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Biosynthesis of DHN\u2010derived metabolites requires precise spatial control of radical reactions to form specific C\u2500C or C\u2500O\u2500C bonds. Investigating fungal PQ biosynthesis in\n                    <jats:italic>Alternaria alternata<\/jats:italic>\n                    , we identified a cytochrome P450 enzyme that catalyzes a highly regio\u2010 and stereospecific C\u2500C radical coupling reaction. Conversely, a DHN\u2010converting P450 from\n                    <jats:italic>Berkleasmium<\/jats:italic>\n                    sp. utilizes a diradical mechanism yielding a C\u2500O\u2500C bridge. Comparing these enzymes revealed five sequence motifs that, with structural modeling, allowed the identification of a novel\n                    <jats:italic>A. alternata<\/jats:italic>\n                    enzyme converting 1,8\u2010DHN to a 2\u20102' DHN dimer. We demonstrate that P450\u2010dependent PQ biosynthesis in\n                    <jats:italic>A. alternata<\/jats:italic>\n                    is fundamentally distinct from the laccase\u2010fasciclin\u2010mediated pathway in\n                    <jats:italic>Cercospora beticola<\/jats:italic>\n                    , indicating that PQ biosynthesis evolved via distinct, lineage\u2010specific pathways through convergent evolution. Finally, PQs contribute to microbial niche shaping on tomato fruits. Understanding these pathways provides a foundation for producing PQs for medical applications.\n                  <\/jats:p>","DOI":"10.1002\/anie.2505284","type":"journal-article","created":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T08:08:04Z","timestamp":1789718884000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Intermolecular Carbon\u2013Carbon Naphthalene Coupling Involves a Radical Mechanism Driven by Cytochrome P450 in\n                    <i>Alternaria alternata<\/i>"],"prefix":"10.1002","author":[{"given":"Jia","family":"Gao","sequence":"first","affiliation":[{"name":"Dept. of Microbiology, Institute for Applied Biosciences Karlsruhe Institute of Technology (KIT) \u2010 South Campus  Karlsruhe Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Leyao","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, Institute of Pharmaceutical Biology 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