A simple synthesis of 2-keto-3-deoxy-D-erythro-hexonic acid isopropyl ester, a key sugar for the bacterial population living under metallic stress

被引：3
|
作者：
Grison, Claire M. [1 ]
Renard, Brice-Loic [2 ]
Grison, Claude [2 ]
机构：
[1] Univ Paris 11, Equipe Synthese Organ & Methodol, ICMMO UMR 8182, Bat 420,15 Rue Georges Clemenceau, F-91405 Orsay, France
[2] CEFE UMR 5175, F-34293 Montpellier 5, France
来源：
BIOORGANIC CHEMISTRY | 2014年 / 52卷
关键词：
2-Keto-3-deoxy-D-erythro-hexonic acid; isopropyl ester; Swern oxidation; Modified Darzens reaction; One-pot isomerization-reduction reaction; Entner Doudoroff pathway; Heavy-metal resistant rhizobia; CATALYTIC MECHANISM;
D O I：
10.1016/j.bioorg.2013.11.006
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
2-Keto-3-deoxy-D-erythro-hexonic acid (KDG) is the key intermediate metabolite of the Entner Doudoroff (ED) pathway. A simple, efficient and stereoselective synthesis of KDG isopropyl ester is described in five steps from 2,3-O-isopropylidene-D-threitol with an overall yield of 47%. KDG isopropyl ester is studied as an attractive marker of a functional Entner Doudoroff pathway. KDG isopropyl ester is used to promote growth of ammonium producing bacterial strains, showing interesting features in the remediation of heavy-metal polluted soils. (C) 2013 Elsevier Inc. All rights reserved.
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页码：50 / 55
页数：6
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