Synthesis of C-terminal glycopeptides from resin-bound glycosyl azides via a modified Staudinger reaction.

  title={Synthesis of C-terminal glycopeptides from resin-bound glycosyl azides via a modified Staudinger reaction.},
  author={J. Malkinson and R. Falconer and I. Toth},
  journal={The Journal of organic chemistry},
  volume={65 17},
The solid-phase synthesis of glycopeptides containing the sugar at the C-terminus is reported. The method is demonstrated on a model, the endogenous antinociceptive peptide Leu-enkephalin. 2,3,4-Tri-O-acetyl-1-azido-1-deoxy-beta-D-glucopyranuronic acid was synthesized and immobilized onto a variety of derivatized resins. Conjugation of the first amino acid was accomplished by reaction of the resin-bound glycosyl azide with an activated amino acid, in one step, via a modified Staudinger reaction… Expand
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