{"title":"Stereocontrolled Synthesis of a Heptose- and Kdo-Containing Common Inner-Core Trisaccharide of Lipopolysaccharides from Multiple Pathogenic Bacteria","authors":"Jiawei Li, Runing Gao, Tianhui Hao, Tiehai Li","doi":"10.1055/a-2301-2358","DOIUrl":null,"url":null,"abstract":"<p>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-<sc>d</sc>-<i>manno</i>-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.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"28 1","pages":""},"PeriodicalIF":1.7000,"publicationDate":"2024-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/a-2301-2358","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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.
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。
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.