Synthesis of Lipopeptides by CLipPA Chemistry

Methods Mol Biol. 2021:2355:253-263. doi: 10.1007/978-1-0716-1617-8_19.

Abstract

Lipidation of polypeptides with a fatty acid to form N-linked lipopeptides can be a time consuming process due to the need to mask other reactive function groups present on the side chains of amino acids. Cysteine Lipidation on a Peptide or Amino acid (CLipPA) technology enables the direct lipidation of unprotected peptides containing a free thiol group to afford S-lipidated lipopeptides. A generalized procedure for the synthesis of S-lipopeptides is described which facilities rapid preparation of tens of analogs of lipopeptides from a single thiolated polypeptide precursor.

Keywords: CLipPA; Lipopeptides; S-lipidation; Thiol-ene.

MeSH terms

  • Amino Acids
  • Cysteine
  • Fatty Acids
  • Lipopeptides / chemistry*
  • Sulfhydryl Compounds

Substances

  • Amino Acids
  • Fatty Acids
  • Lipopeptides
  • Sulfhydryl Compounds
  • Cysteine