COMPLEXES;

D O I：

10.1016/j.tetasy.2011.10.009

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Fosfomycin is a gram positive and gram negative antibiotic that contains an asymmetric epoxide. An enzyme library was screened for its ability to reduce dimethyl(1-chloro-2-oxopropyl)phosphonate to the corresponding asymmetric chlorohydrin. Homology models were built in MOE, which were shown to accurately model the enzyme-substrate complex displaying the stereoselectivity that we observed. Two enzymes, YDR368w and YHR104w, were chosen for the scale up and synthesis of fosfomycin and its trans-(1S,2S)-diastereomer. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1784 / 1789

页数：6

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