{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T19:46:12Z","timestamp":1792784772751,"version":"4.5.0"},"reference-count":56,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T00:00:00Z","timestamp":1791504000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T00:00:00Z","timestamp":1791504000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T00:00:00Z","timestamp":1791504000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100003399","name":"Science and Technology Commission of Shanghai Municipality","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003399","id-type":"DOI","asserted-by":"publisher"}]},{"name":"National Natural Science Foundation of China (NSFC)","award":["22137009"],"award-info":[{"award-number":["22137009"]}],"id":[{"id":"https:\/\/ror.org\/01h0zpd94","id-type":"ROR","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,21]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Halogenated compounds are prevalent in natural and synthetic molecules, profoundly affecting molecular stability, physicochemical properties, and biological activity. While enzymatic halogenation offers a sustainable and selective synthetic route, its broad application is limited by the narrow substrate scope of the known halogenases. Here, we identify and characterize a new secreted vanadium-dependent haloperoxidase (VHPO), XhnO11, from Streptomyces xinghaiensis S187, which catalyzes a critical chlorination step in the biosynthesis of the potent anticancer agent xinghaicarcin A. Through X-ray crystallography, molecular docking, and mutagenesis, we uncovered distinct mechanism features underlying bromination and revealed an unusually spacious active site in XhnO11. These structural characteristics enable remarkable substrate promiscuity, accommodating a diverse range of aromatic scaffolds, including anthracyclines, xanthones, flavonoids, and nitroaromatics. Furthermore, XhnO11 efficiently mediates mono-, di-, and multibromination of tyrosine, tyrosine-containing peptides, and tryptophan-derived substrates. Collectively, these findings expand the functional scope of VHPOs and establish XhnO11 as a versatile and broadly tolerant biocatalyst, facilitating mining of new halogenated natural products and providing a powerful tool for the selective functionalization of diverse bioactive molecules.<\/jats:p>","DOI":"10.1021\/jacs.6c16767","type":"journal-article","created":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T10:02:00Z","timestamp":1791540120000},"page":"45103-45112","source":"Crossref","is-referenced-by-count":0,"title":["A Substrate-Permissive\nVanadium Haloperoxidase in\nType II Polyketide Biosynthesis Unlocks Non-Native Halogenation across\nDiverse Substrate Scaffolds"],"prefix":"10.1021","volume":"148","author":[{"given":"Shi-Qi","family":"Fang","sequence":"first","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dian","family":"Ding","sequence":"additional","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiu-Yue","family":"Nie","sequence":"additional","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shu-Ya","family":"Peng","sequence":"additional","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu","family":"Hu","sequence":"additional","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ya-Ping","family":"Rong","sequence":"additional","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jing","family":"Wang","sequence":"additional","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lian","family":"Wu","sequence":"additional","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3149-4683","authenticated-orcid":true,"given":"Gong-Li","family":"Tang","sequence":"additional","affiliation":[{"name":"University of CAS , , ,","place":["Shanghai, China, 200032"]},{"name":"University of CAS , , ,","place":["Hangzhou, China, 310024"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,9]]},"reference":[{"key":"2026102111083247700_cit1","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1007\/978-3-031-26629-4_1","article-title":"Naturally Occurring\nOrganohalogen Compounds-A Comprehensive Review","volume-title":"Naturally Occurring Organohalogen Compounds","author":"Gribble","year":"2023"},{"issue":"10","key":"2026102111083247700_cit2","doi-asserted-by":"publisher","first-page":"1441","DOI":"10.1021\/ed081p1441","article-title":"Natural\nOrganohalogens: A New Frontier for Medicinal Agents?","volume":"81","author":"Gribble","year":"2004","journal-title":"J. Chem. Educ."},{"issue":"1","key":"2026102111083247700_cit3","doi-asserted-by":"publisher","first-page":"232","DOI":"10.1021\/acs.chemrev.7b00032","article-title":"Development\nof Halogenase Enzymes for Use in Synthesis","volume":"118","author":"Latham","year":"2018","journal-title":"Chem. Rev."},{"issue":"34","key":"2026102111083247700_cit4","doi-asserted-by":"publisher","first-page":"11009","DOI":"10.1002\/anie.201804351","article-title":"Total Synthesis\nEstablishes the Biosynthetic\nPathway to the Naphterpin and Marinone Natural Products","volume":"57","author":"Murray","year":"2018","journal-title":"Angew. Chem., Int. Ed."},{"issue":"5744","key":"2026102111083247700_cit5","doi-asserted-by":"publisher","first-page":"2216","DOI":"10.1126\/science.1116510","article-title":"Tryptophan 7-Halogenase (PrnA) Structure Suggests a\nMechanism for Regioselective Chlorination","volume":"309","author":"Dong","year":"2005","journal-title":"Science"},{"issue":"1","key":"2026102111083247700_cit6","doi-asserted-by":"publisher","first-page":"1255","DOI":"10.1038\/s41467-019-09215-9","article-title":"Unusual Substrate\nand Halide Versatility of Phenolic\nHalogenase PltM","volume":"10","author":"Mori","year":"2019","journal-title":"Nat. Commun."},{"issue":"22","key":"2026102111083247700_cit7","doi-asserted-by":"publisher","first-page":"6374","DOI":"10.1002\/anie.201509573","article-title":"Specific Enzymatic\nHalogenation\u2500From\nthe Discovery of Halogenated Enzymes to Their Applications In Vitro\nand In Vivo","volume":"55","author":"Weichold","year":"2016","journal-title":"Angew. Chem., Int. Ed."},{"issue":"15","key":"2026102111083247700_cit8","doi-asserted-by":"publisher","first-page":"2129","DOI":"10.1002\/cbic.201500338","article-title":"Halogenase\nEngineering for the Generation of New Natural\nProduct Analogues","volume":"16","author":"Brown","year":"2015","journal-title":"ChemBioChem"},{"issue":"12","key":"2026102111083247700_cit9","doi-asserted-by":"publisher","first-page":"687","DOI":"10.1038\/s41570-019-0143-x","article-title":"The Importance\nof Catalytic Promiscuity\nfor Enzyme Design and Evolution","volume":"3","author":"Leveson-Gower","year":"2019","journal-title":"Nat. Rev. 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Biol."},{"issue":"8049","key":"2026102111083247700_cit12","doi-asserted-by":"publisher","first-page":"126","DOI":"10.1038\/s41586-024-08362-4","article-title":"Copper-Dependent\nHalogenase Catalyses Unactivated C\u2013H Bond Functionalization","volume":"638","author":"Chiang","year":"2025","journal-title":"Nature"},{"issue":"1","key":"2026102111083247700_cit13","doi-asserted-by":"publisher","first-page":"69","DOI":"10.1038\/nchembio.2007.56","article-title":"Discovery\nand Characterization\nof a Marine Bacterial SAM-Dependent Chlorinase","volume":"4","author":"Eusta\u0301quio","year":"2008","journal-title":"Nat. Chem. 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U.S.A."},{"issue":"29","key":"2026102111083247700_cit26","doi-asserted-by":"publisher","first-page":"11988","DOI":"10.1021\/ja305665f","article-title":"Cyclic Meroterpenoid Antibiotics\nBiosynthesized in Divergent Pathways with Vanadium-Dependent Chloroperoxidases","volume":"134","author":"Kaysser","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"2026102111083247700_cit27","doi-asserted-by":"publisher","first-page":"447","DOI":"10.1016\/bs.mie.2024.03.024","article-title":"Vanadium Haloperoxidases as Noncanonical Terpene Synthases","volume-title":"Methods in Enzymology","year":"2024"},{"issue":"17","key":"2026102111083247700_cit28","doi-asserted-by":"publisher","first-page":"1844","DOI":"10.1021\/acs.biochem.2c00338","article-title":"Structural Basis of Stereospecific\nVanadium-Dependent Haloperoxidase Family Enzymes in Napyradiomycin\nBiosynthesis","volume":"61","author":"Chen","year":"2022","journal-title":"Biochemistry"},{"issue":"7","key":"2026102111083247700_cit29","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202418843","article-title":"Functional\nCharacterization and Molecular Basis of a Multi-Site Halogenase in\nNaphthacemycin Biosynthesis","volume":"64","author":"Hu","year":"2025","journal-title":"Angew. Chem., Int.\nEd."},{"issue":"5","key":"2026102111083247700_cit30","doi-asserted-by":"publisher","first-page":"1394","DOI":"10.1021\/acs.jnatprod.9b00417","article-title":"Naphthacemycins from\na Streptomyces Sp. as Protein-Tyrosine Phosphatase\nInhibitors","volume":"83","author":"Huo","year":"2020","journal-title":"J. Nat. Prod."},{"issue":"2","key":"2026102111083247700_cit31","doi-asserted-by":"publisher","first-page":"232","DOI":"10.1128\/MMBR.65.2.232-260.2001","article-title":"Tetracycline Antibiotics:\nMode of Action, Applications,\nMolecular Biology, and Epidemiology of Bacterial Resistance","volume":"65","author":"Chopra","year":"2001","journal-title":"Microbiol. Mol. Biol. Rev."},{"issue":"1","key":"2026102111083247700_cit32","doi-asserted-by":"publisher","first-page":"119","DOI":"10.1021\/np980355k","article-title":"The Structure\nof Mithramycin Reinvestigated","volume":"62","author":"Wohlert","year":"1999","journal-title":"J. Nat. 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Coloproctol"},{"issue":"15","key":"2026102111083247700_cit35","doi-asserted-by":"publisher","first-page":"7381","DOI":"10.3390\/ijms26157381","article-title":"Isorhamnetin:\nReviewing Recent Developments in Anticancer\nMechanisms and Nanoformulation-Driven Delivery","volume":"26","author":"Rana","year":"2025","journal-title":"IJMS"},{"issue":"6","key":"2026102111083247700_cit36","doi-asserted-by":"publisher","first-page":"962","DOI":"10.1007\/s11095-010-0089-7","article-title":"Apigenin: A Promising\nMolecule for Cancer Prevention","volume":"27","author":"Shukla","year":"2010","journal-title":"Pharm. Res."},{"issue":"30","key":"2026102111083247700_cit37","doi-asserted-by":"publisher","first-page":"5574","DOI":"10.1039\/C4OB00474D","article-title":"Bis-Chlorination\nof a Hexapeptide\u2013PCP Conjugate by the Halogenase Involved in\nVancomycin Biosynthesis","volume":"12","author":"Schmartz","year":"2014","journal-title":"Org. Biomol. Chem."},{"issue":"8","key":"2026102111083247700_cit38","doi-asserted-by":"publisher","first-page":"2612","DOI":"10.1002\/chem.202003459","article-title":"Natural Products Originated\nfrom the Oxidative Coupling\nof Tyrosine and Tryptophan: Biosynthesis and Bioinspired Synthesis","volume":"27","author":"Tang","year":"2021","journal-title":"Chem.-Eur. J."},{"issue":"1","key":"2026102111083247700_cit39","doi-asserted-by":"publisher","first-page":"4843","DOI":"10.1038\/s41467-022-32535-2","article-title":"Halogenation\nof Tyrosine Perturbs Large-Scale Protein Self-Organization","volume":"13","author":"Sun","year":"2022","journal-title":"Nat. Commun."},{"issue":"1","key":"2026102111083247700_cit40","doi-asserted-by":"publisher","first-page":"232","DOI":"10.1021\/acs.chemrev.7b00032","article-title":"Development\nof Halogenase Enzymes for Use in Synthesis","volume":"118","author":"Latham","year":"2018","journal-title":"Chem. Rev."},{"key":"2026102111083247700_cit41","doi-asserted-by":"publisher","first-page":"69","DOI":"10.1016\/j.ymben.2013.06.003","article-title":"Deciphering\nand Engineering of the Final Step Halogenase for Improved Chlortetracycline\nBiosynthesis in Industrial Streptomyces Aureofaciens","volume":"19","author":"Zhu","year":"2013","journal-title":"Metab. Eng."},{"issue":"1","key":"2026102111083247700_cit42","doi-asserted-by":"publisher","first-page":"2083","DOI":"10.1038\/s41467-025-57023-1","article-title":"Unraveling the Molecular\nBasis of Substrate Specificity and Halogen Activation in Vanadium-Dependent\nHaloperoxidases","volume":"16","author":"Zeides","year":"2025","journal-title":"Nat. Commun."},{"issue":"12","key":"2026102111083247700_cit43","doi-asserted-by":"publisher","first-page":"8247","DOI":"10.1021\/acscatal.3c00761","article-title":"How Is Substrate Halogenation Triggered\nby the Vanadium\nHaloperoxidase from Curvularia Inaequalis","volume":"13","author":"Ge\u0301rard","year":"2023","journal-title":"ACS Catal."},{"issue":"16","key":"2026102111083247700_cit44","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.202400792","article-title":"Insights\ninto the Mechanism of a Vanadium Bromoperoxidase from the Marine Macro-Algae Corallina Pilulifera for Biocatalytic Halogenation","volume":"17","author":"Mitchell","year":"2025","journal-title":"ChemCatChem"},{"issue":"44","key":"2026102111083247700_cit45","doi-asserted-by":"publisher","first-page":"11232","DOI":"10.1073\/pnas.1800502115","article-title":"Extracellularly\nOxidative Activation and Inactivation of Matured Prodrug for Cryptic\nSelf-Resistance in Naphthyridinomycin Biosynthesis","volume":"115","author":"Zhang","year":"2018","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"issue":"8","key":"2026102111083247700_cit47","doi-asserted-by":"publisher","first-page":"4554","DOI":"10.1021\/acscatal.2c00485","article-title":"Chemoenzymatic Hunsdiecker-Type\nDecarboxylative Bromination of Cinnamic Acids","volume":"12","author":"Li","year":"2022","journal-title":"ACS Catal."},{"issue":"3","key":"2026102111083247700_cit48","doi-asserted-by":"publisher","first-page":"1733","DOI":"10.1021\/acscatal.3c05333","article-title":"Vanadium-Containing\nChloroperoxidase-Catalyzed Versatile Valorization of Phenols and Phenolic\nAcids","volume":"14","author":"Li","year":"2024","journal-title":"ACS Catal."},{"issue":"39","key":"2026102111083247700_cit49","doi-asserted-by":"publisher","first-page":"11089","DOI":"10.1021\/acs.orglett.5c03522","article-title":"Chemoenzymatic\nDecarboxylative Bromination of Acetylenic Acids Using Vanadium-Dependent\nChloroperoxidase","volume":"27","author":"Zeng","year":"2025","journal-title":"Org. Lett."},{"issue":"7","key":"2026102111083247700_cit50","doi-asserted-by":"publisher","first-page":"4622","DOI":"10.1021\/acscatal.2c05531","article-title":"Decarboxylative\nBromooxidation of Indoles by a Vanadium Haloperoxidase","volume":"13","author":"Wells","year":"2023","journal-title":"ACS Catal."},{"issue":"50","key":"2026102111083247700_cit51","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202411387","article-title":"N-Halogenation\nby Vanadium-Dependent Haloperoxidases Enables 1,2,4-Oxadiazole Synthesis","volume":"63","author":"Sharma","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"issue":"12","key":"2026102111083247700_cit52","doi-asserted-by":"publisher","first-page":"10698","DOI":"10.1021\/jacs.5c01175","article-title":"Intermolecular 1,2,4-Thiadiazole Synthesis Enabled\nby Enzymatic Halide Recycling with Vanadium-Dependent Haloperoxidases","volume":"147","author":"Sharma","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"2","key":"2026102111083247700_cit53","doi-asserted-by":"publisher","first-page":"2491","DOI":"10.1021\/jacs.5c17554","article-title":"Chemoenzymatic Diazo Synthesis Enabled\nby Enzymatic Halide Recycling with Vanadium-Dependent Haloperoxidases","volume":"148","author":"Sharma","year":"2026","journal-title":"J. Am. Chem. Soc."},{"issue":"16","key":"2026102111083247700_cit54","doi-asserted-by":"publisher","first-page":"5108","DOI":"10.1021\/acs.orglett.6c00937","article-title":"Chemoenzymatic Triazolopyridine Synthesis Enabled by\nCryptic Diazo Formation by Vanadium-Dependent Haloperoxidases","volume":"28","author":"Sharma","year":"2026","journal-title":"Org. 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Soc."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c16767","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/41\/45103\/68796593\/jacs.6c16767.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/41\/45103\/68796593\/jacs.6c16767.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,21]],"date-time":"2026-10-21T15:31:24Z","timestamp":1792596684000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/41\/45103\/5447586\/A-Substrate-Permissive-Vanadium-Haloperoxidase-in"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,9]]},"references-count":56,"journal-issue":{"issue":"41","published-online":{"date-parts":[[2026,10,9]]},"published-print":{"date-parts":[[2026,10,21]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c16767","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,9]]}}}