Total synthesis of the trisaccharide repeating unit of the O-polysaccharide of Pragia fontium 97U124

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-04-17 DOI:10.1016/j.carres.2025.109494

Balasaheb K. Ghotekar, Suvarn S. Kulkarni

引用次数: 0

Abstract

Herein, we report the first total synthesis of a densely functionalized trisaccharide repeating unit of Pragia fontium 97U124. The presence of rare deoxy amino sugars namely C4–N-glyceroyl-d-bacillosamine and l-fucosamine, two consecutive 1,2-cis linkages, five nitrogen dispensed over three rings and orthogonal functionality of amines makes the trisaccharide synthesis a challenging task. The total synthesis of target molecule was completed via a longest linear sequence of 22 steps in 5.1 % overall yield starting from d-mannose.

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Pragia fontium 97U124 o -多糖三糖重复单元的全合成

在这里，我们报道了Pragia fontium 97U124的一个密集功能化的三糖重复单元的首次全合成。稀有脱氧氨基糖c4 - n -甘油-d-杆菌胺和l- focusamine的存在，两个连续的1,2-顺式键，五个氮分布在三个环上以及胺的正交官能团的存在使得三糖的合成成为一项具有挑战性的任务。从d-甘露糖开始，经过最长的22步线性合成，总收率为5.1%。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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".