Solid-phase synthesis of O-glycosylated Nalpha-Fmoc amino acids and analysis by high-resolution magic angle spinning NMR

J Comb Chem. 2004 Mar-Apr;6(2):214-9. doi: 10.1021/cc034005e.

Abstract

Direct O-glycosylation of amino acids bound to TentaGel resin with a number of glycosyl trichloroacetimidate donors results in high yields. The glycosylation reaction can be easily monitored by analyzing the bead-bound amino acids with high-resolution magic angle spinning (HR-MAS) NMR. These studies pave a new way for the construction of "one-bead one-compound" O-glycopeptide libraries with standard amino acid building blocks and appropriate glycosyl trichloroacetimidate donors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides
  • Amino Acids / analysis
  • Amino Acids / chemical synthesis*
  • Chloroacetates*
  • Fluorenes / analysis
  • Fluorenes / chemical synthesis*
  • Fucose / chemistry
  • Glycosylation
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism
  • Trichloroacetic Acid / chemistry

Substances

  • Acetamides
  • Amino Acids
  • Chloroacetates
  • Fluorenes
  • N(alpha)-fluorenylmethyloxycarbonylamino acids
  • Fucose
  • Trichloroacetic Acid
  • trichloroacetamide