{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T03:58:37Z","timestamp":1785470317765,"version":"3.56.0"},"reference-count":48,"publisher":"American Chemical Society (ACS)","issue":"23","license":[{"start":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T00:00:00Z","timestamp":1780358400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T00:00:00Z","timestamp":1780358400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T00:00:00Z","timestamp":1780358400000},"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":["22101236"],"award-info":[{"award-number":["22101236"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005892","name":"China Academy of Chinese Medical Sciences","doi-asserted-by":"publisher","award":["CI2024C004YN"],"award-info":[{"award-number":["CI2024C004YN"]}],"id":[{"id":"10.13039\/501100005892","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Key Project at Central Government Level The Ability Establishment of Sustainable Use for Valuable Chinese Medicine Resources","doi-asserted-by":"publisher","award":["2060302"],"award-info":[{"award-number":["2060302"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Science and Technology Innovation Key Research and Development Program of Chongqing","doi-asserted-by":"publisher","award":["CSTB2022TIAD-STX0015"],"award-info":[{"award-number":["CSTB2022TIAD-STX0015"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Fundamental Research Funds for the Central Public Welfare Research Institutes","doi-asserted-by":"publisher","award":["ZZ16-YQ-042"],"award-info":[{"award-number":["ZZ16-YQ-042"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,6,17]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The asymmetric construction of highly congested polycyclic architectures remains a formidable challenge in chemical synthesis. Biocatalysis offers exquisite stereocontrol, yet the repertoire of enzyme-catalyzed cycloadditions remains notably limited. Here, we elucidate the intriguing oxidative [3 + 2] cycloaddition capability of a flavoenzyme CpaO and develop it as a robust biocatalyst for asymmetric construction of the pentacyclic scaffold of (\u2212)-\u03b1-Cyclopiazonic acid ((\u2212)-\u03b1-CPA), a nanomolar inhibitor of sarco\/endoplasmic reticulum calcium(II)-dependent ATPase. This work presents not only the most concise, scalable, and fully asymmetric synthesis of (\u2212)-\u03b1-CPA to date but also unlocks the collective access to its highly oxidized, structurally diverse family members, thereby enriching the scenarios of enzyme-catalyzed bonding strategies in natural product synthesis.<\/jats:p>","DOI":"10.1021\/jacs.6c05047","type":"journal-article","created":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T06:57:52Z","timestamp":1780383472000},"page":"24221-24229","source":"Crossref","is-referenced-by-count":0,"title":["Biocatalytic Oxidative\n[3 + 2] Cycloaddition Enables\nDivergent Synthesis of (\u2212)-\u03b1-Cyclopiazonic Acid and Derived\nAlkaloids"],"prefix":"10.1021","volume":"148","author":[{"given":"Zeping","family":"Wang","sequence":"first","affiliation":[{"name":"Southwest University , , ,","place":["Chongqing, China, 400715"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Delin","family":"Tang","sequence":"additional","affiliation":[{"name":"Southwest University , , ,","place":["Chongqing, China, 400715"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haibo","family":"Feng","sequence":"additional","affiliation":[{"name":"Southwest University , , ,","place":["Chongqing, China, 400715"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rui","family":"Tong","sequence":"additional","affiliation":[{"name":"Southwest University , , ,","place":["Chongqing, China, 400715"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mengfei","family":"Long","sequence":"additional","affiliation":[{"name":"Southwest University , , ,","place":["Chongqing, China, 400715"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Meng","family":"Xia","sequence":"additional","affiliation":[{"name":"Chinese Academy of Chinese Medical Sciences , , ,","place":["Beijing, China, 100700"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yang","family":"Han","sequence":"additional","affiliation":[{"name":"Chinese Academy of Chinese Medical Sciences , , ,","place":["Beijing, China, 100700"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2070-4318","authenticated-orcid":true,"given":"Luqi","family":"Huang","sequence":"additional","affiliation":[{"name":"Chinese Academy of Chinese Medical Sciences , , ,","place":["Beijing, China, 100700"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5187-4889","authenticated-orcid":true,"given":"Ping","family":"Su","sequence":"additional","affiliation":[{"name":"Chinese Academy of Chinese Medical Sciences , , ,","place":["Beijing, China, 100700"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4331-2285","authenticated-orcid":true,"given":"Xiao","family":"Zhang","sequence":"additional","affiliation":[{"name":"Southwest University , , ,","place":["Chongqing, China, 400715"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,6,2]]},"reference":[{"key":"2026073023094486200_cit1","doi-asserted-by":"publisher","first-page":"2101","DOI":"10.1016\/0040-4020(68)88113-X","article-title":"The isolation\nand structure of cyclopiazonic acid, a toxic metabolite of penicillium cyclopium westling","volume":"24","author":"Holzapfel","year":"1968","journal-title":"Tetrahedron"},{"key":"2026073023094486200_cit2","doi-asserted-by":"publisher","first-page":"261","DOI":"10.1016\/0041-008X(92)90076-5","article-title":"Comparison of three\ntetramic acids and their ability to alter membrane function in cultured\nskeletal muscle cells and sarcoplasmic reticulum vesicles","volume":"114","author":"Riley","year":"1992","journal-title":"Toxicol. 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X.; Yan, Y.; Hisao, P.-Y.; Chang, C.-Y.; Wang, N.\n          A single flavoenzyme forges the pentacyclic skeleton\nof \u03b1-cyclopiazonic acid."},{"key":"2026073023094486200_cit30","doi-asserted-by":"publisher","first-page":"176","DOI":"10.1016\/j.fgb.2008.11.002","article-title":"Clustered genes involved in cyclopiazonic\nacid production are next to the aflatoxin biosynthesis gene cluster\nin Aspergillus flavus","volume":"46","author":"Chang","year":"2009","journal-title":"Fungal\nGenet. 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Syst."},{"key":"2026073023094486200_cit43","doi-asserted-by":"publisher","first-page":"2910","DOI":"10.1021\/jo1001388","article-title":"Synthesis\nof unnatural selenocystines and beta-aminodiselenides via regioselective\nring-opening of sulfamidates using a sequential, one-pot, multistep\nstrategy","volume":"75","author":"Baig","year":"2010","journal-title":"J. Org. Chem."},{"key":"2026073023094486200_cit44","doi-asserted-by":"publisher","first-page":"10769","DOI":"10.1021\/jacs.7b05007","article-title":"Unlocking\nreactivity of TrpB: A general biocatalytic platform for synthesis\nof tryptophan analogues","volume":"139","author":"Romney","year":"2017","journal-title":"J. Am. Chem. 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Front."},{"key":"2026073023094486200_cit48","doi-asserted-by":"publisher","first-page":"403","DOI":"10.1021\/acs.biochem.7b00998","article-title":"Applications of oxygenases\nin the chemoenzymatic total synthesis of complex natural products","volume":"57","author":"King-Smith","year":"2018","journal-title":"Biochemistry"}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c05047","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/23\/24221\/66271334\/jacs.6c05047.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/23\/24221\/66271334\/jacs.6c05047.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T03:09:51Z","timestamp":1785467391000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/23\/24221\/5233448\/Biocatalytic-Oxidative-3-2-Cycloaddition-Enables"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,6,2]]},"references-count":48,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2026,6,2]]},"published-print":{"date-parts":[[2026,6,17]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c05047","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,6,2]]}}}