Total Synthesis of Trisaccharide Repeating Unit of O-Specific Polysaccharide of Pseudomonas fluorescens BIM B-582

Org Lett. 2018 Sep 21;20(18):5956-5959. doi: 10.1021/acs.orglett.8b02669. Epub 2018 Sep 6.

Abstract

The first total synthesis of the trisaccharide repeating unit of the O-specific polysaccharide of Pseudomonas fluorescens BIM B-582 is reported. This efficient synthesis involves consecutive 1,2- cis glycosylations including β-l-rhamnosylation and α selective coupling of rare 4-deoxy-d- xylo-hexose as the key steps. The synthetic trisaccharide is equipped with an aminopropyl linker at the reducing end to allow for conjugation to proteins and microarrays for further immunological studies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • O Antigens / chemistry*
  • Pseudomonas fluorescens / chemistry*
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry

Substances

  • O Antigens
  • Trisaccharides