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Synlett
DOI: 10.1055/a-2301-2358
DOI: 10.1055/a-2301-2358
letter
Carbohydrate Chemistry in China
Stereocontrolled Synthesis of a Heptose- and Kdo-Containing Common Inner-Core Trisaccharide of Lipopolysaccharides from Multiple Pathogenic Bacteria
Financial support from the National Natural Science Foundation of China (22077130 and 22377134) and Shanghai Municipal Science and Technology Major Project is acknowledged.
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.
Key words
lipopolysaccharides - glycosylation - bacterial oligosaccharides - heptose - Kdo - trisaccharidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2301-2358.
- Supporting Information
Publication History
Received: 11 March 2024
Accepted after revision: 06 April 2024
Accepted Manuscript online:
06 April 2024
Article published online:
18 April 2024
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