Automated solid-phase synthesis of oligosaccharides

Science. 2001 Feb 23;291(5508):1523-7. doi: 10.1126/science.1057324. Epub 2001 Feb 1.

Abstract

Traditionally, access to structurally defined complex carbohydrates has been very laborious. Although recent advancements in solid-phase synthesis have made the construction of complex oligosaccharides less tedious, a high level of technical expertise is still necessary to obtain the desired structures. We describe the automated chemical synthesis of several oligosaccharides on a solid-phase synthesizer. A branched dodecasaccharide was synthesized through the use of glycosyl phosphate building blocks and an octenediol functionalized resin. The target oligosaccharide was readily obtained after cleavage from the solid support. Access to certain complex oligosaccharides now has become feasible in a fashion much like the construction of oligopeptides and oligonucleotides.

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

  • Automation
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chemistry, Organic / instrumentation
  • Chemistry, Organic / methods
  • Glucans / chemical synthesis
  • Glucans / chemistry
  • Glycosylation
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry*
  • Oligosaccharides / isolation & purification
  • Polymers
  • Resins, Plant
  • Temperature

Substances

  • Glucans
  • Oligosaccharides
  • Polymers
  • Resins, Plant