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. 2014 Sep 18;14:675. doi: 10.1186/1471-2407-14-675

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© McGoldrick et al.; licensee BioMed Central Ltd. 2014

This article is published under license to BioMed Central Ltd. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly credited. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.

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Mechanism of N-acetylalaninate prodrug activation by OPH and subsequent depletion of glutathione. A) The ester bond of the prodrug is cleaved by the esterase activity of oxidized protein hydrolase (OPH) releasing acetylalaninate (Ac-Ala) and a (4-hydroxyphenyl)methyl nitrate intermediate. B) The intermediate quickly undergoes elimination releasing NO₃ ^- and forming a reactive quinone methide (QM). C) The QM rapidly reacts with the thiol group of reduced glutathione (GSH) in a Michael addition leaving GSH unavailable to participate in cellular redox reactions.