Investigation of the Dimethylsulfoxide-Trifluoroacetic Acid Oxidation System for the Synthesis of Cystine-Containing Peptides

Takaki Koide; Akira Otaka; Nobutaka Fujii

doi:10.1248/cpb.41.1030

Investigation of the Dimethylsulfoxide-Trifluoroacetic Acid Oxidation System for the Synthesis of Cystine-Containing Peptides

Takaki Koide, Akira Otaka, Nobutaka Fujii

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

20 Citations (Scopus)

Abstract

Disulfide bonds of peptides were effectively established between S-protected cysteine residues as well as free cysteine residues by the action of dimethylsulfoxide in trifluoroacetic acid. Oxytocin and a-human calcitonin gene-related peptide were synthesized using this oxidation system. The feasibility of this method for the formation of two disulfide bridges of apamin was also examined.

Original language	English
Pages (from-to)	1030-1034
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	41
Issue number	6
DOIs	https://doi.org/10.1248/cpb.41.1030
Publication status	Published - 1993
Externally published	Yes

Keywords

Keywords cystine-containing peptide
apamin
calcitonin gene-related peptide
dimethylsulfoxide
disulfide bond-formation
oxytocin

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.41.1030

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abstract = "Disulfide bonds of peptides were effectively established between S-protected cysteine residues as well as free cysteine residues by the action of dimethylsulfoxide in trifluoroacetic acid. Oxytocin and a-human calcitonin gene-related peptide were synthesized using this oxidation system. The feasibility of this method for the formation of two disulfide bridges of apamin was also examined.",

keywords = "Keywords cystine-containing peptide, apamin, calcitonin gene-related peptide, dimethylsulfoxide, disulfide bond-formation, oxytocin",

author = "Takaki Koide and Akira Otaka and Nobutaka Fujii",

year = "1993",

doi = "10.1248/cpb.41.1030",

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T1 - Investigation of the Dimethylsulfoxide-Trifluoroacetic Acid Oxidation System for the Synthesis of Cystine-Containing Peptides

AU - Koide, Takaki

AU - Otaka, Akira

AU - Fujii, Nobutaka

PY - 1993

Y1 - 1993

N2 - Disulfide bonds of peptides were effectively established between S-protected cysteine residues as well as free cysteine residues by the action of dimethylsulfoxide in trifluoroacetic acid. Oxytocin and a-human calcitonin gene-related peptide were synthesized using this oxidation system. The feasibility of this method for the formation of two disulfide bridges of apamin was also examined.

AB - Disulfide bonds of peptides were effectively established between S-protected cysteine residues as well as free cysteine residues by the action of dimethylsulfoxide in trifluoroacetic acid. Oxytocin and a-human calcitonin gene-related peptide were synthesized using this oxidation system. The feasibility of this method for the formation of two disulfide bridges of apamin was also examined.

KW - Keywords cystine-containing peptide

KW - apamin

KW - calcitonin gene-related peptide

KW - dimethylsulfoxide

KW - disulfide bond-formation

KW - oxytocin

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DO - 10.1248/cpb.41.1030

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Investigation of the Dimethylsulfoxide-Trifluoroacetic Acid Oxidation System for the Synthesis of Cystine-Containing Peptides

Abstract

Keywords

ASJC Scopus subject areas

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