Collect. Czech. Chem. Commun. 1988, 53, 2537-2541

Formation of open-chain asymmetrical cystine peptides on a solid support. Synthesis of pGlu-Asn-Cyt-Pro-Arg-Gly-OH

Paul B. W. Ten Kortenaar and Jan W. Van Nispen

Organon Scientific Development Group, P.O. Box 20, 5340 BH Oss, The Netherlands


The feasibility of the synthesis of assymetric disulfide-containing peptides on solid phase resins was investigated. Using a fragment of [8-arginine]vasopressin as a model, the conversion of the S-acetamidomethylcysteine-containing peptide-resin into the corresponding S-carboxymethylsulfenyl derivative followed by reaction with free cysteine was studied. Both reactions proceeded smoothly under mild conditions. After cleavage from the resin the peptide was shown to have the correct composition.