{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T07:19:00Z","timestamp":1791875940076,"version":"4.3.4"},"reference-count":61,"publisher":"Wiley","issue":"50","license":[{"start":{"date-parts":[[2024,10,30]],"date-time":"2024-10-30T00:00:00Z","timestamp":1730246400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100006939","name":"Emory University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100006939","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100007482","name":"Arizona State University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007482","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2024,12,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Nitrogen\u2010containing compounds are valuable synthetic intermediates and targets in nearly every chemical industry. While methods for nitrogen\u2010carbon and nitrogen\u2010heteroatom bond formation have primarily relied on nucleophilic nitrogen atom reactivity, molecules containing nitrogen\u2010halogen bonds allow for electrophilic or radical reactivity modes at the nitrogen center. Despite the growing synthetic utility of nitrogen\u2010halogen bond\u2010containing compounds, selective catalytic strategies for their synthesis are largely underexplored. We recently discovered that the vanadium\u2010dependent haloperoxidase (VHPO) class of enzymes are a suitable biocatalyst platform for nitrogen\u2010halogen bond formation. Herein, we show that VHPOs perform selective halogenation of a range of substituted benzamidine hydrochlorides to produce the corresponding N\u2019\u2010halobenzimidamides. This biocatalytic platform is applied to the synthesis of 1,2,4\u2010oxadiazoles from the corresponding N\u2010acylbenzamidines in high yield and with excellent chemoselectivity. Finally, the synthetic applicability of this biotechnology is demonstrated in an extension to nitrogen\u2010nitrogen bond formation and the chemoenzymatic synthesis of the Duchenne muscular dystrophy drug, ataluren.<\/jats:p>","DOI":"10.1002\/anie.202411387","type":"journal-article","created":{"date-parts":[[2024,8,25]],"date-time":"2024-08-25T23:28:09Z","timestamp":1724628489000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["N\u2010Halogenation by Vanadium\u2010Dependent Haloperoxidases Enables 1,2,4\u2010Oxadiazole Synthesis"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1951-4274","authenticated-orcid":false,"given":"Manik","family":"Sharma","sequence":"first","affiliation":[{"name":"Department of Chemistry Emory University  1515 Dickey Dr Atlanta GA 30322"},{"name":"School of Molecular Sciences Arizona State University  551 E University Dr Tempe AZ 85281"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0282-396X","authenticated-orcid":false,"given":"Zoe E.","family":"Patton","sequence":"additional","affiliation":[{"name":"Department of Chemistry Emory University  1515 Dickey Dr Atlanta GA 30322"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carlie R.","family":"Shoemaker","sequence":"additional","affiliation":[{"name":"School of Molecular Sciences Arizona State University  551 E University Dr Tempe AZ 85281"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5681-4458","authenticated-orcid":false,"given":"John","family":"Bacsa","sequence":"additional","affiliation":[{"name":"Department of Chemistry Emory University  1515 Dickey Dr Atlanta GA 30322"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1905-1919","authenticated-orcid":false,"given":"Kyle F.","family":"Biegasiewicz","sequence":"additional","affiliation":[{"name":"Department of Chemistry Emory University  1515 Dickey Dr Atlanta GA 30322"},{"name":"School of Molecular Sciences Arizona State University  551 E University Dr Tempe AZ 85281"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,10,30]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25081909"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA09198G"},{"key":"e_1_2_3_4_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/ps.3615"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2021.116162"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1055\/a-2142-8961"},{"key":"e_1_2_3_8_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA14525F"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26216579"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.mcat.2021.111517"},{"key":"e_1_2_3_12_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB03091J"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00462"},{"key":"e_1_2_3_15_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00383"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00286C"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00248"},{"key":"e_1_2_3_19_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00512"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2022.214667"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.esci.2022.11.002"},{"key":"e_1_2_3_23_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202102864"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00831"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00444"},{"key":"e_1_2_3_27_1","unstructured":"For recent reviews see:"},{"key":"e_1_2_3_28_2","first-page":"1","volume":"46","author":"Bell E. 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