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Reduction of Benzoquinones to Hydroquinones via Spontaneous Reaction with Glutathione and Enzymatic Reaction by S-Glutathionyl-Hydroquinone Reductases

Lam , L.K. Metthew; Zhang, Zhicheng; Board, Philip; Xun, Luying

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S-Glutathionyl-hydroquinone reductases (GS-HQRs) are a new class of glutathione transferases, widely present in bacteria, halobacteria, fungi, and plants. They catalyze glutathione (GSH)-dependent reduction of GS-trichloro-p-hydroquinone to trichloro-p-hydroquinone. Since GS-trichloro-p-hydroquinone is uncommon in nature, the extensive presence of GS-HQRs suggests they use common GS-hydroquinones. Here we demonstrate that several benzoquinones spontaneously reacted with GSH to form...[Show more]

dc.contributor.authorLam , L.K. Metthew
dc.contributor.authorZhang, Zhicheng
dc.contributor.authorBoard, Philip
dc.contributor.authorXun, Luying
dc.date.accessioned2015-12-10T22:29:06Z
dc.identifier.issn0006-2960
dc.identifier.urihttp://hdl.handle.net/1885/54743
dc.description.abstractS-Glutathionyl-hydroquinone reductases (GS-HQRs) are a new class of glutathione transferases, widely present in bacteria, halobacteria, fungi, and plants. They catalyze glutathione (GSH)-dependent reduction of GS-trichloro-p-hydroquinone to trichloro-p-hydroquinone. Since GS-trichloro-p-hydroquinone is uncommon in nature, the extensive presence of GS-HQRs suggests they use common GS-hydroquinones. Here we demonstrate that several benzoquinones spontaneously reacted with GSH to form GS-hydroquinones via Michael addition, and four GS-HQRs from yeast and bacteria reduced the GS-hydroquinones to the corresponding hydroquinones. The spontaneous and enzymatic reactions led to the reduction of benzoquinones to hydroquinones with the concomitant oxidation of GSH to oxidized glutathione (GS-SG). The enzymes did not use GS-benzoquinones or other thiol-hydroquinones, for example, S-cysteinyl-hydroquinone, as substrates. Apparent kinetic parameters showed the enzymes preferred hydrophobic, bulky substrates, such as GS-menadiol. The broad substrate range and their wide distribution suggest two potential physiological roles: channeling GS-hydroquinones back to hydroquinones and reducing benzoquinones via spontaneous formation of GS-hydroquinones and then enzymatic reduction to hydroquinones. The functions are likely important in metabolic pathways with quinone intermediates.
dc.publisherAmerican Chemical Society
dc.sourceBiochemistry
dc.subjectKeywords: Apparent kinetic parameters; Benzoquinones; Concomitant oxidation; Enzymatic reaction; Enzymatic reduction; Glutathione transferase; Glutathiones; Metabolic pathways; Michael additions; Spontaneous formation; Spontaneous reactions; Substrate range; Additi
dc.titleReduction of Benzoquinones to Hydroquinones via Spontaneous Reaction with Glutathione and Enzymatic Reaction by S-Glutathionyl-Hydroquinone Reductases
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume51
dc.date.issued2012
local.identifier.absfor060107 - Enzymes
local.identifier.ariespublicationu4020362xPUB309
local.type.statusPublished Version
local.contributor.affiliationLam , L.K. Metthew, Washington State University
local.contributor.affiliationZhang, Zhicheng, Washington State University
local.contributor.affiliationBoard, Philip, College of Medicine, Biology and Environment, ANU
local.contributor.affiliationXun, Luying, Washington State University
local.description.embargo2037-12-31
local.bibliographicCitation.issue25
local.bibliographicCitation.startpage5014
local.bibliographicCitation.lastpage21
local.identifier.doi10.1021/bi300477z
dc.date.updated2016-02-24T10:27:51Z
local.identifier.scopusID2-s2.0-84862854753
local.identifier.thomsonID000305661800004
CollectionsANU Research Publications

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