title: N-Chlorosuccinimide, an efficient reagent for on-resin disulfide formation in solid-phase peptide synthesis.
abstract: 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.
authors: Institute for Research in Biomedicine, Barcelona 08028, Spain.
authors: Tobias M
authors: TM
authors: Postma
authors: Fernando
authors: F
authors: Albericio
mesh_terms: D020916:Conotoxins / Q000138:chemical synthesis; D004220:Disulfides / Q000737:chemistry*; D007202:Indicators and Reagents; D008715:Methionine / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011108:Polymers / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D013388:Succinimides / Q000737:chemistry*; D014364:Tryptophan / Q000737:chemistry
chemical_list: D020916:Conotoxins; D004220:Disulfides; D007202:Indicators and Reagents; D011108:Polymers; D013388:Succinimides; C015752:N-chlorosuccinimide; D014364:Tryptophan; D008715:Methionine