Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors

Bioorg Med Chem. 2001 Jul;9(7):1857-69. doi: 10.1016/s0968-0896(01)00086-4.

Abstract

A series of D- and L-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These 'disaccharides', in which the acetyl moiety of the natural N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for beta(1-4)-galactosyl-transferase and alpha(1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides.

MeSH terms

  • Amides / chemistry*
  • Carbohydrates / chemical synthesis*
  • Carbohydrates / chemistry
  • Galactose / chemistry*
  • Galactosyltransferases / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • N-Acetyllactosamine Synthase / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry

Substances

  • Amides
  • Carbohydrates
  • Peptides
  • Galactosyltransferases
  • N-acetyllactosaminide alpha-1,3-galactosyltransferase
  • N-Acetyllactosamine Synthase
  • Galactose