Regioselective syntheses of beta-N-linked glycoaminoacids and glycopeptides

J Org Chem. 2008 Jan 18;73(2):511-6. doi: 10.1021/jo7018637. Epub 2007 Dec 19.

Abstract

Acylation of tetra-O-pivaloyl-beta-D-galactopyranosylamine 2 by readily available N- (Cbz or Fmoc-alpha-aminoacyl) benzotriazoles under microwave irradiation proceeded diastereoselectively to give beta-N-glycoaminoacids 3a-d, (3c+3c') (compound numbers written within brackets represent a racemate or a diastereomeric mixture; compound numbers without brackets represent a single enantiomer) (83-92%), and glycosylated asparagine building block 9 (65%). N-Cbz-Protected peptidoylbenzotriazoles 4a-c similarly afforded beta-N-glycodipeptides 5a-c (76-81%). Regiospecific beta-N-linkage formation was established by 1D and 2D NMR techniques for 3b.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Amino Acids / radiation effects
  • Glycopeptides / chemical synthesis*
  • Glycopeptides / chemistry
  • Glycopeptides / radiation effects
  • Magnetic Resonance Spectroscopy / methods
  • Microwaves
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amino Acids
  • Glycopeptides