Serine/Threonine Ligation and Cysteine/Penicillamine Ligation

Methods Mol Biol. 2022:2530:33-43. doi: 10.1007/978-1-0716-2489-0_3.

Abstract

Serine/threonine ligation (STL) and cysteine/penicillamine ligation (CPL) are highly chemo- and regioselective reactions between unprotected peptides with C-terminus salicylaldehyde esters and unprotected peptides with N-terminus serine/threonine or cysteine/penicillamine, which serve as powerful tools for cyclic peptide natural product and chemical protein synthesis. Herein, we introduce the preparation of C-terminal peptide salicylaldehyde esters, serine/threonine ligation, cysteine/penicillamine ligation, and subsequent acidolysis.

Keywords: Acidolysis; Chemical protein synthesis; Cyclic peptide; Cysteine/penicillamine ligation; Peptide salicylaldehyde ester; Serine/threonine ligation.

MeSH terms

  • Cysteine
  • Esters
  • Penicillamine
  • Peptides
  • Serine*
  • Threonine*

Substances

  • Esters
  • Peptides
  • Threonine
  • Serine
  • Penicillamine
  • Cysteine