Synthesis of N-Fmoc-O- (N'-Boc-N'-methyl)-aminohomoserine, an amino acid for the facile preparation of neoglycopeptides

J Org Chem. 2003 Jan 10;68(1):195-7. doi: 10.1021/jo026641p.

Abstract

The synthesis of N-Fmoc-O-(N'-Boc-N'-methyl)-aminohomoserine in 35% overall yield from l-homoserine is described. This amino acid can be efficiently incorporated into peptides using Fmoc-chemistry-based solid-phase peptide synthesis, and the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The synthesis of this derivative greatly expands the availability of a previously developed neoglycopeptide synthesis strategy.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Glycoproteins / chemical synthesis*
  • Homoserine / analogs & derivatives
  • Homoserine / analysis
  • Homoserine / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Peptides / chemical synthesis*

Substances

  • Glycoproteins
  • N-Fmoc-O- (N'-Boc-N'-methyl)-aminohomoserine
  • Peptides
  • Homoserine