与君氏不动杆菌 65 株 O 型抗原多糖相对应的五糖重复单元与可连接的连接体的合成。

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY Carbohydrate Research Pub Date : 2024-10-22 DOI:10.1016/j.carres.2024.109295

Aniket Majhi, Samim Sahaji, Anup Kumar Misra

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引用次数: 0

摘要

我们以良好的收率直接合成了五糖，其连接臂与君氏不动杆菌 65 株的 O 型抗原多糖相对应。该合成是以硫代糖苷为糖基供体，在 N-iodosuccinimide (NIS) 和三氟甲基磺酸 (TfOH) 作为亲硫活化剂的组合存在下进行的。糖基化步骤的产率非常高，糖苷键的立体化学性质令人满意。利用一锅迭代糖基化策略还获得了五糖衍生物。

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Synthesis of the pentasaccharide repeating unit with a conjugation-ready linker corresponding to the O-antigenic polysaccharide of Acinetobacter junii strain 65

A straightforward synthesis of the pentasaccharide with a readily available linker arm corresponding to the O-antigenic polysaccharide of Acinetobacter junii strain 65 has been achieved in good yield. The synthesis has been carried out using thioglycosides as glycosyl donor in the presence of a combination of N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) as thiophilic activator. The yields of the glycosylation steps were very good with satisfactory stereochemistry at the glycosidic linkages. The pentasaccharide derivative has also been obtained using a one-pot iterative glycosylation strategy.

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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".