Abstract

A 22-residue cyclic peptide with a 56-atom (18-residue) intramolecular disulfide has been synthesized on solid phase. Two synthetic schemes, based on Boc/benzyl chemistry and either acetamidomethyl (Acm) or 9-fluorenylmethyl (Fm) groups for cysteine protection, have been compared. The deprotection-oxidation of both S-protecting groups has been explored under several experimental conditions. The most successful route involved on-the-resin disulfide formation via Cys(Fm) deprotection-oxidation.

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