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- Name help_outline 2-methoxy-6-(all-trans-octaprenyl)phenol Identifier CHEBI:1235 Charge 0 Formula C47H72O2 InChIKeyhelp_outline MARGKPIMNMASKJ-CMAXTTDKSA-N SMILEShelp_outline OC1=C(C\C=C(\CC\C=C(\CC\C=C(\CC\C=C(\CC\C=C(\CC\C=C(\CC\C=C(\CCC=C(C)C)/C)/C)/C)/C)/C)/C)/C)C=CC=C1OC 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline prephenate Identifier CHEBI:29934 Charge -2 Formula C10H8O6 InChIKeyhelp_outline FPWMCUPFBRFMLH-XGAOUMNUSA-L SMILEShelp_outline O[C@H]1C=C[C@](CC(=O)C([O-])=O)(C=C1)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 14 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 2,937 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,717 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 2-methoxy-6-(all-trans-octaprenyl)benzene-1,4-diol Identifier CHEBI:60655 Charge 0 Formula C47H72O3 InChIKeyhelp_outline CZFRMASEEPTBAQ-MYCGWMCTSA-N SMILEShelp_outline COc1cc(O)cc(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)c1O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 3-phenylpyruvate Identifier CHEBI:18005 (Beilstein: 3944391) help_outline Charge -1 Formula C9H7O3 InChIKeyhelp_outline BTNMPGBKDVTSJY-UHFFFAOYSA-M SMILEShelp_outline [O-]C(=O)C(=O)Cc1ccccc1 2D coordinates Mol file for the small molecule Search links Involved in 33 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 2,865 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CO2 Identifier CHEBI:16526 (CAS: 124-38-9) help_outline Charge 0 Formula CO2 InChIKeyhelp_outline CURLTUGMZLYLDI-UHFFFAOYSA-N SMILEShelp_outline O=C=O 2D coordinates Mol file for the small molecule Search links Involved in 1,032 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:81683 | RHEA:81684 | RHEA:81685 | RHEA:81686 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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An organic O donor for biological hydroxylation reactions.
Ferizhendi K.K., Simon P., Pelosi L., Sechet E., Arulanandam R., Chehade M.H., Rey M., Onal D., Flandrin L., Chreim R., Faivre B., Vo S.C., Arias-Cartin R., Barras F., Fontecave M., Bouveret E., Lombard M., Pierrel F.
All biological hydroxylation reactions are thought to derive the oxygen atom from one of three inorganic oxygen donors, O<sub>2</sub>, H<sub>2</sub>O<sub>2,</sub> or H<sub>2</sub>O. Here, we have identified the organic compound prephenate as the oxygen donor for the three hydroxylation steps of th ... >> More
All biological hydroxylation reactions are thought to derive the oxygen atom from one of three inorganic oxygen donors, O<sub>2</sub>, H<sub>2</sub>O<sub>2,</sub> or H<sub>2</sub>O. Here, we have identified the organic compound prephenate as the oxygen donor for the three hydroxylation steps of the O<sub>2</sub>-independent biosynthetic pathway of ubiquinone, a widely distributed lipid coenzyme. Prephenate is an intermediate in the aromatic amino acid pathway and genetic experiments showed that it is essential for ubiquinone biosynthesis in <i>Escherichia coli</i> under anaerobic conditions. Metabolic labeling experiments with <sup>18</sup>O-shikimate, a precursor of prephenate, demonstrated the incorporation of <sup>18</sup>O atoms into ubiquinone. The role of specific iron-sulfur enzymes belonging to the widespread U32 protein family is discussed. Prephenate-dependent hydroxylation reactions represent a unique biochemical strategy for adaptation to anaerobic environments. << Less
Proc Natl Acad Sci U S A 121:e2321242121-e2321242121(2024) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.
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Ubiquinone biosynthesis over the entire O2 range: characterization of a conserved O2-independent pathway.
Pelosi L., Vo C.D., Abby S.S., Loiseau L., Rascalou B., Hajj Chehade M., Faivre B., Gousse M., Chenal C., Touati N., Binet L., Cornu D., Fyfe C.D., Fontecave M., Barras F., Lombard M., Pierrel F.
Most bacteria can generate ATP by respiratory metabolism, in which electrons are shuttled from reduced substrates to terminal electron acceptors, via quinone molecules like ubiquinone. Dioxygen (O<sub>2</sub>) is the terminal electron acceptor of aerobic respiration and serves as a co-substrate in ... >> More
Most bacteria can generate ATP by respiratory metabolism, in which electrons are shuttled from reduced substrates to terminal electron acceptors, via quinone molecules like ubiquinone. Dioxygen (O<sub>2</sub>) is the terminal electron acceptor of aerobic respiration and serves as a co-substrate in the biosynthesis of ubiquinone. Here, we characterize a novel, O<sub>2</sub>-independent pathway for the biosynthesis of ubiquinone. This pathway relies on three proteins, UbiT (YhbT), UbiU (YhbU), and UbiV (YhbV). UbiT contains an SCP2 lipid-binding domain and is likely an accessory factor of the biosynthetic pathway, while UbiU and UbiV (UbiU-UbiV) are involved in hydroxylation reactions and represent a novel class of O<sub>2</sub>-independent hydroxylases. We demonstrate that UbiU-UbiV form a heterodimer, wherein each protein binds a 4Fe-4S cluster via conserved cysteines that are essential for activity. The UbiT, -U, and -V proteins are found in alpha-, beta-, and gammaproteobacterial clades, including several human pathogens, supporting the widespread distribution of a previously unrecognized capacity to synthesize ubiquinone in the absence of O<sub>2</sub> Together, the O<sub>2</sub>-dependent and O<sub>2</sub>-independent ubiquinone biosynthesis pathways contribute to optimizing bacterial metabolism over the entire O<sub>2</sub> range.<b>IMPORTANCE</b> In order to colonize environments with large O<sub>2</sub> gradients or fluctuating O<sub>2</sub> levels, bacteria have developed metabolic responses that remain incompletely understood. Such adaptations have been recently linked to antibiotic resistance, virulence, and the capacity to develop in complex ecosystems like the microbiota. Here, we identify a novel pathway for the biosynthesis of ubiquinone, a molecule with a key role in cellular bioenergetics. We link three uncharacterized genes of <i>Escherichia coli</i> to this pathway and show that the pathway functions independently from O<sub>2</sub> In contrast, the long-described pathway for ubiquinone biosynthesis requires O<sub>2</sub> as a substrate. In fact, we find that many proteobacteria are equipped with the O<sub>2</sub>-dependent and O<sub>2</sub>-independent pathways, supporting that they are able to synthesize ubiquinone over the entire O<sub>2</sub> range. Overall, we propose that the novel O<sub>2</sub>-independent pathway is part of the metabolic plasticity developed by proteobacteria to face various environmental O<sub>2</sub> levels. << Less
MBio 10:E01319-E01319(2019) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.