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

H. Tamamura, A. Otaka, J. Nakamura, K. Okubo, Takaki Koide, K. Ikeda, T. Ibuka, N. Fujii

Research output: Contribution to journalArticle

28 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
Publication statusPublished - 1995
Externally publishedYes

Fingerprint

Dimethyl Sulfoxide
Disulfides
Cysteine
Oxidation
Peptides
Cystine
Endothelins
Oxytocin
Air
Amino Acids
Molecules

Keywords

  • Dimethyl sulfoxide
  • Endothelin I
  • HCl
  • Regioselective disulfide bond formation
  • S-acetamidomethyl cysteine
  • Silver trifluoromethanesulfonate
  • Tachyplesin I

ASJC Scopus subject areas

  • Biochemistry

Cite this

Disulfide bond-forming reaction using a dimethyl sulfoxide/aqueous HCl system and its application to regioselective two disulfide bond formation. / Tamamura, H.; Otaka, A.; Nakamura, J.; Okubo, K.; Koide, Takaki; Ikeda, K.; Ibuka, T.; Fujii, N.

In: International Journal of Peptide and Protein Research, Vol. 45, No. 4, 1995, p. 312-319.

Research output: Contribution to journalArticle

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AU - Otaka, A.

AU - Nakamura, J.

AU - Okubo, K.

AU - Koide, Takaki

AU - Ikeda, K.

AU - Ibuka, T.

AU - Fujii, N.

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