Selective desulfurization of cysteine in the presence of Cys(Acm) in polypeptides obtained by native chemical ligation

Org Lett. 2007 Feb 15;9(4):687-90. doi: 10.1021/ol0630144.

Abstract

Increased versatility for the synthesis of proteins and peptides by native chemical ligation requires the ability to ligate at positions other than Cys. Here, we report that Raney nickel can be used under standard conditions for the selective desulfurization of Cys in the presence of Cys(Acm). This simple and practical tactic enables the more common Xaa-Ala junctions to be used as ligation sites for the chemical synthesis of Cys-containing peptides and proteins. [reaction: see text].

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Amyloid / chemical synthesis
  • Cysteine / analogs & derivatives*
  • Cysteine / chemistry*
  • Islet Amyloid Polypeptide
  • Models, Molecular
  • Molecular Sequence Data
  • Peptides / chemical synthesis*
  • Spectrometry, Mass, Electrospray Ionization
  • Sulfur / chemistry*

Substances

  • Amyloid
  • Islet Amyloid Polypeptide
  • Peptides
  • Sulfur
  • Cysteine