A strategy for the solid-phase synthesis of oligosaccharides

Science. 1993 May 28;260(5112):1307-9. doi: 10.1126/science.8493573.

Abstract

Repeating glycosidic linkages of oligosaccharides can be synthesized by solid-phase methods. Glycals were attached to a polystyrene copolymer with a silyl ether bond and were activated to function as glycosyl donors with 3,3-dimethyldioxirane. Glycosidation was performed by reactions with a solution-based acceptor (itself a glycal). Excess acceptor and promoter were removed by rinsing after each coupling, and the desired oligosaccharides were then easily obtained from the polymer by the addition of tetra-n-butylammonium fluoride. By this method, glycosidations are stereospecific and interior deletions are avoided.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Epoxy Compounds / chemistry
  • Glycosylation
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Polystyrenes

Substances

  • Epoxy Compounds
  • Oligosaccharides
  • Polystyrenes
  • dimethyldioxirane