{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T18:49:47Z","timestamp":1792003787758,"version":"4.4.0"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"40","license":[{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T00:00:00Z","timestamp":1791158400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22277075"],"award-info":[{"award-number":["22277075"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22307076"],"award-info":[{"award-number":["22307076"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["32425033"],"award-info":[{"award-number":["32425033"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82404485"],"award-info":[{"award-number":["82404485"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010031","name":"Postdoctoral Research Foundation of China","doi-asserted-by":"publisher","award":["2024M761990"],"award-info":[{"award-number":["2024M761990"]}],"id":[{"id":"10.13039\/501100010031","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2025YFA0921000"],"award-info":[{"award-number":["2025YFA0921000"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Yunnan Province","doi-asserted-by":"publisher","award":["202505AF350066"],"award-info":[{"award-number":["202505AF350066"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,14]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Cytochrome P450 dimerases generate the remarkable structural diversity of dimeric diketopiperazine (DKP) natural products through highly selective intermolecular radical-mediated reactions. Although radical addition mechanisms have been established for most bacterial DKP dimerization modes, the molecular basis underlying the formation of the unusual C3\u2013N1\u2032 linkage has remained unresolved, preventing a unified mechanistic understanding of P450-catalyzed DKP dimerization. Here, we combine structure-guided protein engineering, X-ray crystallography, biochemical characterization, molecular dynamics simulations, and QM\/MM calculations to elucidate the mechanism of the C3\u2013N1\u2032 dimerase using an engineered soluble surrogate derived from its C3\u2013C3\u2032 homolog TtpB1. We show that C3\u2013N1\u2032 bond formation proceeds through a previously unrecognized diradical coupling mechanism, in which sequential hydrogen atom abstraction generates discrete N10- and N1\u2032-centered radicals prior to intramolecular cyclization and intermolecular radical coupling. This pathway is fundamentally distinct from the radical addition mechanism employed by all previously characterized bacterial DKP dimerases. Guided by these mechanistic insights, we further reprogram a single P450 scaffold to catalyze four distinct intermolecular coupling modes, including native C3\u2013C3\u2032 and engineered C3\u2013N1\u2032, N1\u2013C7\u2032, and C3\u2013C7\u2032 linkages. Together, these findings reveal that divergent DKP dimerization is governed by a tunable radical addition\u2013diradical coupling switch operating on a conserved substrate-binding architecture, establishing a unified mechanistic framework for cytochrome P450-catalyzed DKP dimer biosynthesis and providing a blueprint for engineering new radical-mediated oxidative coupling reactions.<\/jats:p>","DOI":"10.1021\/jacs.6c16809","type":"journal-article","created":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T06:02:36Z","timestamp":1791180156000},"page":"43895-43906","source":"Crossref","is-referenced-by-count":0,"title":["A Radical Addition\u2013Diradical\nCoupling Switch\nUnifies Cytochrome P450-Catalyzed Diketopiperazine Dimerization"],"prefix":"10.1021","volume":"148","author":[{"given":"Yeqing","family":"Du","sequence":"first","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]},{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 201203"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tai-Ping","family":"Zhou","sequence":"additional","affiliation":[{"name":"Chengdu University of Traditional Chinese Medicine , , ,","place":["Chengdu, China, 611137"]},{"name":"Xiamen University , , ,","place":["Xiamen, China, 361005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenya","family":"Tian","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]},{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 201203"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zixin","family":"Deng","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5967-3168","authenticated-orcid":true,"given":"Guangzheng","family":"Wei","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]},{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 201203"]},{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3353-9411","authenticated-orcid":true,"given":"Binju","family":"Wang","sequence":"additional","affiliation":[{"name":"Xiamen University , , ,","place":["Xiamen, China, 361005"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3301-8536","authenticated-orcid":true,"given":"Xudong","family":"Qu","sequence":"additional","affiliation":[{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 200240"]},{"name":"Shanghai Jiao Tong University , , ,","place":["Shanghai, China, 201203"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,5]]},"reference":[{"issue":"5","key":"2026101414095557400_cit1","doi-asserted-by":"publisher","first-page":"1388","DOI":"10.1002\/chem.201001451","article-title":"Structure,\nBioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b]indole","volume":"17","author":"Ruiz-Sanchis","year":"2011","journal-title":"Chem.\u2500Eur. J."},{"issue":"2","key":"2026101414095557400_cit2","doi-asserted-by":"publisher","first-page":"151","DOI":"10.1021\/ar050175j","article-title":"Chemistry of the Hexahydropyrrolo[2,3-b]indoles: configuration,\nconformation, reactivity, and applications in synthesis","volume":"40","author":"Crich","year":"2007","journal-title":"Acc. Chem. Res."},{"issue":"7","key":"2026101414095557400_cit3","doi-asserted-by":"publisher","first-page":"3641","DOI":"10.1021\/cr200398y","article-title":"2,5-Diketopiperazines:\nsynthesis, reactions, medicinal chemistry, and bioactive natural products","volume":"112","author":"Borthwick","year":"2012","journal-title":"Chem. Rev."},{"issue":"35","key":"2026101414095557400_cit4","doi-asserted-by":"publisher","first-page":"6659","DOI":"10.1021\/acs.jafc.6b01772","article-title":"Structural diversity\nand biological activities of indole diketopiperazine alkaloids from\nfungi","volume":"64","author":"Ma","year":"2016","journal-title":"J. Agric. Food Chem."},{"issue":"21","key":"2026101414095557400_cit5","doi-asserted-by":"publisher","first-page":"7585","DOI":"10.3390\/molecules27217585","article-title":"Bispyrrolidinoindoline epi(poly)thiodioxopiperazines\n(BPI-ETPs) and simplified mimetics: structural characterization, bioactivities,\nand total synthesis","volume":"27","author":"Marti\u0301nez","year":"2022","journal-title":"Molecules"},{"issue":"9","key":"2026101414095557400_cit6","doi-asserted-by":"publisher","first-page":"1327","DOI":"10.1039\/D3NP00068K","article-title":"Verticillins: fungal\nepipolythiodioxopiperazine alkaloids with chemotherapeutic potential","volume":"41","author":"Pierre","year":"2024","journal-title":"Nat. Prod. Rep."},{"issue":"9","key":"2026101414095557400_cit7","doi-asserted-by":"publisher","first-page":"1721","DOI":"10.1039\/D2NP00030J","article-title":"Biosynthesis of pyrroloindoline-containing\nnatural products","volume":"39","author":"Sun","year":"2022","journal-title":"Nat. Prod. 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Am. Chem.\nSoc."},{"issue":"3","key":"2026101414095557400_cit16","doi-asserted-by":"publisher","first-page":"1057","DOI":"10.1021\/jacs.5b12392","article-title":"Concise total\nsynthesis of (+)-asperazine,\n(+)-pestalazine A, and (+)-iso-pestalazine A. Structure revision of\n(+)-pestalazine A","volume":"138","author":"Loach","year":"2016","journal-title":"J. Am. Chem. Soc."},{"issue":"33","key":"2026101414095557400_cit17","doi-asserted-by":"publisher","first-page":"13002","DOI":"10.1021\/ja2057852","article-title":"Directed\nheterodimerization: stereocontrolled\nassembly via solvent-caged unsymmetrical diazene fragmentation","volume":"133","author":"Movassaghi","year":"2011","journal-title":"J. Am. Chem. Soc."},{"issue":"4","key":"2026101414095557400_cit18","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202521607","article-title":"Total syntheses of diketopiperazine\nalkaloids via divergent C3\u2212N1\u2019 and C3\u2212C5\u2019 bond anchor","volume":"65","author":"Fu","year":"2026","journal-title":"Angew. Chem.,\nInt. Ed."},{"issue":"2","key":"2026101414095557400_cit19","doi-asserted-by":"publisher","first-page":"483","DOI":"10.1016\/j.chempr.2022.10.021","article-title":"Total synthesis\nof (+)-asperazine A: A stereoselective\ndomino dimerization","volume":"9","author":"Bai","year":"2023","journal-title":"Chem"},{"issue":"1","key":"2026101414095557400_cit20","doi-asserted-by":"publisher","first-page":"4428","DOI":"10.1038\/s41467-018-06528-z","article-title":"Efficient biosynthesis\nof heterodimeric C3-aryl pyrroloindoline alkaloids","volume":"9","author":"Tian","year":"2018","journal-title":"Nat. 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Chem."},{"issue":"21","key":"2026101414095557400_cit23","doi-asserted-by":"publisher","first-page":"18450","DOI":"10.1021\/acscatal.5c06701","article-title":"Rational mining\nand engineering of unique P450 enzymes enable production\nof diverse dimeric tryptophan-containing diketopiperazine alkaloids","volume":"15","author":"Yu","year":"2025","journal-title":"ACS Catal."},{"issue":"1","key":"2026101414095557400_cit24","doi-asserted-by":"publisher","first-page":"6251","DOI":"10.1038\/s41467-020-20022-5","article-title":"Molecular\nbasis of regio- and stereo-specificity in biosynthesis of bacterial\nheterodimeric diketopiperazines","volume":"11","author":"Sun","year":"2020","journal-title":"Nat. Commun."},{"issue":"46","key":"2026101414095557400_cit25","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2412890121","article-title":"A nucleobase-driven\nP450 peroxidase system enables regio- and stereo-specific formation\nof C\u2212C and C\u2212N bonds","volume":"121","author":"Wei","year":"2024","journal-title":"Proc. Natl.\nAcad. Sci. U.S.A."},{"issue":"41","key":"2026101414095557400_cit26","doi-asserted-by":"publisher","first-page":"17413","DOI":"10.1021\/jacs.0c06312","article-title":"Structure and function of NzeB, a versatile C\u2212C\nand C\u2212N bond-forming diketopiperazine dimerase","volume":"142","author":"Shende","year":"2020","journal-title":"J. Am. Chem. Soc."},{"issue":"5","key":"2026101414095557400_cit27","doi-asserted-by":"publisher","first-page":"656","DOI":"10.1002\/cbic.201300751","article-title":"Cytochrome P450 as dimerization catalyst in diketopiperazine\nalkaloid biosynthesis","volume":"15","author":"Saruwatari","year":"2014","journal-title":"ChemBioChem"},{"issue":"26","key":"2026101414095557400_cit28","doi-asserted-by":"publisher","first-page":"2310018","DOI":"10.1002\/advs.202310018","article-title":"Exploring\nthe diverse landscape of fungal cytochrome P450-catalyzed regio- and\nstereoselective dimerization of diketopiperazines","volume":"11","author":"Ma","year":"2024","journal-title":"Adv. Sci."},{"issue":"17","key":"2026101414095557400_cit29","doi-asserted-by":"publisher","first-page":"7094","DOI":"10.1021\/acs.orglett.9b02666","article-title":"Two cytochrome P450\nenzymes from Streptomyces sp. NRRL S-1868 catalyze\ndistinct dimerization of tryptophan-containing\ncyclodipeptides","volume":"21","author":"Yu","year":"2019","journal-title":"Org. Lett."},{"issue":"17","key":"2026101414095557400_cit30","doi-asserted-by":"publisher","first-page":"6601","DOI":"10.1021\/acs.orglett.1c01022","article-title":"Global genome mining\nreveals a cytochrome P450-catalyzed\ncyclization of crownlike cyclodipeptides with neuroprotective activity","volume":"23","author":"Malit","year":"2021","journal-title":"Org. Lett."},{"issue":"75","key":"2026101414095557400_cit31","doi-asserted-by":"publisher","first-page":"11042","DOI":"10.1039\/D0CC04772D","article-title":"Increasing cytochrome P450 enzyme\ndiversity by identification\nof two distinct cyclodipeptide dimerases","volume":"56","author":"Liu","year":"2020","journal-title":"Chem.\nCommun."},{"issue":"4","key":"2026101414095557400_cit32","doi-asserted-by":"publisher","first-page":"1591","DOI":"10.1021\/jacsau.4c00075","article-title":"Substrate\nconformational switch enables the stereoselective dimerization in\nP450 NascB: Insights from molecular dynamics simulations and quantum\nmechanical\/molecular mechanical calculations","volume":"4","author":"Zhou","year":"2024","journal-title":"JACS Au"},{"issue":"20","key":"2026101414095557400_cit33","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202210254","article-title":"Molecular\ndynamics simulations guide chimeragenesis and engineered control of\nchemoselectivity in diketopiperazine dimerases","volume":"62","author":"Shende","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"issue":"35","key":"2026101414095557400_cit34","doi-asserted-by":"publisher","first-page":"19256","DOI":"10.1021\/jacs.3c04542","article-title":"A ferric-superoxide\nintermediate initiates P450-catalyzed cyclic dipeptide dimerization","volume":"145","author":"Gering","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"49","key":"2026101414095557400_cit35","doi-asserted-by":"publisher","first-page":"45199","DOI":"10.1021\/jacs.5c14741","article-title":"P450-mediated dual\ncyclization mechanisms for pyrroloindoline unit formation in bispyrrolidinoindoline\ndiketopiperazine alkaloid biosynthesis","volume":"147","author":"Du","year":"2025","journal-title":"J. Am.\nChem. Soc."},{"key":"2026101414095557400_cit36","doi-asserted-by":"publisher","first-page":"113249","DOI":"10.1016\/j.comptc.2021.113249","article-title":"A general\ncode for calculating molecular thermochemistry\nproperties","volume":"1200","author":"Lu","year":"2021","journal-title":"Comput. Theor. Chem."},{"issue":"5","key":"2026101414095557400_cit37","doi-asserted-by":"publisher","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."},{"key":"2026101414095557400_cit38","unstructured":"Lu, T.\n          \n          Molclus Program, Version 1.14, 2026. http:\/\/www.keinsci.com\/research\/molclus.html (accessed 2026-05-21)."},{"issue":"1","key":"2026101414095557400_cit39","doi-asserted-by":"publisher","first-page":"25","DOI":"10.1021\/acs.jnatprod.1c00526","article-title":"A molecular\nnetworking based discovery of diketopiperazine heterodimers and aspergillicins\nfrom aspergillus caelatus","volume":"85","author":"Wang","year":"2022","journal-title":"J. Nat. Prod."},{"issue":"17","key":"2026101414095557400_cit40","doi-asserted-by":"publisher","first-page":"17339","DOI":"10.1021\/acscatal.6c04534","article-title":"Probing the catalytic\npromiscuity and enhancing the efficiency of\nCYP725A4 with a taxadiene substrate mimic","volume":"16","author":"Huang","year":"2026","journal-title":"ACS\nCatal."},{"issue":"3","key":"2026101414095557400_cit41","doi-asserted-by":"publisher","first-page":"764","DOI":"10.1002\/anie.201812093","article-title":"Chemo- and regioselective dihydroxylation of benzene\nto hydroquinone enabled by engineered cytochrome P450 monooxygenase","volume":"58","author":"Zhou","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"issue":"19","key":"2026101414095557400_cit42","doi-asserted-by":"publisher","first-page":"14274","DOI":"10.1021\/acscatal.4c03875","article-title":"Molecular basis for the P450-catalyzed sp3 C\u2212N glycosidic\nbond formation in staurosporine biosynthesis","volume":"14","author":"Xiao","year":"2024","journal-title":"ACS Catal."},{"issue":"13","key":"2026101414095557400_cit43","doi-asserted-by":"publisher","first-page":"7252","DOI":"10.1021\/jacs.2c12962","article-title":"How the conformational\nmovement of the substrate drives the regioselective C\u2212N bond\nformation in P450 TleB: Insights from molecular dynamics simulations\nand quantum mechanical\/molecular mechanical calculations","volume":"145","author":"Wang","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"1","key":"2026101414095557400_cit44","doi-asserted-by":"publisher","first-page":"216","DOI":"10.1021\/jacs.8b08864","article-title":"Binding of distinct\nsubstrate conformations enables hydroxylation of remote sites in thaxtomin\nd by cytochrome P450 TxtC","volume":"141","author":"Alkhalaf","year":"2019","journal-title":"J. Am. Chem. Soc."},{"issue":"2","key":"2026101414095557400_cit45","doi-asserted-by":"publisher","first-page":"490","DOI":"10.1021\/acs.biochem.4c00665","article-title":"Understanding the scope\nof cytochrome P450-catalyzed radical dimerization of diketopiperazines","volume":"64","author":"Sato","year":"2025","journal-title":"Biochemistry"},{"issue":"8","key":"2026101414095557400_cit46","doi-asserted-by":"publisher","first-page":"1078","DOI":"10.3390\/molecules21081078","article-title":"Evaluation of biosynthetic\npathway and engineered biosynthesis of alkaloids","volume":"21","author":"Kishimoto","year":"2016","journal-title":"Molecules"}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c16809","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/40\/43895\/68741022\/jacs.6c16809.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/40\/43895\/68741022\/jacs.6c16809.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T18:21:53Z","timestamp":1792002113000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/40\/43895\/5444292\/A-Radical-Addition-Diradical-Coupling-Switch"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,5]]},"references-count":46,"journal-issue":{"issue":"40","published-online":{"date-parts":[[2026,10,5]]},"published-print":{"date-parts":[[2026,10,14]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c16809","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,5]]}}}