title: Evidence that ubiquinone is a required intermediate for rhodoquinone biosynthesis in Rhodospirillum rubrum.
abstract: Rhodoquinone (RQ) is an important cofactor used in the anaerobic energy metabolism of Rhodospirillum rubrum. RQ is structurally similar to ubiquinone (coenzyme Q or Q), a polyprenylated benzoquinone used in the aerobic respiratory chain. RQ is also found in several eukaryotic species that utilize a fumarate reductase pathway for anaerobic respiration, an important example being the parasitic helminths. RQ is not found in humans or other mammals, and therefore inhibition of its biosynthesis may provide a parasite-specific drug target. In this report, we describe several in vivo feeding experiments with R. rubrum used for the identification of RQ biosynthetic intermediates. Cultures of R. rubrum were grown in the presence of synthetic analogs of ubiquinone and the known Q biosynthetic precursors demethylubiquinone, demethoxyubiquinone, and demethyldemethoxyubiquinone, and assays were monitored for the formation of RQ(3). Data from time course experiments and S-adenosyl-l-methionine-dependent O-methyltransferase inhibition studies are discussed. Based on the results presented, we have demonstrated that Q is a required intermediate for the biosynthesis of RQ in R. rubrum.
authors.affiliation: Department of Chemistry and Biochemistry, Gonzaga University, Spokane, WA 99258-0005, USA.
authors.forename: Brian C
authors.initials: BC
authors.lastname: Brajcich
authors.forename: Andrew L
authors.initials: AL
authors.lastname: Iarocci
authors.forename: Lindsey A G
authors.initials: LA
authors.lastname: Johnstone
authors.forename: Rory K
authors.initials: RK
authors.lastname: Morgan
authors.forename: Zachary T
authors.initials: ZT
authors.lastname: Lonjers
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Hotchko
authors.forename: Jordan D
authors.initials: JD
authors.lastname: Muhs
authors.forename: Amanda
authors.initials: A
authors.lastname: Kieffer
authors.forename: Bree J
authors.initials: BJ
authors.lastname: Reynolds
authors.forename: Sarah M
authors.initials: SM
authors.lastname: Mandel
authors.forename: Beth N
authors.initials: BN
authors.lastname: Marbois
authors.forename: Catherine F
authors.initials: CF
authors.lastname: Clarke
authors.forename: Jennifer N
authors.initials: JN
authors.lastname: Shepherd
mesh_terms: D002853:Chromatography, Liquid; D013058:Mass Spectrometry; D008954:Models, Biological; D015394:Molecular Structure; D012247:Rhodospirillum rubrum / Q000378:metabolism*; D014451:Ubiquinone / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry / Q000378:metabolism*
chemical_list: D014451:Ubiquinone; C003304:rhodoquinone