Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans

被引：5

作者：

Wang, Liming ^{[1
]}

Berni, Francesca ^{[1
]}

Enotarpi, Jacopo ^{[1
]}

Overkleeft, Hermen S. ^{[1
]}

van der Marel, Gijs ^{[1
]}

Codee, Jeroen D. C. ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, Einsteinweg 55, NL-2333 CC Leiden, Netherlands

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 11期

基金：

欧洲研究理事会;

关键词：

ALPHA-GLYCOSYLATION STRATEGY; PROPOSED FUNDAMENTAL STRUCTURE; GRAM-POSITIVE BACTERIA; LIPOTEICHOIC ACID; IN-SITU; OLIGOSACCHARIDE; KOJIBIOSE; FRAGMENT; DIMETHYLFORMAMIDE; CLEAVAGE;

D O I：

10.1039/d0ob00240b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective construction of 1,2-cis-glycosidic linkages is key in the assembly of biologically relevant glycans, but remains a synthetic challenge. Reagent-controlled glycosylation methodologies, in which external nucleophiles are employed to modulate the reactivity of the glycosylation system, have become powerful means for the construction of 1,2-cis-glycosidic linkages. Here we establish that nucleophilic additives can support the construction of alpha-1,2-glucans, and apply our findings in the construction of a d-alanine kojibiose functionalized glycerol phosphate teichoic acid fragment. This latter molecule can be found in the cell wall of the opportunistic Gram-positive bacterium, Enterococcus faecalis and represents a structural element that can possibly be used in the development of therapeutic vaccines and diagnostic tools.

引用

页码：2038 / 2050

页数：13

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