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These natural products have attracted considerable attention owing to their unique biological functions, including plant hormone-like properties and antiproliferative activities against cancer cells. Herein, we report the stereoselective synthesis of 6-aza-FC-type analogs via a chemoenzymatic skeletal editing approach using CotB2, a diterpene synthase responsible for constructing the FC skeleton. Based on the biosynthetic reaction mechanism, we designed an unnatural substrate bearing an amide moiety at the C6\u2013C7 position of geranylgeranyl pyrophosphate. CotB2 promoted the cyclization of this substrate to afford an optically active 5\/11-fused lactam in a stereoselective manner. Subsequent intramolecular cyclization of the resulting lactam through an epoxide intermediate furnished 6-aza-FC derivatives, in which the C6 carbon of FC skeleton is replaced with a nitrogen atom. Notably, one of the 6-aza-FC analogs exhibited selective cytotoxicity toward cancer cells, while displaying reduced activity toward HUVEC cells.<\/jats:p>","DOI":"10.1021\/jacsau.6c00833","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T13:20:59Z","timestamp":1785849659000},"page":"5207-5213","source":"Crossref","is-referenced-by-count":0,"title":["Formal Chemoenzymatic Skeletal Editing of Fusicoccane\nCore to Access 6-Aza-Fusicoccanes"],"prefix":"10.1021","volume":"6","author":[{"given":"Seiya","family":"Endo","sequence":"first","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-7691-8261","authenticated-orcid":true,"given":"Eigo","family":"Fukuda","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ken-ya","family":"Hori","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kei-ichi","family":"Murai","sequence":"additional","affiliation":[{"name":"The University of Tokyo , , 1-1-1 Yayoi , , ,","place":["Bunkyo-ku, Tokyo, Japan, 113-8657"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4072-3804","authenticated-orcid":true,"given":"Atsushi","family":"Nakayama","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi, ,","place":["Osaka, Japan, 558-8585"]},{"name":"The University of Osaka , , 1-6 Yamadaoka , , ,","place":["Suita, Osaka, Japan, 565-0871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6725-8610","authenticated-orcid":true,"given":"Yoko","family":"Yasuno","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masayoshi","family":"Arai","sequence":"additional","affiliation":[{"name":"The University of Osaka , , 1-6 Yamadaoka , , ,","place":["Suita, Osaka, Japan, 565-0871"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5185-096X","authenticated-orcid":true,"given":"Hajime","family":"Sato","sequence":"additional","affiliation":[{"name":"The University of Tokyo , , 1-1-1 Yayoi , , ,","place":["Bunkyo-ku, Tokyo, Japan, 113-8657"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomohisa","family":"Kuzuyama","sequence":"additional","affiliation":[{"name":"The University of Tokyo , , 1-1-1 Yayoi , , ,","place":["Bunkyo-ku, Tokyo, Japan, 113-8657"]},{"name":"The University of Tokyo , , 1-1-1 Yayoi , , ,","place":["Bunkyo-ku, Tokyo, Japan, 113-8657"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9145-1533","authenticated-orcid":true,"given":"Tetsuro","family":"Shinada","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,30]]},"reference":[{"key":"2026092808090169500_cit1","doi-asserted-by":"publisher","first-page":"154224","DOI":"10.1016\/j.tetlet.2022.154224","article-title":"Biosynthesis\nof fusicoccane-type diterpenoids featuring a 5\u20138\u20135 tricyclic\ncarbon skeleton","volume":"112","author":"Liu","year":"2022","journal-title":"Tetrahedron Lett."},{"issue":"6","key":"2026092808090169500_cit2","doi-asserted-by":"publisher","first-page":"360","DOI":"10.1016\/j.tplants.2012.02.007","article-title":"Fusicoccanes: Diterpenes\nwith surprising biological functions","volume":"17","author":"de Boer","year":"2012","journal-title":"Trends\nPlant Sci."},{"key":"2026092808090169500_cit3","doi-asserted-by":"publisher","first-page":"5531","DOI":"10.1093\/jxb\/erae300","article-title":"The fusicoccin story revisited","volume":"75","author":"de Boer","year":"2024","journal-title":"J. Exp. Bot."},{"key":"2026092808090169500_cit4","doi-asserted-by":"publisher","first-page":"297","DOI":"10.1038\/203297a0","article-title":"Fusicoccin: A New Wilting\nToxin produced by Fusicoccum amygdali Del","volume":"203","author":"Ballio","year":"1964","journal-title":"Nature"},{"key":"2026092808090169500_cit5","doi-asserted-by":"publisher","first-page":"1588","DOI":"10.1080\/00021369.1970.10859815","article-title":"Promotion\nof the enlargement of cotyledons by cotylenins A and B","volume":"34","author":"Sassa","year":"1970","journal-title":"Agr. Biol. Chem."},{"key":"2026092808090169500_cit6","doi-asserted-by":"publisher","first-page":"85","DOI":"10.1016\/j.tips.2025.10.013","article-title":"Molecular\nglues evolve from serendipity\nto rational design","volume":"47","author":"Shrivastav","year":"2026","journal-title":"Trends Pharmacol. Sci."},{"key":"2026092808090169500_cit7","doi-asserted-by":"publisher","first-page":"49","DOI":"10.1007\/s00425-018-3051-2","article-title":"From plant physiology\nto pharmacology: Fusicoccin leaves the leaves","volume":"249","author":"Camoni","year":"2019","journal-title":"Planta"},{"key":"2026092808090169500_cit8","doi-asserted-by":"publisher","first-page":"375","DOI":"10.1002\/pca.70054","article-title":"Natural Product Modulators of Protein-Protein\nInteractions: A Comprehensive Review","volume":"37","author":"Kamel","year":"2026","journal-title":"Phytochem.\nAnal."},{"key":"2026092808090169500_cit9","doi-asserted-by":"publisher","first-page":"2124","DOI":"10.1021\/acs.jmedchem.4c01936","article-title":"Recent Developments\nin 14\u20133-3 Stabilizers for Regulating Protein-Protein\nInteractions: An Update","volume":"68","author":"Tian","year":"2025","journal-title":"J. Med. Chem."},{"key":"2026092808090169500_cit10","doi-asserted-by":"publisher","first-page":"454","DOI":"10.1038\/s41570-025-00717-3","article-title":"The role and\nstructure of molecular glues in plant\nsignalling networks","volume":"9","author":"Lozano-Elena","year":"2025","journal-title":"Nat. Rev. Chem."},{"key":"2026092808090169500_cit11","doi-asserted-by":"publisher","first-page":"23431","DOI":"10.1038\/s41598-024-73979-4","article-title":"Fungal toxin fusicoccin\nenhances plant growth by upregulating 14\u20133-3 interaction with\nplasma membrane H+-ATPase","volume":"14","author":"Kiriyama","year":"2024","journal-title":"Sci. Rep."},{"key":"2026092808090169500_cit12","doi-asserted-by":"publisher","first-page":"573","DOI":"10.1016\/j.chembiol.2023.04.005","article-title":"IFN\u03b1 primes cancer\ncells for Fusicoccin-induced\ncell death via 14\u20133-3 PPI stabilization","volume":"30","author":"Andlovic","year":"2023","journal-title":"Cell Chem. Biol."},{"issue":"10","key":"2026092808090169500_cit13","doi-asserted-by":"publisher","first-page":"1587","DOI":"10.7164\/antibiotics.45.1587","article-title":"Cyclooctatin,\na new inhibitor of\nlysophospholipase, produced by Streptomyces melanosporofaciens MI614-43F2. Taxonomy, production, isolation, physico-chemical properties\nand biological activities","volume":"45","author":"Aoyagi","year":"1992","journal-title":"J. Antibiot."},{"key":"2026092808090169500_cit14","doi-asserted-by":"publisher","first-page":"102141","DOI":"10.1016\/j.xcrp.2024.102141","article-title":"Recent total syntheses\nof fusicoccanes","volume":"5","author":"Liu","year":"2024","journal-title":"Cell\nRep. Phys. Sci."},{"issue":"72","key":"2026092808090169500_cit15","doi-asserted-by":"publisher","first-page":"44247","DOI":"10.1039\/D0RA09198G","article-title":"Prescribed drugs containing nitrogen heterocycles:\nAn overview","volume":"10","author":"Heravi","year":"2020","journal-title":"RSC Adv."},{"key":"2026092808090169500_cit16","doi-asserted-by":"publisher","first-page":"11622","DOI":"10.1021\/acs.jmedchem.4c01122","article-title":"An Update\non the Nitrogen Heterocycle Compositions and Properties of U.S. FDA-Approved\nPharmaceuticals (2013\u20132023)","volume":"67","author":"Marshall","year":"2024","journal-title":"J. Med.\nChem."},{"key":"2026092808090169500_cit17","doi-asserted-by":"publisher","first-page":"470","DOI":"10.1126\/science.aeh2468","article-title":"From alchemy\nto precision skeletal editing","volume":"392","author":"Wu","year":"2026","journal-title":"Science"},{"key":"2026092808090169500_cit18","doi-asserted-by":"publisher","first-page":"1633","DOI":"10.1039\/D4QO02157F","article-title":"Remodelling molecular\nframeworks via atom-level surgery: Recent advances in skeletal editing\nof (hetero)cycles","volume":"12","author":"Sharma","year":"2025","journal-title":"Org. Chem. Front."},{"key":"2026092808090169500_cit19","doi-asserted-by":"publisher","first-page":"6752","DOI":"10.1021\/jm901241e","article-title":"Escape from\nflatland: Increasing\nsaturation as an approach to improving clinical success","volume":"52","author":"Lovering","year":"2009","journal-title":"J. Med. Chem."},{"key":"2026092808090169500_cit20","doi-asserted-by":"publisher","first-page":"515","DOI":"10.1039\/c2md20347b","article-title":"Escape from\nFlatland 2: Complexity and promiscuity","volume":"4","author":"Lovering","year":"2013","journal-title":"Med.\nChem. Commun."},{"key":"2026092808090169500_cit21","unstructured":"CHEMnetBASE.\n          \n          Dictionary of Natural Products; CRC Press,\nTaylor & Francis Group, an Informa\nGroup company. https:\/\/dnp.chemnetbase.com (accessed 04 March 2026)."},{"issue":"4","key":"2026092808090169500_cit22","doi-asserted-by":"publisher","first-page":"443","DOI":"10.1002\/cjoc.202400697","article-title":"Recent advances of\nterpenoids with intriguing chemical skeletons and biological activities","volume":"43","author":"Zang","year":"2025","journal-title":"Chin. J. Chem."},{"key":"2026092808090169500_cit23","doi-asserted-by":"publisher","first-page":"1729","DOI":"10.1021\/acschembio.5b00145","article-title":"Formation of a Novel\nMacrocyclic Alkaloid from the Unnatural Farnesyl Diphosphate Analogue\nAnilinogeranyl Diphosphate by 5-Epi-Aristolochene Synthase","volume":"10","author":"Rising","year":"2015","journal-title":"ACS Chem. Biol."},{"key":"2026092808090169500_cit24","doi-asserted-by":"publisher","first-page":"11802","DOI":"10.1002\/anie.201805526","article-title":"Exploiting the synthetic potential\nof sesquiterpene cyclases for generating unnatural terpenoids","volume":"57","author":"Oberhauser","year":"2018","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026092808090169500_cit25","doi-asserted-by":"publisher","first-page":"1834","DOI":"10.1002\/cbic.201800218","article-title":"Sesquiterpene\nsynthase-catalysed formation of a new medium-sized cyclic terpenoid\nether from farnesyl diphosphate analogues","volume":"19","author":"Huynh","year":"2018","journal-title":"ChemBioChem"},{"key":"2026092808090169500_cit26","doi-asserted-by":"publisher","first-page":"3162","DOI":"10.1021\/acs.orglett.1c00882","article-title":"Mechanistic\nsimilarities of sesquiterpene\ncyclases PenA, Omp6\/7, and BcBOT2 are unraveled by an unnatural \u201cFPP-ether\u201d\nderivative","volume":"23","author":"Harms","year":"2021","journal-title":"Org. Lett."},{"key":"2026092808090169500_cit27","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.202200211","article-title":"Heterocyclic\nand alkyne terpenoids by terpene synthase mediated biotransformation\nof non-natural prenyl diphosphates: Access to new fragrances and probes","volume":"23","author":"Weigel","year":"2022","journal-title":"ChemBioChem"},{"key":"2026092808090169500_cit28","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202117273","article-title":"Mechanism of the Bifunctional Multiple\nProduct Sesterterpene Synthase AcAS from Aspergillus calidoustus","volume":"61","author":"Quan","year":"2022","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026092808090169500_cit29","doi-asserted-by":"publisher","first-page":"5888","DOI":"10.1021\/acs.orglett.4c01670","article-title":"Telescoping\na prenyltransferase and a diterpene synthase to transform unnatural\nFPP derivatives to diterpenoids","volume":"26","author":"Struwe","year":"2024","journal-title":"Org. Lett."},{"key":"2026092808090169500_cit30","doi-asserted-by":"publisher","first-page":"498","DOI":"10.1021\/acs.biochem.4c00589","article-title":"Chemoenzymatic\nformation of oxa-terpenoids by sesqui-\nand diterpene synthase-mediated biotransformations with 9-oxy-FPP\nether derivatives","volume":"64","author":"Struwe","year":"2025","journal-title":"Biochemistry"},{"key":"2026092808090169500_cit31","doi-asserted-by":"publisher","first-page":"6796","DOI":"10.1021\/acscatal.5c00272","article-title":"Expanding\nthe \u201cterpenome\u201d: Diterpene synthases accept GGPP-ether\nsubstrates","volume":"15","author":"Ravkina","year":"2025","journal-title":"ACS Catal."},{"key":"2026092808090169500_cit32","doi-asserted-by":"publisher","first-page":"1653","DOI":"10.1021\/acs.jnatprod.5c00409","article-title":"Chemoenzymatic\ngeneration of thio-analogues of \u03b4-cadinene, \u03b4-cadinol,\nand a thio-diquinane using 8-thio-farnesylpyrophosphate","volume":"88","author":"Ja\u0308ger","year":"2025","journal-title":"J. Nat. Prod."},{"issue":"5","key":"2026092808090169500_cit33","doi-asserted-by":"publisher","first-page":"5496","DOI":"10.1021\/jacs.5c19651","article-title":"Introducing\nsmall rings into farnesyl pyrophosphates paves the way for the enzymatic\ngeneration of unnatural sesquiterpene scaffolds","volume":"148","author":"Taser","year":"2026","journal-title":"J. Am. Chem. Soc."},{"key":"2026092808090169500_cit34","doi-asserted-by":"publisher","first-page":"736","DOI":"10.1016\/j.chembiol.2009.06.007","article-title":"Cloning and heterologous expression\nof the cyclooctatin biosynthetic gene cluster afford a diterpene cyclase\nand two P450 hydroxylases","volume":"16","author":"Kim","year":"2009","journal-title":"Chem. Biol."},{"key":"2026092808090169500_cit35","doi-asserted-by":"publisher","first-page":"1621","DOI":"10.1021\/acschembio.7b00154","article-title":"Structural insights\ninto the CotB2-catalyzed cyclization of geranylgeranyl diphosphate\nto the diterpene cyclooctat-9-en-7-ol","volume":"12","author":"Tomita","year":"2017","journal-title":"ACS Chem.\nBiol."},{"key":"2026092808090169500_cit36","doi-asserted-by":"publisher","first-page":"1528","DOI":"10.1107\/S1399004714005513","article-title":"The first structure of a bacterial diterpene cyclase: CotB2","volume":"D70","author":"Janke","year":"2014","journal-title":"Acta Crystallogr."},{"key":"2026092808090169500_cit37","doi-asserted-by":"publisher","first-page":"10273","DOI":"10.1039\/C5OB01785H","article-title":"The energetic viability of an unexpected\nskeletal rearrangement\nin cyclooctatin biosynthesis","volume":"13","author":"Hong","year":"2015","journal-title":"Org. Biomol. Chem."},{"key":"2026092808090169500_cit38","doi-asserted-by":"publisher","first-page":"18471","DOI":"10.1038\/srep18471","article-title":"\u201cCation-stitching\ncascade\u201d: Exquisite control of terpene cyclization in cyclooctatin\nbiosynthesis","volume":"5","author":"Sato","year":"2016","journal-title":"Sci. Rep."},{"key":"2026092808090169500_cit39","doi-asserted-by":"publisher","first-page":"3971","DOI":"10.1038\/s41467-018-06325-8","article-title":"Towards a comprehensive understanding of the structural dynamics\nof a bacterial diterpene synthase during catalysis","volume":"9","author":"Driller","year":"2018","journal-title":"Nat. Commun."},{"key":"2026092808090169500_cit40","doi-asserted-by":"publisher","first-page":"7479","DOI":"10.1021\/jo0349328","article-title":"Studies on the synthesis\nof (2S, 3R)-3-hydroxy-3-methylproline\nvia C2\u2013N bond formation","volume":"68","author":"Shen","year":"2003","journal-title":"J.\nOrg. Chem."},{"key":"2026092808090169500_cit41","doi-asserted-by":"publisher","first-page":"7439","DOI":"10.1016\/S0040-4039(98)01631-1","article-title":"A method for removal\nof N-BOC protecting groups from substrates on TFA-sensitive\nresins","volume":"39","author":"Zhang","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"2026092808090169500_cit42","doi-asserted-by":"publisher","first-page":"870","DOI":"10.1021\/jo00290a015","article-title":"Syntheses and reactions\nof silyl carbamates. 1. Chemoselective\ntransformation of amino protecting groups via tert-butyldimethylsilyl carbamates","volume":"55","author":"Sakaitani","year":"1990","journal-title":"J. Org. Chem."},{"key":"2026092808090169500_cit43","doi-asserted-by":"publisher","first-page":"2437","DOI":"10.1016\/j.bmc.2017.02.066","article-title":"Bishomoisoprenoid\ntriazole bisphosphonates as inhibitors\nof geranylgeranyl diphosphate synthase","volume":"25","author":"Wills","year":"2017","journal-title":"Bioorg.\nMed. Chem."},{"key":"2026092808090169500_cit44","doi-asserted-by":"publisher","first-page":"2015","DOI":"10.1021\/acs.orglett.8b00560","article-title":"An Isolable and Bench-Stable Epoxidizing\nReagent Based on Triazine: Triazox","volume":"20","author":"Yamada","year":"2018","journal-title":"Org. Lett."},{"key":"2026092808090169500_cit45","doi-asserted-by":"publisher","first-page":"11908","DOI":"10.1021\/acs.jcim.5c02398","article-title":"ColabReaction:\nAccelerating transition\nstate searches with machine learning potentials on Google Colaboratory","volume":"65","author":"Karasawa","year":"2025","journal-title":"J. Chem. Inf. Model."},{"key":"2026092808090169500_cit46","doi-asserted-by":"publisher","first-page":"21151","DOI":"10.1021\/jacs.6c04423","article-title":"Strategic\nApplications of Single-Atom Skeletal Editing in Natural Product Synthesis","volume":"148","author":"Al-Ahmad","year":"2026","journal-title":"J. Am. Chem. Soc."}],"container-title":["JACS Au"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacsau.6c00833","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jaaucr\/article-pdf\/6\/9\/5207\/66335666\/jacsau.6c00833.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jaaucr\/article-pdf\/6\/9\/5207\/66335666\/jacsau.6c00833.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T12:21:46Z","timestamp":1790598106000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jaaucr\/article\/6\/9\/5207\/5237082\/Formal-Chemoenzymatic-Skeletal-Editing-of"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,30]]},"references-count":46,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2026,7,30]]},"published-print":{"date-parts":[[2026,9,28]]}},"URL":"https:\/\/doi.org\/10.1021\/jacsau.6c00833","relation":{},"ISSN":["2691-3704"],"issn-type":[{"value":"2691-3704","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,30]]}}}