{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"institution":[{"name":"bioRxiv"}],"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T21:19:06Z","timestamp":1792790346374,"version":"4.5.0"},"posted":{"date-parts":[[2026,8,12]]},"group-title":"Biochemistry","reference-count":64,"publisher":"openRxiv","license":[{"start":{"date-parts":[[2026,8,12]],"date-time":"2026-08-12T00:00:00Z","timestamp":1786492800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Institutes of Health","award":["R35GM147387"],"award-info":[{"award-number":["R35GM147387"]}]},{"name":"National Science Foundation","award":["CHE-2400087"],"award-info":[{"award-number":["CHE-2400087"]}]},{"name":"Alfred P. 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Herein, we report a photometallobiocatalytic enantioselective intermolecular C\u2013C cross-coupling of pyridotriazoles and secondary alkyltrifluoroborate salts through cooperative catalysis between an organic photosensitizer and an engineered protoglobin. By combining visible-light-mediated radical generation with enzymatic activation of pyridotriazoles to form reactive Fe carbenoid intermediates, this transformation enabled highly enantioselective radical C\u2013C bond formation through a proposed outer-sphere coupling mechanism. Through biocatalyst mining and directed evolution, engineered Aeropyrum pernix protoglobin catalysts were developed that catalyzed this radical C\u2013C coupling with excellent efficiency and stereocontrol. The photobiocatalytic platform exhibited a broad substrate scope with respect to both secondary alkyltrifluoroborate salts and pyridotriazoles, affording a range of valuable N-heterocyclic products in excellent yields and enantioselectivities. Mechanistic studies supported the involvement of radical intermediates and revealed spontaneous binding between the photocatalyst eosin B and the engineered metalloenzyme. By leveraging cooperative photometallobiocatalysis, this work established an underexplored strategy for asymmetric intermolecular radical cross-coupling via an outer-sphere mechanism, further expanding the catalytic repertoire of transition-metal carbenoid chemistry.<\/jats:p>\n                <jats:sec>\n                  <jats:title>Entry for the Table of Contents<\/jats:title>\n                  <jats:fig id=\"ufig1\" position=\"float\" fig-type=\"figure\" orientation=\"portrait\">\n                    <jats:caption>\n                      <jats:p>\n                        An enantioselective photometallobiocatalytic cross-coupling of pyridotriazoles and secondary alkyltrifluoroborate salts is developed. Cooperative catalysis using eosin B and an engineered protoglobin combines visible-light-mediated radical generation with enzymatic metal carbenoid activation, affording valuable\n                        <jats:italic>N<\/jats:italic>\n                        -heterocyclic products in excellent yield and enantioselectivity through an outer-sphere radical coupling pathway.\n                      <\/jats:p>\n                    <\/jats:caption>\n                    <jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"744224v1_ufig1\" position=\"float\" orientation=\"portrait\"\/>\n                  <\/jats:fig>\n                <\/jats:sec>","DOI":"10.64898\/2026.08.11.744224","type":"posted-content","created":{"date-parts":[[2026,8,12]],"date-time":"2026-08-12T11:25:16Z","timestamp":1786533916000},"source":"Crossref","is-referenced-by-count":0,"title":["Photometallobiocatalytic Asymmetric Radical-Mediated Cross-Coupling of Organotrifluoroborate Salts and Pyridotriazoles"],"prefix":"10.64898","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9699-3358","authenticated-orcid":false,"given":"Huanan","family":"Wang","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, California 93106, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Binh Khanh","family":"Mai","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 93106, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xingjie","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, California 93106, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chongtao","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, California 93106, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peng","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 93106, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4956-2034","authenticated-orcid":false,"given":"Yang","family":"Yang","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, California 93106, USA"},{"name":"Department of Bioengineering, University of California Santa Barbara, Santa Barbara, California 93106, USA"},{"name":"Biomolecular Science and Engineering (BMSE) Program, University of California Santa Barbara, Santa Barbara, California 93106, USA"},{"name":"Howard Hughes Medical Institute, University of California Santa Barbara, Santa Barbara, California 93106, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"54368","reference":[{"key":"2026092508000625000_2026.08.11.744224v1.1","doi-asserted-by":"publisher","DOI":"10.1039\/b913880n"},{"key":"2026092508000625000_2026.08.11.744224v1.2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300503r"},{"key":"2026092508000625000_2026.08.11.744224v1.3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00057"},{"key":"2026092508000625000_2026.08.11.744224v1.4","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00018"},{"key":"2026092508000625000_2026.08.11.744224v1.5","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.1c00383"},{"key":"2026092508000625000_2026.08.11.744224v1.6","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505090"},{"key":"2026092508000625000_2026.08.11.744224v1.7","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b08856"},{"key":"2026092508000625000_2026.08.11.744224v1.8","doi-asserted-by":"publisher","DOI":"10.1038\/nature11117"},{"key":"2026092508000625000_2026.08.11.744224v1.9","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1038\/s41929-019-0385-5","article-title":"Engineering new catalytic activities in enzymes","volume":"3","year":"2020","journal-title":"Nat. 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