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

Research output: Contribution to journalArticle

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
Externally publishedYes

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Cystine
Hydrochloric Acid
Oxytocin
Dimethyl Sulfoxide
Disulfides
Cysteine
Amino Acids
Oxidation
Peptides
urotensin II
(S-acetamidomethyl)cysteine
trifluoromethanesulfonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Disulfide bond formation in S-Acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide / aqueous HCl. / Tamamura, Hirokazu; Otaka, Akira; Nakamura, Junko; Okubo, Kaori; Koide, Takaki; Ikeda, Kyoko; Fujii, Nobutaka.

In: Tetrahedron Letters, Vol. 34, No. 31, 30.07.1993, p. 4931-4934.

Research output: Contribution to journalArticle

Tamamura, Hirokazu ; Otaka, Akira ; Nakamura, Junko ; Okubo, Kaori ; Koide, Takaki ; Ikeda, Kyoko ; Fujii, Nobutaka. / Disulfide bond formation in S-Acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide / aqueous HCl. In: Tetrahedron Letters. 1993 ; Vol. 34, No. 31. pp. 4931-4934.
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AU - Ikeda, Kyoko

AU - Fujii, Nobutaka

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