On-resin conversion of Cys(Acm)-containing peptides to their corresponding Cys(Scm) congeners

Daniel G. Mullen, Benjamin Weigel, George Barany, Mark D. Distefano

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The Acm protecting group for the thiol functionality of cysteine is removed under conditions (Hg2+) that are orthogonal to the acidic milieu used for global deprotection in Fmoc-based solid-phase peptide synthesis. This use of a toxic heavy metal for deprotection has limited the usefulness of Acm in peptide synthesis. The Acm group may be converted to the Scm derivative that can then be used as a reactive intermediate for unsymmetrical disulfide formation. It may also be removed by mild reductive conditions to generate unprotected cysteine. Conversion of Cys(Acm)-containing peptides to their corresponding Cys(Scm) derivatives in solution is often problematic because the sulfenyl chloride reagent used for this conversion may react with the sensitive amino acids tyrosine and tryptophan. In this protocol, we report a method for on-resin Acm to Scm conversion that allows the preparation of Cys(Scm)-containing peptides under conditions that do not modify other amino acids.

Original languageEnglish (US)
Pages (from-to)219-222
Number of pages4
JournalJournal of Peptide Science
Volume16
Issue number5
DOIs
StatePublished - May 2010

Keywords

  • Acetamidomethyl
  • Cys(Acm)
  • Cys(Scm)
  • Methoxycarbonylsulfenyl chloride
  • On-resin conversion
  • S-carbomethoxysulfenyl
  • SPPS

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