Investigation of the dimethylsulfoxide-trifluoroacetic acid oxidation system for the synthesis of cystine-containing peptides

Takaki Koide, A. Otaka, N. Fujii

Research output: Contribution to journalArticle

18 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 α-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 languageEnglish
Pages (from-to)1030-1034
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number6
Publication statusPublished - 1993
Externally publishedYes

Fingerprint

Trifluoroacetic Acid
Cystine
Dimethyl Sulfoxide
Disulfides
Cysteine
Apamin
Oxidation
Peptides
Calcitonin Gene-Related Peptide
Oxytocin

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Investigation of the dimethylsulfoxide-trifluoroacetic acid oxidation system for the synthesis of cystine-containing peptides. / Koide, Takaki; Otaka, A.; Fujii, N.

In: Chemical and Pharmaceutical Bulletin, Vol. 41, No. 6, 1993, p. 1030-1034.

Research output: Contribution to journalArticle

@article{195c687caf904b56b33e7edab647020b,
title = "Investigation of the dimethylsulfoxide-trifluoroacetic acid oxidation system for the synthesis of cystine-containing peptides",
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 α-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.",
author = "Takaki Koide and A. Otaka and N. Fujii",
year = "1993",
language = "English",
volume = "41",
pages = "1030--1034",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
number = "6",

}

TY - JOUR

T1 - Investigation of the dimethylsulfoxide-trifluoroacetic acid oxidation system for the synthesis of cystine-containing peptides

AU - Koide, Takaki

AU - Otaka, A.

AU - Fujii, N.

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 α-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 α-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.

UR - http://www.scopus.com/inward/record.url?scp=0027237565&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027237565&partnerID=8YFLogxK

M3 - Article

VL - 41

SP - 1030

EP - 1034

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 6

ER -