N-Chlorosuccinimide, an Efficient Reagent for On-Resin Disulfide Formation in Solid-Phase Peptide Synthesis | Zendy

Tobias M. Postma | Zendy; Fernando Alberício | Zendy

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N-Chlorosuccinimide, an Efficient Reagent for On-Resin Disulfide Formation in Solid-Phase Peptide Synthesis

Author(s) -

Tobias M. Postma,

Fernando Alberício

Publication year - 2013

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol303428d

Subject(s) - chemistry , disulfide bond , reagent , regioselectivity , solid phase synthesis , peptide synthesis , methionine , combinatorial chemistry , tryptophan , organic chemistry , peptide , amino acid , catalysis , biochemistry

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.

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