Post-synthesis incorporation of a lipidic side chain into a peptide on solid support

J Pept Sci. 2002 Nov;8(11):601-14. doi: 10.1002/psc.420.

Abstract

A new strategy for the synthesis of lipopeptides has been developed. Using Weinreb (N-methoxy, N-methyl) amide as an aldehyde function precursor on the side chains of Asp or Glu residues, this new strategy avoids the synthesis of a lipidic amino acid residue before its incorporation in the peptide sequence. The aldehyde generated on the solid support can react with ylides leading to unsaturated or saturated side chains or with various nucleophiles to yield non-coded amino acid residues incorporated into the sequence.

MeSH terms

  • Benzhydryl Compounds*
  • Chromatography, Thin Layer
  • Lipids / chemistry*
  • Lipoproteins / chemical synthesis*
  • Lipoproteins / chemistry
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Protein Conformation
  • Solutions

Substances

  • 4-methylbenzhydrylamine resin
  • Benzhydryl Compounds
  • Lipids
  • Lipoproteins
  • Peptides
  • Solutions