Disulfide bond‐forming reaction using a dimethyl sulfoxide/aqueous HCl system and its application to regioselective two disulfide bond formation
- 1 April 1995
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 45 (4) , 312-319
- https://doi.org/10.1111/j.1399-3011.1995.tb01043.x
Abstract
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.Keywords
This publication has 24 references indexed in Scilit:
- Acceleration of the N.ALPHA.-Deprotection Rate by the Addition of m-Cresol to Diluted Methanesulfonic Acid and Its Application to the Z(OMe)-Based Solid-Phase Syntheses of Human Pancreastatin-29 and Magainin 1.CHEMICAL & PHARMACEUTICAL BULLETIN, 1993
- Disulfide bond formation using the silyl chloride-sulfoxide system for the synthesis of a cystine peptideJournal of the American Chemical Society, 1992
- Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and applicationsJournal of the American Chemical Society, 1991
- Studies on peptides. CLXVIII. Syntheses of three peptides isolated from horseshoe crab hemocytes, tachyplesin I, tachyplesin II, and polyphemusin I.CHEMICAL & PHARMACEUTICAL BULLETIN, 1989
- Synthesis and disulfide structure determination of porcine endothelin: an endothelium‐derived vasoconstricting peptideInternational Journal of Peptide and Protein Research, 1988
- Studies on peptides. CLV. Evaluation of trimethylsilyl bromide as a hard-acid deprotecting reagent in peptide synthesis.CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
- New method of linking tryptophan to cysteine sulphydryl groups in peptides and proteinsJournal of the Chemical Society, Chemical Communications, 1976
- On Cysteine and Cystine Peptides. I. New S-Protecting Groups for CysteineJournal of the American Chemical Society, 1962
- The Synthesis of Oxytocin1Journal of the American Chemical Society, 1954
- THE SYNTHESIS OF AN OCTAPEPTIDE AMIDE WITH THE HORMONAL ACTIVITY OF OXYTOCINJournal of the American Chemical Society, 1953