Chemical synthesis of the tetrasaccharide repeating unit of the O-antigen from halophilic Salinicola salarius HO-14

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2026-04-01 Epub Date: 2026-01-16 DOI:10.1016/j.carres.2026.109813

Bijoy Rudra , Subrata Das , Balaram Mukhopadhyay

引用次数: 0

Abstract

Total chemical synthesis of the tetrasaccharide repeating unit of the O-antigen from the halophilic bacterium Salinicola salarius HO-14 in the form of its 2-aminoethyl glycoside is reported. Partially protected monosaccharide synthons are prepared from the commercially available d-mannose and l-rhamnose through rational protecting group manipulations. Sequential stereoselective glycosylations through activation of the thioglycoside using NIS and TMSOTf gave the target tetrasaccharide. The crucial 1,2-cis rhamnosidic linkage is formed by the use of hydrogen bond assisted aglycon delivery. The conjugation ready target tetrasaccharide is attractive for further glycoconjugate formation.

Abstract Image

查看原文本刊更多论文

嗜盐盐菌HO-14 o抗原四糖重复单元的化学合成。

报道了嗜盐细菌Salinicola salarius HO-14中o抗原的四糖重复单元的全化学合成，其形式为2-氨基乙基糖苷。从市售的d-甘露糖和l-鼠李糖中通过合理的保护基团操作制备部分保护的单糖合成物。通过使用NIS和TMSOTf激活巯基糖苷进行顺序立体选择性糖基化，得到目标四糖。关键的1,2-顺式鼠李糖键是通过氢键辅助糖苷传递形成的。偶联的目标四糖对进一步的糖偶联形成具有吸引力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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".