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d0np00063a

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Enzymaticdimerizationinthebiosyntheticpathwayofmicrobialnaturalproducts†JiawangLiu,‡AnanLiu‡andYoucaiHu*Covering:uptoAugust2020Thedramaticincreaseintheidentificationofdimericnaturalproductsgeneratedbymicroorganismsandplantshasplayedasignificantroleindrugdiscovery.Thebiosyntheticpathwaysoftheseproductsfeatureinherentdimerizationreactions,whicharevaluableforbiosyntheticapplicationsandchemicaltransformations.Theextraordinarymechanismsofthedimerizationofsecondarymetabolitesshouldadvanceourunderstandingoftheuncommonchemicalrulesfornaturalproductbiosynthesis,whichwill,inturn,acceleratethediscoveryofdimericreactionsandmoleculesinnatureandprovidepromisingstrategiesforthetotalsynthesisofnaturalproductsthroughdimerization.Thisreviewfocusesontheenzymesinvolvedinthedimerizationinthebiosyntheticpathwayofmicrobialnaturalproducts,withanemphasisoncytochromeP450s,laccases,andintermolecular[4+2]cyclases,alongwithotheratypicalenzymes.Theidentification,characterization,andcatalyticlandscapesoftheseenzymesarealsointroduced.1Introduction2CytochromeP450-catalyzeddimerization2.1C–Ccoupling2.1.1Biarylcoupling2.1.1.1Anthraquinones2.1.1.2Xanthones2.1.1.3Naphthalenesandnaphtho-g-pyrones2.1.1.4Coumarins2.1.1.5Cyclopeptides2.1.1.6Polybrominatedmarinenaturalproducts2.1.1.7Dityrosineandxanthocillin2.1.2Non-biarylcoupling2.1.2.1Diketopiperazinealkaloids2.1.2.2Duclauxins2.1.2.3CommunesinA2.2Carbon–heteroatomcoupling2.3AnalysisofthemechanismofP450-mediateddimerization2.3.1Diradicalcouplinginthedimerizationofphenolicnaturalproducts2.3.2Radicalmechanismorcationicmechanisminthedimerizationofazacyclicnaturalproducts3Laccase-catalyzedoxidativedimerization3.1Laccasesandlaccase/auxiliaryproteinsystems3.2Laccase/fasciclin-domain-containingproteinsystems3.3Laccase/berberinebridgeenzyme-likeoxidasesystems4Intermolecular[4+2]cyclization4.1Macrophomatesynthase4.2Riboavinsynthase4.3Hetero-Diels-Alderase5Dimerizationcatalyzedbyotherenzymes5.1Etherbondgenerationinthebiosynthesisoffungaldiphenylethers(DPEs)5.2NRPS-li

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