Disulfide bond formation in S-Acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide / aqueous HCl

Hirokazu Tamamura, Akira Otaka, Junko Nakamura, Kaori Okubo, Takaki Koide, Kyoko Ikeda, Nobutaka Fujii

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28 Citations (Scopus)

Abstract

S-Acetamidomethyl (Acm) cysteine was found to be converted quantitatively to cystine by deprotection of the Acm group with silver trifluoromethanesulfonate (AgOTf) followed by dimethylsulfoxide (DMSO) / aqueous hydrochloric acid (HCl) treatment. No significant side reactions were observed with oxidation-sensitive amino acids such as Met, Tyr, and Trp under these reaction conditions. This method has been applied successfully to the syntheses of oxytocin and a Trp-containing peptide, urotensin II.

Original languageEnglish
Pages (from-to)4931-4934
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number31
DOIs
Publication statusPublished - 1993 Jul 30

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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