Disulfide bond‐forming reaction using a dimethyl sulfoxide/aqueous HCl system and its application to regioselective two disulfide bond formation

HIROKAZU TAMAMURA, AKIRA OTAKA, JUNKO NAKAMURA, KAORI OKUBO, TAKAKI KOIDE, KYOKO IKEDA, TOSHIRO IBLKA, NOBCTAKA FUJII

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Disulfide bond formation in S‐acetamidomethyl (Acm) cysteine‐containing peptides by successive treatments with silver trifluoromethanesulfonate (AgOTf) and dimethyl sulfoxide (DMSO)/aqueous HCl is described. An S‐Acm cysteine was found to be quantitatively converted into cystine by deprotection of the Acm group with AgOTf followed by DMSO/aqueous HCl treatment. Under these reaction conditions, no significant side reactions were observed with oxidation‐sensitive amino acids such as Met, Tyr and Trp. Oxytocin and a Trp‐containing peptide, urotensin II, were prepared by this method. Furthermore, regioselective two disulfide bond formation was found to be feasible by the combination of air oxidation and the AgOTf‐DMSO/HCl system. This strategy has been successfully applied to the syntheses of tachyplesin I and endothelin I, which have two disulfide bonds and a Trp residue in the molecule.

Original languageEnglish
Pages (from-to)312-319
Number of pages8
JournalInternational Journal of Peptide and Protein Research
Volume45
Issue number4
DOIs
Publication statusPublished - 1995 Apr

Keywords

  • HCI
  • S‐acetamidomethyl cysteine
  • dimethyl sulfoxide
  • endothelin I
  • regioselective disulfide bond formation
  • silver trifluoromethanesulfonate
  • tachyplesin I

ASJC Scopus subject areas

  • Biochemistry

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