Direct peptide lipidation through thiol-ene coupling enables rapid synthesis and evaluation of self-adjuvanting vaccine candidates

Angew Chem Int Ed Engl. 2013 Sep 27;52(40):10616-9. doi: 10.1002/anie.201305620. Epub 2013 Aug 12.

Abstract

A radical lipidation: Application of a novel thiol-ene lipidation enables the one-step synthesis of self-adjuvanting antigenic peptides as vaccine candidates. The resultant monoacyl lipopeptides are shown to activate monocytes in a robust manner.

Keywords: adjuvants; immunology; peptides; thiol-ene reaction; vaccines.

MeSH terms

  • Antigens / chemistry
  • Antigens / immunology
  • Humans
  • Lipopeptides / chemical synthesis*
  • Lipopeptides / immunology*
  • Peptides / chemistry
  • Peptides / immunology
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry
  • Vaccines / chemical synthesis*
  • Vaccines / pharmacology

Substances

  • Antigens
  • Lipopeptides
  • Peptides
  • Sulfhydryl Compounds
  • Vaccines