Chemical modifications of peptide sequences via S-alkylation reaction

Org Lett. 2013 Oct 18;15(20):5354-7. doi: 10.1021/ol402637d. Epub 2013 Oct 3.

Abstract

A chemoselective, convenient, and mild synthetic strategy to modify peptides on a cysteine sulfhydryl group is described. It simply requires activated molecular sieves to selectively promote S-alkylation in the presence of peptide nucleophilic functionalities. The procedure is easy to perform, fast, and provides high yields even in the case of poor electrophilic groups. Moreover, the method allows an efficient one-pot poly alkylation, proving that the sulfhydryl reactivity does not rely on its specific position within the peptide sequence.

MeSH terms

  • Alkylation
  • Amino Acid Sequence
  • Cysteine / chemistry
  • Molecular Structure
  • Peptides / chemical synthesis
  • Peptides / chemistry*
  • Sulfhydryl Compounds / chemistry

Substances

  • Peptides
  • Sulfhydryl Compounds
  • Cysteine