大肠杆菌 O50 O 型抗原可连接的四糖重复单元的化学合成

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-04-10 DOI:10.1016/j.carres.2025.109485

Sunil K. Yadav, Somnath Yadav

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引用次数: 0

摘要

大肠杆菌是一种杆状革兰氏阴性菌，因引发多种人类感染而臭名昭著。本研究首次利用氨基乙基连接体扩增革兰氏阴性菌大肠杆菌O50细胞壁四糖重复单元，采用线性[1+1+1+1]和一锅[1+1+2]两种方法合成，后一种方法产量更高。作为氨基乙基连接剂，可进一步用于生物用途；l-鼠李糖和d-葡萄糖胺之间具有挑战性的顺式（1→4）-β-糖苷键在这里进行了高立体控制。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Chemical synthesis of conjugation-ready tetrasaccharide repeating unit of Escherichia coli O50 O-antigen

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Chemical synthesis of conjugation-ready tetrasaccharide repeating unit of Escherichia coli O50 O-antigen

Escherichia coli is a rod-shaped Gram-negative bacterium notorious for provoking diverse human infections. In this study, we report the first total synthesis of tetrasaccharide repeating unit of the cell wall of Gram-negative bacteria Escherichia coli O50 augmented with aminoethyl linker, employing both linear [1+1+1+1] and one-pot [1+1+2] approaches, and later one providing the better yield. As an aminoethyl linker, it can be further utilized for biological purposes; the challenging cis (1 → 4)-β-glycosidic linkage between l-rhamnose and d-glucosamine is addressed here with high stereo control.

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".