{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T19:46:49Z","timestamp":1792784809015,"version":"4.5.0"},"reference-count":27,"publisher":"American Chemical Society (ACS)","issue":"36","license":[{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100017369","name":"Scientific and Technological Planning Project of Guangzhou City","doi-asserted-by":"publisher","award":["2025A04J4623"],"award-info":[{"award-number":["2025A04J4623"]}],"id":[{"id":"10.13039\/100017369","id-type":"DOI","asserted-by":"publisher"}]},{"name":"National Basic Research Program of China (973 Program)","award":["2023YFA0914200"],"award-info":[{"award-number":["2023YFA0914200"]}]},{"name":"Key Science and Technology Plan Projects in Nansha District","award":["2023ZD010"],"award-info":[{"award-number":["2023ZD010"]}]},{"name":"National Natural Science Foundation of China (NSFC)","award":["22177116"],"award-info":[{"award-number":["22177116"]}],"id":[{"id":"https:\/\/ror.org\/01h0zpd94","id-type":"ROR","asserted-by":"crossref"}]},{"name":"National Natural Science Foundation of China (NSFC)","award":["22267006"],"award-info":[{"award-number":["22267006"]}],"id":[{"id":"https:\/\/ror.org\/01h0zpd94","id-type":"ROR","asserted-by":"crossref"}]},{"name":"National Natural Science Foundation of China (NSFC)","award":["22477125"],"award-info":[{"award-number":["22477125"]}],"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":[[2026,9,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Organic carbonates (OCs) have a wide range of applications across materials science, synthetic chemistry, and medicine. The development of efficient catalytic processes for converting carbon dioxide (CO2) into OCs represents a crucial objective in sustainable chemistry and energy research. Among available strategies, the coupling of CO2 with epoxides to form cyclic carbonates is one of the most technologically and economically promising routes for CO2 valorization. Although considerable progress has been made in designing high-performance catalysts for this transformation, several limitations remain, including dependence on organic solvents, transition metal-based catalytic systems, and energy-intensive conditions, typically involving elevated temperatures and high CO2 pressures. While an increasing number of naturally occurring OCs have been identified, the biosynthetic mechanisms underlying their formation, especially for fungal-derived five-membered cyclic carbonates, remain largely unknown. In this study, we identified and functionally characterized all enzymes involved in cytosporin biosynthesis and elucidated the complete biosynthetic pathway. We demonstrated that the five-membered cyclic carbonate moiety in cytosporin E arises through a nonenzymatic, epoxide-mediated CO2 coupling reaction under neutral aqueous conditions. This strategy for constructing a five-membered cyclic carbonate is unprecedented in natural product biosynthesis and may offer valuable insights for developing environmentally benign synthetic routes toward OCs.<\/jats:p>","DOI":"10.1021\/jacs.6c12612","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T09:14:54Z","timestamp":1788426894000},"page":"39121-39127","source":"Crossref","is-referenced-by-count":1,"title":["Epoxide-Mediated Carbon\nDioxide Coupling Yields the\nFive-Membered Cyclic Carbonate in Cytosporin Biosynthesis"],"prefix":"10.1021","volume":"148","author":[{"given":"Hua","family":"Xiao","sequence":"first","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"Sanya Institute of Oceanology Eco-Environmental Engineering , Yazhou Scientific Bay , ,","place":["Sanya, China, 572000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yong","family":"He","sequence":"additional","affiliation":[{"name":"Hainan Normal University , , ,","place":["Haikou, China, 571158"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiufeng","family":"Zhang","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"Sanya Institute of Oceanology Eco-Environmental Engineering , Yazhou Scientific Bay , ,","place":["Sanya, China, 572000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chenran","family":"Xu","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"University of Chinese Academy of Sciences , 19 Yuquan Road , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8619-7566","authenticated-orcid":true,"given":"Yongxiang","family":"Song","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"University of Chinese Academy of Sciences , 19 Yuquan Road , ,","place":["Beijing, China, 100049"]},{"name":"Sanya Institute of Oceanology Eco-Environmental Engineering , Yazhou Scientific Bay , ,","place":["Sanya, China, 572000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Menglan","family":"Luo","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"University of Chinese Academy of Sciences , 19 Yuquan Road , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanqin","family":"Li","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"Sanya Institute of Oceanology Eco-Environmental Engineering , Yazhou Scientific Bay , ,","place":["Sanya, China, 572000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huijuan","family":"Li","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"University of Chinese Academy of Sciences , 19 Yuquan Road , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xianglong","family":"Zhu","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"University of Chinese Academy of Sciences , 19 Yuquan Road , ,","place":["Beijing, China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jian","family":"Cai","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4386-0572","authenticated-orcid":true,"given":"Wan-Shan","family":"Li","sequence":"additional","affiliation":[{"name":"Hainan Normal University , , ,","place":["Haikou, China, 571158"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6073-9921","authenticated-orcid":true,"given":"Yan","family":"Yan","sequence":"additional","affiliation":[{"name":"South China Sea Institute of Oceanology, Chinese Academy of Sciences , , 164 West Xingang Road , ,","place":["Guangzhou, China, 510301"]},{"name":"University of Chinese Academy of Sciences , 19 Yuquan Road , ,","place":["Beijing, China, 100049"]},{"name":"Sanya Institute of Oceanology Eco-Environmental Engineering , Yazhou Scientific Bay , ,","place":["Sanya, China, 572000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,1]]},"reference":[{"key":"2026091609112519200_cit1","doi-asserted-by":"publisher","first-page":"1312","DOI":"10.1039\/b819997c","article-title":"The synthesis of organic\ncarbonates from carbon dioxide","volume":"11","author":"Sakakura","year":"2009","journal-title":"Chem. Commun."},{"issue":"3","key":"2026091609112519200_cit2","doi-asserted-by":"publisher","first-page":"951","DOI":"10.1021\/cr950067i","article-title":"Organic carbonates","volume":"96","author":"Shaikh","year":"1996","journal-title":"Chem. Rev."},{"issue":"8","key":"2026091609112519200_cit3","doi-asserted-by":"publisher","first-page":"4554","DOI":"10.1021\/cr900393d","article-title":"Organic carbonates\nas solvents in synthesis and catalysis","volume":"110","author":"Scha\u0308ffner","year":"2010","journal-title":"Chem.\nRev."},{"issue":"42","key":"2026091609112519200_cit4","doi-asserted-by":"publisher","first-page":"8207","DOI":"10.1016\/S0040-4020(00)00671-2","article-title":"Perspectives on alkyl carbonates\nin organic synthesis","volume":"56","author":"Parrish","year":"2000","journal-title":"Tetrahedron"},{"issue":"4","key":"2026091609112519200_cit5","doi-asserted-by":"publisher","first-page":"1462","DOI":"10.1039\/C1CS15142H","article-title":"Cobalt\ncatalysts for the coupling of CO2 and epoxides to provide\npolycarbonates and cyclic carbonates","volume":"41","author":"Lu","year":"2012","journal-title":"Chem.\nSoc. Rev."},{"key":"2026091609112519200_cit6","first-page":"87","article-title":"Aldgamycin E a new neutral macrolide\nantibiotic","volume":"10","author":"Kunstmann","year":"1965","journal-title":"Antimicrob. Agents Chemother."},{"issue":"2","key":"2026091609112519200_cit7","doi-asserted-by":"publisher","first-page":"68","DOI":"10.11554\/antibioticsa.18.2_68","article-title":"Neocarzinostatin, an\nantitumor antibiotic of high molecular weight isolation, physicochemical\nproperties and biological activities","volume":"18","author":"Ishida","year":"1965","journal-title":"J. Antibiot."},{"issue":"39","key":"2026091609112519200_cit8","doi-asserted-by":"publisher","first-page":"7047","DOI":"10.1016\/j.tetlet.2006.07.099","article-title":"The first example of\nnatural cyclic carbonate in terpenoids","volume":"47","author":"Rosselli","year":"2006","journal-title":"Tetrahedron\nLett."},{"issue":"2","key":"2026091609112519200_cit9","doi-asserted-by":"publisher","first-page":"188","DOI":"10.1590\/S0100-40422004000200003","article-title":"Lignanas de Strychnos\nguianensis (Aublet) Mart","volume":"27","author":"Pinheiro","year":"2004","journal-title":"Quim. 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B"},{"issue":"2","key":"2026091609112519200_cit15","doi-asserted-by":"publisher","first-page":"119","DOI":"10.7164\/antibiotics.49.119","article-title":"Discovery of an angiotensin\nII binding inhibitor from\na Cytospora sp. using semi-automated screening procedures","volume":"49","author":"Stevens-Miles","year":"1996","journal-title":"J. Antibiot."},{"issue":"7","key":"2026091609112519200_cit16","doi-asserted-by":"publisher","first-page":"382","DOI":"10.3390\/md21070382","article-title":"Cytosporin\nderivatives from arctic-derived\nfungus Eutypella sp. D-1 via the OSMAC approach","volume":"21","author":"Yu","year":"2023","journal-title":"Mar. Drugs"},{"issue":"7","key":"2026091609112519200_cit17","doi-asserted-by":"publisher","first-page":"552","DOI":"10.1038\/nchembio.1527","article-title":"A carbonate-forming Baeyer-Villiger\nmonooxygenase","volume":"10","author":"Hu","year":"2014","journal-title":"Nat. Chem. Biol."},{"issue":"50","key":"2026091609112519200_cit18","doi-asserted-by":"publisher","first-page":"19538","DOI":"10.1021\/jacs.9b09669","article-title":"Fungal highly\nreducing polyketide\nsynthases biosynthesize salicylaldehydes that are precursors to epoxycyclohexenol\nnatural products","volume":"141","author":"Liu","year":"2019","journal-title":"J. Am. Chem. Soc."},{"issue":"6","key":"2026091609112519200_cit19","doi-asserted-by":"publisher","first-page":"2256","DOI":"10.1021\/acs.orglett.0c00440","article-title":"Biosynthesis of\nthe prenylated salicylaldehyde flavoglaucin requires temporary reduction\nto salicyl alcohol for decoration before reoxidation to the final\nproduct","volume":"22","author":"Nies","year":"2020","journal-title":"Org. Lett."},{"issue":"13","key":"2026091609112519200_cit20","doi-asserted-by":"publisher","first-page":"3560","DOI":"10.1021\/acs.orglett.7b01534","article-title":"Identification\nand heterologous production\nof a benzoyl-primed tricarboxylic acid polyketide intermediate from\nthe zaragozic acid A biosynthetic pathway","volume":"19","author":"Liu","year":"2017","journal-title":"Org.\nLett."},{"issue":"20","key":"2026091609112519200_cit21","doi-asserted-by":"publisher","first-page":"11293","DOI":"10.1021\/jacs.3c02011","article-title":"Ketoreductase domain-catalyzed\npolyketide\nchain release in fungal alkyl salicylaldehyde biosynthesis","volume":"145","author":"Yang","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"14","key":"2026091609112519200_cit22","doi-asserted-by":"publisher","first-page":"10796","DOI":"10.1021\/acscatal.4c01043","article-title":"Structural and computational\ninsights\ninto the noncanonical aromatization in fungal polyketide biosynthesis","volume":"14","author":"Wang","year":"2024","journal-title":"ACS Catal."},{"issue":"32","key":"2026091609112519200_cit23","doi-asserted-by":"publisher","first-page":"29582","DOI":"10.1021\/jacs.5c10778","article-title":"Epoxide\nstereochemistry controls regioselective ketoreduction in epoxyquinoid\nbiosynthesis","volume":"147","author":"Wang","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"7714","key":"2026091609112519200_cit24","doi-asserted-by":"publisher","first-page":"415","DOI":"10.1038\/s41586-018-0319-4","article-title":"Resistance-gene-directed discovery of a natural-product herbicide\nwith a new mode of action","volume":"559","author":"Yan","year":"2018","journal-title":"Nature"},{"issue":"1","key":"2026091609112519200_cit25","doi-asserted-by":"publisher","first-page":"374","DOI":"10.1021\/ja00521a063","article-title":"Structural\ndependence of oxygen-18 isotope shifts in carbon-13 NMR spectra","volume":"102","author":"Vederas","year":"1980","journal-title":"J. Am. Chem. Soc."},{"issue":"3","key":"2026091609112519200_cit26","doi-asserted-by":"publisher","first-page":"1709","DOI":"10.1021\/cr4002758","article-title":"Catalysis for the valorization of\nexhaust carbon: from CO2 to chemicals, materials, and fuels.\nTechnological use of CO2","volume":"114","author":"Aresta","year":"2014","journal-title":"Chem. Rev."},{"issue":"51","key":"2026091609112519200_cit27","doi-asserted-by":"publisher","first-page":"9822","DOI":"10.1002\/anie.201002087","article-title":"Salen-complex-mediated\nformation\nof cyclic carbonates by cycloaddition of CO2 to epoxides","volume":"49","author":"Decortes","year":"2010","journal-title":"Angew. Chem. Int. Ed."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c12612","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/36\/39121\/68084991\/jacs.6c12612.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/36\/39121\/68084991\/jacs.6c12612.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T13:32:02Z","timestamp":1789565522000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/36\/39121\/5394056\/Epoxide-Mediated-Carbon-Dioxide-Coupling-Yields"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,1]]},"references-count":27,"journal-issue":{"issue":"36","published-online":{"date-parts":[[2026,9,1]]},"published-print":{"date-parts":[[2026,9,16]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c12612","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,1]]}}}