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B 族链球菌 VI 型荚膜多糖重复单元的唾液酸化五糖的合成。

Synthesis of the sialylated pentasaccharide repeating unit of the capsular polysaccharide of Streptococcus group B type VI.

机构信息

Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata, 700054, India.

Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata, 700054, India.

出版信息

Carbohydr Res. 2021 Apr;502:108294. doi: 10.1016/j.carres.2021.108294. Epub 2021 Mar 16.

DOI:10.1016/j.carres.2021.108294
PMID:33765475
Abstract

An efficient synthetic strategy has been developed for the synthesis of the sialic acid containing pentasaccharide repeating unit of the cell wall O-antigen of Streptococcus group B type VI strain involving stereoselective α-glycosylation of sialic acid thioglycoside derivative. Stereoselective glycosylation of glycosyl trichloroacetimidate derivatives and thioglycosides were carried out using perchloric acid supported over silica (HClO-SiO) as a solid acid catalyst. A panel of sialic acid donors has been screened for achieving satisfactory yield and stereochemical outcome of the glycosylation reaction.

摘要

现已开发出一种有效的合成策略,用于合成 B 族链球菌 VI 型菌株细胞壁 O-抗原的含唾液酸五糖重复单元,该策略涉及唾液酸硫糖苷衍生物的立体选择性α-糖苷化。使用负载在二氧化硅上的高氯酸(HClO-SiO)作为固体酸催化剂,对糖基三氯乙酰亚胺酯衍生物和硫糖苷进行立体选择性糖苷化。已经筛选了一系列唾液酸供体,以实现糖苷化反应的令人满意的产率和立体化学结果。

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