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

研究成果: Article査読

31 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)312-319
ページ数8
ジャーナルInternational Journal of Peptide and Protein Research
45
4
DOI
出版ステータスPublished - 1995 4
外部発表はい

ASJC Scopus subject areas

  • Biochemistry

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