Studies on peptides CLVIII. Model experiments for the synthesis of open-chain unsymmetrical cystine-peptides

N Fujii; A Otaka; S Funakoshi; T Watanabe; H Arai; K Bessho; H Yajima

doi:10.1007/BF01025244

Studies on peptides CLVIII. Model experiments for the synthesis of open-chain unsymmetrical cystine-peptides

J Protein Chem. 1988 Apr;7(2):151-6. doi: 10.1007/BF01025244.

Authors

N Fujii¹, A Otaka, S Funakoshi, T Watanabe, H Arai, K Bessho, H Yajima

Affiliation

¹ Faculty of Pharmaceutical Sciences, Kyoto University, Japan.

PMID: 3255366
DOI: 10.1007/BF01025244

Abstract

Treatment of a mixture of Cys(R)(O) and Cys(R') with an acid was found to generate cystine in fairly good yields, when suitable R, R', and an acid were selected. An unsymmetrical cystine peptide was prepared by treatment of a mixture of Z(OMe)-Cys(R) (0)-Ala-NH2 (R = Acm or MBzl) and Z(OMe)-Cys(MBzl)-Gly-OBzl with TFA or 1 M TFMSA/TFA3. Oxytocin was obtained in an excellent yield by TFA treatment of the protected peptide containing Cys(Acm)(0) and Cys(MBzl). Thus, formation of the disulfide bond was found feasible at the position of Cys(R) (0).

MeSH terms

Cystine*
Disulfides
In Vitro Techniques
Models, Chemical*
Peptides / chemical synthesis*

Substances

Disulfides
Peptides
Cystine