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
收藏
页码：2038 / 2050
页数：13
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