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

doi:10.1016/S0040-4039(00)74049-4

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

研究成果: Article

28 引用（Scopus）

抜粋

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.

元の言語	English
ページ（範囲）	4931-4934
ページ数	4
ジャーナル	Tetrahedron Letters
巻	34
発行部数	31
DOI	https://doi.org/10.1016/S0040-4039(00)74049-4
出版物ステータス	Published - 1993 7 30
外部発表	Yes

フィンガープリント

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

これを引用

Tamamura, H., Otaka, A., Nakamura, J., Okubo, K., Koide, T., Ikeda, K., & Fujii, N. (1993). Disulfide bond formation in S-Acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide / aqueous HCl. Tetrahedron Letters, 34(31), 4931-4934. https://doi.org/10.1016/S0040-4039(00)74049-4

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.

：: Tetrahedron Letters, 巻 34, 番号 31, 30.07.1993, p. 4931-4934.

研究成果: Article

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AU - Koide, Takaki

AU - Ikeda, Kyoko

AU - Fujii, Nobutaka

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文献にアクセス

10.1016/S0040-4039(00)74049-4