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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The kinetics and mechanism of the oxidation of mercaptoethanol by riboflavin

JW Holden and L Main

Australian Journal of Chemistry 30(6) 1387 - 1391
Published: 1977

Abstract

Kinetic study of the oxidation of mercaptoethanol (RSH) by riboflavin (FlH) over the pH range 8.5-10.5 establishes that the rate is given by the term 0.036[FlH][RSH][RS-]]2 mol-2 s-1, there being no buffer catalysis. Any reactivity of the N 3-ionized riboflavin species (Fl-) is sufficiently low to be kinetically undetected. The kinetic form and lack of general acid catalysis are consistent with a nucleophilic (thiolate) 4a-addition-elimination mechanism previously proposed, but a possible alternative mechanism involving a flavin semiquinone (radical) intermediate is suggested.

https://doi.org/10.1071/CH9771387

© CSIRO 1977

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