N-Chlorosuccinimide, an efficient reagent for on-resin disulfide formation in solid-phase peptide synthesis.

Tobias M Postma, Fernando Albericio

Institute for Research in Biomedicine, Barcelona 08028, Spain.

Organic letters 2013 Feb 1

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N-Chlorosuccinimide is described as a widely applicable on-resin disulfide-forming reagent. Disulfide bond formation was completed within 15 min in DMF. This strategy was successfully used in the synthesis of oxytocin and a regioselective synthesis of an α-conotoxin. Moreover, disulfide formation with N-chlorosuccinimide was found to be compatible with oxidation-prone methionine and tryptophan.

Citation

Tobias M Postma, Fernando Albericio. N-Chlorosuccinimide, an efficient reagent for on-resin disulfide formation in solid-phase peptide synthesis. Organic letters. 2013 Feb 1;15(3):616-9