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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

31 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 language	English
Pages (from-to)	4931-4934
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(00)74049-4
Publication status	Published - 1993 Jul 30
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)74049-4

Cite this

@article{8ad5772eddfe4bc3ba94784ae314cdbe,

title = "Disulfide bond formation in S-Acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide / aqueous HCl",

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.",

author = "Hirokazu Tamamura and Akira Otaka and Junko Nakamura and Kaori Okubo and Takaki Koide and Kyoko Ikeda and Nobutaka Fujii",

year = "1993",

month = jul,

day = "30",

doi = "10.1016/S0040-4039(00)74049-4",

language = "English",

volume = "34",

pages = "4931--4934",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "31",

}

TY - JOUR

T1 - Disulfide bond formation in S-Acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide / aqueous HCl

AU - Tamamura, Hirokazu

AU - Otaka, Akira

AU - Nakamura, Junko

AU - Okubo, Kaori

AU - Koide, Takaki

AU - Ikeda, Kyoko

AU - Fujii, Nobutaka

PY - 1993/7/30

Y1 - 1993/7/30

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0027293130&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027293130&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)74049-4

DO - 10.1016/S0040-4039(00)74049-4

M3 - Article

AN - SCOPUS:0027293130

SN - 0040-4039

VL - 34

SP - 4931

EP - 4934

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Disulfide bond formation in S-Acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide / aqueous HCl

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this