1-N-glycyl beta-oligosaccharide derivatives as stable intermediates for the formation of glycoconjugate probes

Biochemistry. 1992 Nov 10;31(44):10724-32. doi: 10.1021/bi00159a012.

Abstract

Incubation of reducing sugars in ammonium bicarbonate was found to be a simple procedure for the formation of beta-D-glycosylamines of purified complex oligosaccharides in 70-80% yield. These provide valuable intermediates for the synthesis of a wide range of oligosaccharide probes and derivatives by acylation of the 1-amino function. The 1-amino function showed different rates of reactivity with different reagents. In general, interactions with large ring systems such as the fluorophores dansyl chloride and carboxyfluorescein gave 10-20% yields of products, which consisted of mixtures of both anomeric forms, whereas smaller acylating reagents gave near-quantitative yields of the desired beta-D-derivatives. Steric effects may explain differences in reactivity. N-Chloroacetamido derivatives could be obtained in high yield with retention of the beta-anomeric configuration. Subsequent ammonolysis of the chloroacetamido function afforded the corresponding N-glycyl beta-derivatives. The linker thereby introduced retains the amino function, possesses the useful properties of fixed anomeric configuration, improved stability, and uniform reactivity with a variety of reagents, and is structurally analogous to an asparagine side chain. The potential therefore exists for the generation of oligosaccharide derivatives tailored for different applications.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / chemistry
  • Acylation
  • Animals
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chromatography, High Pressure Liquid
  • Dansyl Compounds / chemistry
  • Fluoresceins / chemistry
  • Glycoconjugates / chemical synthesis
  • Glycoconjugates / chemistry*
  • Glycosylation
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis
  • Oligosaccharides / chemistry*
  • Swine

Substances

  • Dansyl Compounds
  • Fluoresceins
  • Glycoconjugates
  • Oligosaccharides
  • 6-carboxyfluorescein
  • dansyl chloride
  • Acetylglucosamine