Application of the trichloroacetimidate method to the synthesis of glycopeptides of the mucin type containing a beta-D-Galp-(1----3)-D-GalpNAc unit

Carbohydr Res. 1987 Jul 1:164:265-76. doi: 10.1016/0008-6215(87)80135-0.

Abstract

Mucin-type O-glycopeptides containing the beta-D-Galp-(1----3)-D-GalpNAc disaccharide core unit, which is also the T-antigenic determinant, were synthesized from D-galactose, 2-azido-2-deoxy-D-galactose, 2-azido-2-deoxylactose, and L-serine precursors by applying the trichloroacetimidate method. Thus, beta-D-Galp-(1----3)-alpha-D-GalpNAc-(1----3)-Ser (1) and beta-D-Galp-(1----4)-beta-D-GlcpNAac-(1----6)-[beta-D-Galp-(1----3 )]-alpha-D-GalpNAc-(1----3)-Ser (2) were obtained. A protected precursor of 2 having free OH groups at C-4 and C-6 of the inner sugar unit is a valuable intermediate for the synthesis of further O-glycopeptides of this core-unit type.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylgalactosamine*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Galactosamine* / analogs & derivatives
  • Galactose*
  • Glycopeptides / chemical synthesis*
  • Imidoesters
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mucins / chemical synthesis*
  • Optical Rotation

Substances

  • Glycopeptides
  • Imidoesters
  • Indicators and Reagents
  • Mucins
  • Galactosamine
  • Acetylgalactosamine
  • Galactose