Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containlng peptides in aqueous medium

Hoi Yan Shiu, Tak Chung Chan, Chi Ming Ho, Yungen Liu, Man Kin Wong, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

67 Citations (Scopus)

Abstract

An efficient method has been developed for the chemoselective cysteine modification of unprotected peptides and proteins in aqueous media through the formation of a vinyl sulfide linkage by using electron-deficient alkynes, including alkynoic amides, esters and alkynones. The terminal alkynone-modified peptides could be converted back into the unmodified peptides (81 % isolated yield) by adding thiols under mild conditions. The usefulness of this thiol-assisted cleavage of the vinyl sulfide linkage in peptides has been exemplified by the enrichment of a cysteine-containing peptide (71% recovery) from a mixture of cysteine-containing and non-cysteine-containing peptides. KGaA.
Original languageEnglish
Pages (from-to)3839-3850
Number of pages12
JournalChemistry - A European Journal
Volume15
Issue number15
DOIs
Publication statusPublished - 6 Apr 2009
Externally publishedYes

Keywords

  • Alkynes
  • Chemoselectivity
  • Cleavage reactions
  • Cysteine
  • Peptides

ASJC Scopus subject areas

  • Chemistry(all)

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