Synthesis of potassium (2R)-2-O-α-D-glucopyranosyl-(1→6)-α-D-glucopyranosyl-2,3-dihydroxypropanoate a natural compatible solute

被引:27
|
作者
Lourenco, Eva C. [1 ]
Maycock, Christopher D. [1 ,2 ]
Ventura, M. Rita [1 ]
机构
[1] Univ Nova Lisboa, Inst Tecnol Quim & Biol, P-2780901 Oeiras, Portugal
[2] Univ Lisbon, Fac Ciencias, Dept Quim & Bioquim, P-1749016 Lisbon, Portugal
关键词
alpha-Glucosylation; Hypersolutes; Glucosyl glycerate; Thioglycosides; Glyceric acid; PROMOTED REACTIONS; SOLID-PHASE; POLYSACCHARIDE; THIOGLYCOSIDES; TRISACCHARIDE; GLYCOSIDES; ESTERS;
D O I
10.1016/j.carres.2009.06.037
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
Ethyl 6-O-acetyl-2,3,4-tribenzyl-1-thio-D-glucopyranoside, as a mixture of anomers, was employed for the stereoselective synthesis of the potassium salt of (2R)-2-O-alpha-D-glucopyranosyl-(1 -> 6)-alpha-D-glucopyranosyl-2,3-dihydroxypropanoic acid (alpha-D-glucosyl-(1 -> 6)-alpha-D-glucosyl-(1 -> 2)-D-glyceric acid, GGG), a recently isolated compatible solute. The alpha-anomer was by far the major product of both glycosylation reactions using NIS/TfOH as activator. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2073 / 2078
页数:6
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