Stereocontrolled Synthesis of a Heptose- and Kdo-Containing Common Inner-Core Trisaccharide of Lipopolysaccharides from Multiple Pathogenic Bacteria

IF 1.7 4区 化学 Q3 CHEMISTRY, ORGANIC
Synlett Pub Date : 2024-04-18 DOI:10.1055/a-2301-2358
Jiawei Li, Runing Gao, Tianhui Hao, Tiehai Li
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引用次数: 0

Abstract

Lipopolysaccharides (LPSs) are major virulence determinants in Gram-negative bacteria and are responsible for many pathophysiological processes during bacterial infections. However, the accessibility of LPS-associated oligosaccharides for infectious mechanism study and vaccine development remains challenging. We report an efficient stereocontrolled approach for the synthesis of a common inner-core trisaccharide containing difficult-to-access, rare, higher-carbon sugars: a heptose (Hep) and 3-deoxy-α-d-manno-oct-2-ulosonic acid (Kdo). Key features include comprehensive elaboration of a practical synthesis of versatile Hep and Kdo building blocks, and stereoselective assembly of an inner-core trisaccharide from multiple pathogenic bacteria.

Abstract Image

立体控制合成多种病原菌脂多糖中含有七聚糖和 Kdo 的共同内核三糖
脂多糖(LPSs)是革兰氏阴性细菌的主要毒力决定因素,是细菌感染期间许多病理生理过程的罪魁祸首。然而,将 LPS 相关寡糖用于感染机理研究和疫苗开发仍具有挑战性。我们报告了一种高效的立体控制方法,用于合成含有难以获得的稀有高碳糖:庚糖(Hep)和 3-脱氧-α-d-甘露辛-2-磺酸(Kdo)的常见内核三糖。主要特点包括全面阐述了多功能 Hep 和 Kdo 构建模块的实用合成方法,以及从多种病原菌中立体选择性地组装内核三糖。
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来源期刊
Synlett
Synlett 化学-有机化学
CiteScore
3.40
自引率
5.00%
发文量
369
审稿时长
1 months
期刊介绍: SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.
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