Journal
TETRAHEDRON
Volume 66, Issue 17, Pages 3228-3241Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.02.077
Keywords
1-Chlorobenzotriazole; Unsymmetrical disulfide; Cystine
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Funding
- South African National Research Foundation
- University of Cape Town
- Claude-Leon Foundation
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A high-yielding and low temperature one-pot procedure is described for unsymmetrical disulfide synthesis from two different thiols using 1-chlorobenzotriazole (BtCl) as oxidant. The mechanism of the coupling involves in situ trapping of the sulfenyl chloride intermediate R(1)SCl by nucleophilic benzotriazole (BtH) to form R(1)SBt, which protects R(1)SCl from forming the homodimer R(1)SSR(1). The methodology is applicable to all types of thiol (aliphatic, aromatic, heteroaromatic), with a variation developed for aliphatic-aliphatic couplings. Differentially N-protected cysteines couple to afford the unsymmetrical cystine derivatives in high yield (90%), which serves as a model for the one-pot intermolecular coupling of cysteine-containing peptides to form peptide disulfide heterodimers. Minimal exchange in aromatic-aromatic disulfide synthesis is noted on account of the mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.
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