First synthesis of the beta-D-rhamnosylated trisaccharide repeating unit of the O-antigen from Xanthomonas campestris pv. campestris 8004

J Org Chem. 2005 Sep 30;70(20):8064-70. doi: 10.1021/jo051153d.

Abstract

The trisaccharide repeating unit of the O-antigen of the lipopolysaccharide from Xanthomonas campestris pv. campestris 8004, a pathogen of cruciferous crops, presents some structural features that renders it a challenging synthetic target: the presence of a beta-D-rhamnosidic linkage, the steric crowd on a 1,2-cis-diglycosylated D-rhamnose, and finally the noncommercial availability of its monosaccharide constituents. The synthesis of this trisaccharide as methyl glycoside has been accomplished by exploiting a strategy whose key steps were the sequential beta-D-rhamnosylation with a 2-O-benzylsulfonyl-N-phenyltrifluoroacetimidate donor, debenzylsulfonylation, and coupling with a D-Fucp3NAc thioglycoside donor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Disaccharides / chemical synthesis
  • Disaccharides / chemistry
  • Models, Molecular
  • Molecular Sequence Data
  • O Antigens / chemistry*
  • Plant Diseases / microbiology
  • Rhamnose*
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry
  • Xanthomonas campestris / chemistry*
  • Xanthomonas campestris / pathogenicity

Substances

  • Disaccharides
  • O Antigens
  • Trisaccharides
  • Rhamnose