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American Chemical Society, Organic Letters, 17(17), p. 4196-4199, 2015

DOI: 10.1021/acs.orglett.5b01962

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Diallyl Trisulfide Is a Fast H2S Donor, but Diallyl Disulfide Is a Slow One: The Reaction Pathways and Intermediates of Glutathione with Polysulfides

Journal article published in 2015 by Dong Liang, Haixia Wu, Ming Wah Wong, Dejian Huang
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Diallyl trisulfide (DATS) reacts rapidly with glutathione (GSH) to release H2S through thiol-disulfide exchange followed by allyl perthiol reduction by GSH. Yet diallyl disulfide (DADS) only releases a minute amount of H2S via a sluggish reaction with GSH through an α-carbon nucleophilic substitution pathway. The results clarify the misunderstanding of DADS as a rapid H2S donor, which is attributed to its DATS impurity.