{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T21:25:56Z","timestamp":1790889956067,"version":"4.1.0"},"reference-count":40,"publisher":"National Academy of Sciences","issue":"13","license":[{"start":{"date-parts":[[2024,3,20]],"date-time":"2024-03-20T00:00:00Z","timestamp":1710892800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-19-CE44-0014-01"],"award-info":[{"award-number":["ANR-19-CE44-0014-01"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Agance nationale de la recherche","award":["ANR-11-LABX-0011"],"award-info":[{"award-number":["ANR-11-LABX-0011"]}]}],"content-domain":{"domain":["www.pnas.org"],"crossmark-restriction":true},"short-container-title":["Proc. Natl. Acad. Sci. U.S.A."],"published-print":{"date-parts":[[2024,3,26]]},"abstract":"<jats:p>\n                    All biological hydroxylation reactions are thought to derive the oxygen atom from one of three inorganic oxygen donors, O\n                    <jats:sub>2<\/jats:sub>\n                    , H\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2,<\/jats:sub>\n                    or H\n                    <jats:sub>2<\/jats:sub>\n                    O. Here, we have identified the organic compound prephenate as the oxygen donor for the three hydroxylation steps of the O\n                    <jats:sub>2<\/jats:sub>\n                    -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\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    under anaerobic conditions. Metabolic labeling experiments with\n                    <jats:sup>18<\/jats:sup>\n                    O-shikimate, a precursor of prephenate, demonstrated the incorporation of\n                    <jats:sup>18<\/jats:sup>\n                    O atoms into ubiquinone. The role of specific iron\u2013sulfur enzymes belonging to the widespread U32 protein family is discussed. Prephenate-dependent hydroxylation reactions represent a unique biochemical strategy for adaptation to anaerobic environments.\n                  <\/jats:p>","DOI":"10.1073\/pnas.2321242121","type":"journal-article","created":{"date-parts":[[2024,3,20]],"date-time":"2024-03-20T13:39:32Z","timestamp":1710941972000},"update-policy":"https:\/\/doi.org\/10.1073\/pnas.cm10313","source":"Crossref","is-referenced-by-count":9,"title":["An organic O donor for biological hydroxylation reactions"],"prefix":"10.1073","volume":"121","author":[{"given":"Katayoun Kazemzadeh","family":"Ferizhendi","sequence":"first","affiliation":[{"name":"Univ. Grenoble Alpes, CNRS, UMR 5525, VetAgro Sup, Grenoble INP, TIMC, Grenoble 38000, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philippe","family":"Simon","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie des Processus Biologiques, Institut de Chimie, Coll\u00e8ge de France, CNRS UMR 8229, PSL Research University, Sorbonne Universit\u00e9, Paris 75005, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ludovic","family":"Pelosi","sequence":"additional","affiliation":[{"name":"Univ. Grenoble Alpes, CNRS, UMR 5525, VetAgro Sup, Grenoble INP, TIMC, Grenoble 38000, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emmanuel","family":"S\u00e9chet","sequence":"additional","affiliation":[{"name":"SAMe Unit, D\u00e9partement de Microbiologie, Institut Pasteur, Universit\u00e9 Paris-Cit\u00e9, UMR CNRS 6047, Paris F-75015, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-6969-5872","authenticated-orcid":false,"given":"Roache","family":"Arulanandam","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie des Processus Biologiques, Institut de Chimie, Coll\u00e8ge de France, CNRS UMR 8229, PSL Research University, Sorbonne Universit\u00e9, Paris 75005, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3240-7548","authenticated-orcid":false,"given":"Mahmoud Hajj","family":"Chehade","sequence":"additional","affiliation":[{"name":"Univ. Grenoble Alpes, CNRS, UMR 5525, VetAgro Sup, Grenoble INP, TIMC, Grenoble 38000, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martial","family":"Rey","sequence":"additional","affiliation":[{"name":"Institut Pasteur, Universit\u00e9 Paris Cit\u00e9, CNRS UAR2024, Mass Spectrometry for Biology, Paris F-75015, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Deniz","family":"Onal","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie des Processus Biologiques, Institut de Chimie, Coll\u00e8ge de France, CNRS UMR 8229, PSL Research University, Sorbonne Universit\u00e9, Paris 75005, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Laura","family":"Flandrin","sequence":"additional","affiliation":[{"name":"Univ. Grenoble Alpes, CNRS, UMR 5525, VetAgro Sup, Grenoble INP, TIMC, Grenoble 38000, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rouba","family":"Chreim","sequence":"additional","affiliation":[{"name":"Univ. Grenoble Alpes, CNRS, UMR 5525, VetAgro Sup, Grenoble INP, TIMC, Grenoble 38000, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bruno","family":"Faivre","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie des Processus Biologiques, Institut de Chimie, Coll\u00e8ge de France, CNRS UMR 8229, PSL Research University, Sorbonne Universit\u00e9, Paris 75005, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Samuel Chau-Duy-Tam","family":"Vo","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie des Processus Biologiques, Institut de Chimie, Coll\u00e8ge de France, CNRS UMR 8229, PSL Research University, Sorbonne Universit\u00e9, Paris 75005, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5008-6437","authenticated-orcid":false,"given":"Rodrigo","family":"Arias-Cartin","sequence":"additional","affiliation":[{"name":"SAMe Unit, D\u00e9partement de Microbiologie, Institut Pasteur, Universit\u00e9 Paris-Cit\u00e9, UMR CNRS 6047, Paris F-75015, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3458-2574","authenticated-orcid":false,"given":"Fr\u00e9d\u00e9ric","family":"Barras","sequence":"additional","affiliation":[{"name":"SAMe Unit, D\u00e9partement de Microbiologie, Institut Pasteur, Universit\u00e9 Paris-Cit\u00e9, UMR CNRS 6047, Paris F-75015, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8016-4747","authenticated-orcid":false,"given":"Marc","family":"Fontecave","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie des Processus Biologiques, Institut de Chimie, Coll\u00e8ge de France, CNRS UMR 8229, PSL Research University, Sorbonne Universit\u00e9, Paris 75005, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emmanuelle","family":"Bouveret","sequence":"additional","affiliation":[{"name":"SAMe Unit, D\u00e9partement de Microbiologie, Institut Pasteur, Universit\u00e9 Paris-Cit\u00e9, UMR CNRS 6047, Paris F-75015, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4775-3494","authenticated-orcid":false,"given":"Murielle","family":"Lombard","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie des Processus Biologiques, Institut de Chimie, Coll\u00e8ge de France, CNRS UMR 8229, PSL Research University, Sorbonne Universit\u00e9, Paris 75005, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2083-3002","authenticated-orcid":false,"given":"Fabien","family":"Pierrel","sequence":"additional","affiliation":[{"name":"Univ. 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Arias-Cartin , Role of the Escherichia coli ubiquinone-synthesizing UbiUVT pathway in adaptation to changing respiratory conditions. mBio 14, e0329822 (2023).","journal-title":"mBio"},{"key":"e_1_3_4_16_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkx969"},{"key":"e_1_3_4_17_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-10750-8"},{"key":"e_1_3_4_18_2","doi-asserted-by":"publisher","DOI":"10.1128\/JB.00433-19"},{"key":"e_1_3_4_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi9926680"},{"key":"e_1_3_4_20_2","doi-asserted-by":"publisher","DOI":"10.1042\/bj1000001"},{"key":"e_1_3_4_21_2","doi-asserted-by":"publisher","DOI":"10.1105\/tpc.109.073247"},{"key":"e_1_3_4_22_2","first-page":"559","volume-title":"Methods in Enzymology","author":"Dayan J.","year":"1970","unstructured":"J. Dayan, D. B. 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