Synthesis of mono- and disaccharide amino-acid derivatives for use in solid phase peptide synthesis

Glycoconj J. 1989;6(1):5-19. doi: 10.1007/BF01047886.

Abstract

N-Fluorenylmethyloxycarbonyl-protected serine and threonine derivatives, carrying O-glycosidically alpha- or beta-linked peracetylated beta-D-Galp-(1-3)-D-GalNAcp carbohydrate chains, were prepared. These derivatives are intended for use in solid phase glycopeptide synthesis. Suitably protected mono- and disaccharide thioglycosides were used as carbohydrate intermediates. These were activated by treatment with bromine to give the glycosyl bromides, which were then used in silver triflate-promoted glycosidations of N-fluorenylmethyloxycarbonyl amino-acid phenacyl esters. Removal of the phenacyl esters with zinc gave the target free acids.

MeSH terms

  • Amino Acids*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Disaccharides*
  • Glycopeptides / chemical synthesis*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Monosaccharides*
  • Optical Rotation
  • Peptides / chemical synthesis*

Substances

  • Amino Acids
  • Disaccharides
  • Glycopeptides
  • Indicators and Reagents
  • Monosaccharides
  • Peptides