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A Route to Polyprenol Pyrophosphate-Based Probes of O-Polysaccharide Biosynthesis in Klebsiella pneumoniae O2a

Author:
Sweeney, Ryan P., Lowary, Todd L.
Source:
Organic letters 2019 v.21 no.4 pp. 1050-1053
ISSN:
1523-7052
Subject:
Klebsiella pneumoniae, biosynthesis, diastereoselectivity, glycosylation, lipids, moieties, organic compounds, polysaccharides, serotypes
Abstract:
An approach for the assembly of polyprenol pyrophosphate-based probes of O-polysaccharide biosynthesis in Klebsiella pneumoniae serotype O2a is described. This convergent route features high-yielding, diastereoselective glycosylations and the late-stage installation of the polyprenol pyrophosphate moiety. Although applied to the synthesis of a nonasaccharide bearing a farnesyl group (1), the modular nature of the route makes it amenable to the synthesis of additional derivatives containing either larger glycans or different lipid domains.
Agid:
6310493