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Here, we report a comprehensive mechanistic study of this unique transformation catalyzed by the Fe\/2OG enzyme Hvm1, using a combination of deuterated substrates, substrate analogs bearing electron-withdrawing substituents, and multiple spectroscopic methods (LC-MS, X-ray crystallography, CD spectroscopy, and NMR). The reaction proceeds via consecutive radicaloid C\u2013C (C3\u2032\u2013C2 and C3\u2013C3\u2033) couplings, involving sequential radical attack on the olefin and benzoyl group (Minisci variant), initiated by a C3\u2032 radical generated through C3\u2032 pro-S hydrogen atom transfer (HAT). The first C\u2013C bond (C3\u2032\u2013C2) is formed on the Si-face of C2 with retention of C3\u2032 configuration. The second C\u2013C bond (C3\u2013C3\u2033) formation can proceed with either of two stereochemical senses\u2500antarafacial or suprafacial\u2500relative to the first newly formed C3\u2032\u2013C2 bond: the antarafacial pathway leads to helvamide B, while the suprafacial pathway affords the previously unreported epimer, helvamide A. Crystal structure analysis identifies Y67 as a key residue governing the partitioning of stereochemical outcomes in the second C\u2013C bond formation. Furthermore, the conclusive stereochemical assignment of helvamide B corrects the prior misassignment of the C3\u2032 configuration in the arizonamides.<\/jats:p>","DOI":"10.1021\/jacs.6c05166","type":"journal-article","created":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T21:01:33Z","timestamp":1786741293000},"page":"35399-35410","source":"Crossref","is-referenced-by-count":0,"title":["Radical Mechanism and\nStereochemical Control in Consecutive\nC\u2013C Bond Formation by the Nonheme Iron Enzyme Hvm1"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1127-1829","authenticated-orcid":true,"given":"Shengbin","family":"Zhou","sequence":"first","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiapeng","family":"Zhang","sequence":"additional","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jia-Yu","family":"Zuo","sequence":"additional","affiliation":[{"name":"Jinan University , , ,","place":["Guangzhou, China, 510632"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianchang","family":"Yu","sequence":"additional","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi-Fan","family":"Du","sequence":"additional","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rui","family":"Wang","sequence":"additional","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chengkai","family":"Wu","sequence":"additional","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ganlu","family":"Zhang","sequence":"additional","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aolong","family":"Shang","sequence":"additional","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peihong","family":"Zhou","sequence":"additional","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8781-3394","authenticated-orcid":true,"given":"Yuwen","family":"Wang","sequence":"additional","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5088-5869","authenticated-orcid":true,"given":"Zhi-Min","family":"Zhang","sequence":"additional","affiliation":[{"name":"Jinan University , , ,","place":["Guangzhou, China, 510632"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3367-6659","authenticated-orcid":true,"given":"Hang","family":"Li","sequence":"additional","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3685-6268","authenticated-orcid":true,"given":"Hong","family":"Liu","sequence":"additional","affiliation":[{"name":"University of Chinese Academy of Sciences , , ,","place":["Hangzhou, China, 310024"]},{"name":"Chinese Academy of Sciences , , 555 Zu Chong Zhi Road , ,","place":["Shanghai, China, 201203"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,14]]},"reference":[{"key":"2026090104504983900_cit1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pharmthera.2024.108752","article-title":"New drug discovery and\ndevelopment from natural products: Advances and strategies","volume":"264","author":"Wang","year":"2024","journal-title":"Pharmacol. 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Chem.\nSoc."},{"issue":"6175","key":"2026090104504983900_cit10","doi-asserted-by":"publisher","first-page":"1140","DOI":"10.1126\/science.1248000","article-title":"Mechanism of the C5 stereoinversion reaction\nin the biosynthesis of carbapenem antibiotics","volume":"343","author":"Chang","year":"2014","journal-title":"Science"},{"issue":"2","key":"2026090104504983900_cit11","doi-asserted-by":"publisher","first-page":"238","DOI":"10.1021\/acsbiomedchemau.5c00001","article-title":"Discovery of Noncanonical Iron and\n2-Oxoglutarate Dependent Enzymes Involved in C-C and C-N Bond Formation\nin Biosynthetic Pathways","volume":"5","author":"Shen","year":"2025","journal-title":"ACS Biomed. Chem.\nAu."},{"issue":"7","key":"2026090104504983900_cit12","doi-asserted-by":"publisher","first-page":"484","DOI":"10.1021\/ar700066p","article-title":"Non-heme Fe(IV)-oxo intermediates","volume":"40","author":"Krebs","year":"2007","journal-title":"Acc. Chem. 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Chem.\nSoc."},{"issue":"1","key":"2026090104504983900_cit15","doi-asserted-by":"publisher","first-page":"278","DOI":"10.1021\/acscatal.0c03879","article-title":"Deciphering Pyrrolidine and Olefin Formation\nMechanism in Kainic Acid Biosynthesis","volume":"11","author":"Chen","year":"2021","journal-title":"ACS Catal."},{"issue":"10","key":"2026090104504983900_cit16","doi-asserted-by":"publisher","first-page":"1328","DOI":"10.1039\/C4NP00062E","article-title":"Biosynthesis of the ergot alkaloids","volume":"31","author":"Jakubczyk","year":"2014","journal-title":"Nat. Prod. Rep."},{"issue":"1","key":"2026090104504983900_cit17","doi-asserted-by":"publisher","first-page":"228","DOI":"10.1021\/acs.orglett.8b03670","article-title":"Reaction Mechanism\nof a Nonheme Iron Enzyme Catalyzed Oxidative Cyclization via C-C Bond\nFormation","volume":"21","author":"Chang","year":"2019","journal-title":"Org. Lett."},{"issue":"34","key":"2026090104504983900_cit18","doi-asserted-by":"publisher","first-page":"11657","DOI":"10.1002\/anie.201904102","article-title":"Asymmetric\nchemoenzymatic synthesis\nof (\u2212)-podophyllotoxin and related aryltetralin lignans","volume":"58","author":"Li","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"issue":"30","key":"2026090104504983900_cit19","doi-asserted-by":"publisher","first-page":"13948","DOI":"10.1021\/acs.inorgchem.4c01263","article-title":"Unraveling the Mechanism\nof the Oxidative C\u2013C Bond Coupling\nReaction Catalyzed by Deoxypodophyllotoxin Synthase","volume":"63","author":"Su","year":"2024","journal-title":"Inorg. Chem."},{"issue":"1","key":"2026090104504983900_cit20","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.2113770119","article-title":"Mechanistic analysis\nof carbon-carbon bond formation by deoxypodophyllotoxin synthase","volume":"119","author":"Tang","year":"2022","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"issue":"14","key":"2026090104504983900_cit21","doi-asserted-by":"publisher","first-page":"2998","DOI":"10.1111\/febs.15192","article-title":"Evolution-guided\nengineering\nof non-heme iron enzymes involved in nogalamycin biosynthesis","volume":"287","author":"Wandi","year":"2020","journal-title":"FEBA J."},{"issue":"30","key":"2026090104504983900_cit22","doi-asserted-by":"publisher","first-page":"9743","DOI":"10.1021\/jacs.8b06084","article-title":"Structural and Computational\nBases for Dramatic Skeletal Rearrangement in Anditomin Biosynthesis","volume":"140","author":"Nakashima","year":"2018","journal-title":"J. Am. Chem. Soc."},{"issue":"2","key":"2026090104504983900_cit23","doi-asserted-by":"publisher","first-page":"387","DOI":"10.1039\/D2NP00070A","article-title":"Discovery, bioactivity\nand biosynthesis of fungal piperazines","volume":"40","author":"Wang","year":"2023","journal-title":"Nat.\nProd. 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Antibiot."},{"issue":"3","key":"2026090104504983900_cit26","doi-asserted-by":"publisher","first-page":"2610","DOI":"10.1021\/acs.jmedchem.1c01989","article-title":"Neochrysosporazines:\nPrecursor-Directed Biosynthesis Defines a Marine-Derived Fungal Natural\nProduct P-Glycoprotein Inhibitory Pharmacophore","volume":"65","author":"Dewa","year":"2022","journal-title":"J. Med. Chem."},{"issue":"9","key":"2026090104504983900_cit27","doi-asserted-by":"publisher","first-page":"1807","DOI":"10.1021\/acs.orglett.3c04310","article-title":"Heterologous biosynthesis\nof the sterol O-acyltransferase inhibitor helvamide\nunveils an \u03b1-ketoglutarate-dependent cross-linking oxygenase","volume":"26","author":"Wang","year":"2024","journal-title":"Org. Lett."},{"issue":"20","key":"2026090104504983900_cit28","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202401324","article-title":"Non-Heme Iron Enzymes\nCatalyze Heterobicyclic and Spirocyclic Isoquinolone Core Formation\nin Piperazine Alkaloid Biosynthesis","volume":"63","author":"Pham","year":"2024","journal-title":"Angew.\nChem., Int. Ed."},{"issue":"20","key":"2026090104504983900_cit29","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202301091","article-title":"Cobalt-Catalyzed Asymmetric\nDeuteration of \u03b1-Amidoacrylates for Stereoselective Synthesis\nof \u03b1,\u03b2-Dideuterated \u03b1-Amino Acids","volume":"135","author":"Li","year":"2023","journal-title":"Angew. Chem., Int. 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Biol."},{"issue":"1","key":"2026090104504983900_cit33","doi-asserted-by":"publisher","first-page":"7","DOI":"10.1016\/S0014-5793(02)02520-6","article-title":"Crystal\nstructure of\na clavaminate synthase\u2013Fe(II)\u20132-oxoglutarate\u2013substrate\u2013NO\ncomplex: evidence for metal centred rearrangements","volume":"517","author":"Zhang","year":"2002","journal-title":"FEBS Lett."},{"issue":"35","key":"2026090104504983900_cit34","doi-asserted-by":"publisher","first-page":"24271","DOI":"10.1021\/jacs.4c04406","article-title":"Optimized\nSubstrate\nPositioning Enables Switches in the C\u2013H Cleavage Site and Reaction\nOutcome in the Hydroxylation\u2013Epoxidation Sequence Catalyzed\nby Hyoscyamine 6\u03b2-Hydroxylase","volume":"146","author":"Wenger","year":"2024","journal-title":"J. Am.\nChem. Soc."},{"issue":"39","key":"2026090104504983900_cit35","doi-asserted-by":"publisher","first-page":"13830","DOI":"10.1021\/jacs.7b07374","article-title":"Visualizing the Reaction\nCycle in an Iron(II)- and 2-(Oxo)-glutarate-Dependent Hydroxylase","volume":"139","author":"Mitchell","year":"2017","journal-title":"J. Am. Chem. Soc."},{"issue":"21","key":"2026090104504983900_cit36","doi-asserted-by":"publisher","first-page":"13382","DOI":"10.1021\/acs.inorgchem.7b02113","article-title":"Vanadyl as a Stable\nStructural Mimic of Reactive Ferryl Intermediates in Mononuclear Nonheme-Iron\nEnzymes","volume":"56","author":"Martinie","year":"2017","journal-title":"Inorg. Chem."},{"issue":"47","key":"2026090104504983900_cit37","doi-asserted-by":"publisher","first-page":"21512","DOI":"10.1021\/jacs.2c08116","article-title":"Stereoselectivity and\nSubstrate Specificity of the Fe(II)\/\u03b1-Ketoglutarate-Dependent\nOxygenase TqaL","volume":"144","author":"Tao","year":"2022","journal-title":"J. Am. Chem. Soc."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c05166","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/33\/35399\/66568862\/jacs.6c05166.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/33\/35399\/66568862\/jacs.6c05166.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T08:50:57Z","timestamp":1788252657000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/33\/35399\/5256826\/Radical-Mechanism-and-Stereochemical-Control-in"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,14]]},"references-count":37,"journal-issue":{"issue":"33","published-online":{"date-parts":[[2026,8,14]]},"published-print":{"date-parts":[[2026,8,26]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c05166","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,14]]}}}