Capsular polysaccharide of Streptococcus pneumoniae type 19F: synthesis of the repeating unit

Carbohydr Res. 1998 Oct;311(4):171-81. doi: 10.1016/s0008-6215(98)00218-3.

Abstract

A new and more versatile synthesis of beta-D-ManpNAc-(1-->4)-alpha-D-Glcp-(1-->2)-alpha-L-Rhap, the trisaccharide repeating unit of the Streptococcus pneumoniae type 19F capsular polysaccharide, is described. The present approach allows a simple access to different fragments containing the trisaccharide and the conjugation of the product(s) to a protein through the selective manipulation of the anomeric position at the reducing end and of the HO-4 function at the nonreducing end. The synthetic scheme shows an efficient application of the sulfoxide method for the stereoselective and high yielding formation of the glycosidic linkages.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Capsules
  • Carbohydrate Sequence
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Molecular Sequence Data
  • Polysaccharides, Bacterial / chemistry*
  • Streptococcus pneumoniae / chemistry*

Substances

  • Polysaccharides, Bacterial
  • capsular polysaccharide 19F