{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,20]],"date-time":"2026-09-20T04:06:30Z","timestamp":1789877190712,"version":"4.0.1"},"reference-count":81,"publisher":"Wiley","issue":"38","license":[{"start":{"date-parts":[[2026,7,16]],"date-time":"2026-07-16T00:00:00Z","timestamp":1784160000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,7,16]],"date-time":"2026-07-16T00:00:00Z","timestamp":1784160000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["534926425"],"award-info":[{"award-number":["534926425"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["GR 1861\/13\u20131"],"award-info":[{"award-number":["GR 1861\/13\u20131"]}],"id":[{"id":"10.13039\/501100001659","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":[[2026,9,14]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Non\u2010canonical terpene biosynthesis expands structural diversity beyond the classical C\n                    <jats:sub>5n<\/jats:sub>\n                    logic. Here we report the discovery of descartane, a C\n                    <jats:sub>16<\/jats:sub>\n                    homosesquiterpene with an unprecedented scaffold produced by a bacterial type I terpene cyclase from\n                    <jats:italic>Morganella morganii<\/jats:italic>\n                    (MmTC). Unlike most terpene cyclase products, descartane is fully saturated and lacks both alkene and alcohol functions, while containing a cyclopropane ring formed in an unusual termination step. Functional characterisation demonstrated that MmTC converts \u03b1\u2010presodorifen pyrophosphate (\u03b1\u2010PSPP) into descartane. The cyclisation cascade was investigated by extensive isotopic labelling experiments and density functional theory (DFT) calculations, revealing a complex pathway involving fragmentation\u2010recombination, multiple hydride shifts, and cyclopropane formation. Site\u2010directed mutagenesis identified active site residues that control product formation and redirect the cascade towards related terpenes, including voltairene, malebranchene, de\u2010beauvoirol, and pythagorene. These findings establish the biosynthetic origin of descartane and show how subtle changes in the active site can reprogram complex terpene cyclisation cascades.\n                  <\/jats:p>","DOI":"10.1002\/anie.1585472","type":"journal-article","created":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T05:29:08Z","timestamp":1784266148000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Biosynthesis of the Fully Saturated C\n                    <sub>16<\/sub>\n                    Homosesquiterpene Descartane Through Deprotonation With Cyclopropanation"],"prefix":"10.1002","volume":"65","author":[{"given":"Kexin","family":"Yang","sequence":"first","affiliation":[{"name":"Kekul\u00e9 Institute of Organic Chemistry and Biochemistry University of Bonn  Bonn Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philip","family":"Troycke","sequence":"additional","affiliation":[{"name":"Center for Protein Assemblies Department of Chemistry, TU Munich Garching Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1814-8818","authenticated-orcid":false,"given":"Bernd","family":"Goldfuss","sequence":"additional","affiliation":[{"name":"Department of Chemistry Institute of Organic Chemistry University of Cologne  Cologne Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1660-340X","authenticated-orcid":false,"given":"Michael","family":"Groll","sequence":"additional","affiliation":[{"name":"Center for Protein Assemblies Department of Chemistry, TU Munich Garching Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0102-0631","authenticated-orcid":false,"given":"Jeroen S.","family":"Dickschat","sequence":"additional","affiliation":[{"name":"Kekul\u00e9 Institute of Organic Chemistry and Biochemistry University of Bonn  Bonn Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,16]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19580702403"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.18872390102"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02167631"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(00)89625\u20102"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo050449g"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja077792i"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.2007.29"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.202300101"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.22.508"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200702496"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200702496"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0802312105"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja803639g"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202418613"},{"key":"e_1_2_8_14_2","volume":"136","year":"2024","journal-title":"Angewandte Chemie"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00026a012"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202525672"},{"key":"e_1_2_8_16_2","volume":"138","year":"2026","journal-title":"Angewandte Chemie"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905680"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b08510"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41589\u2010023\u201001445\u20109"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2024.09.002"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010023\u201001223\u2010z"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202408809"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202408809"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202303692"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202303692"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202412040"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202412040"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c21930"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5c15311"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2026.102948"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijbiomac.2026.151065"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.277.5333.1815"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403648"},{"key":"e_1_2_8_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201403648"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1006\/abbi.2000.1734"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.231313098"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.19123870102"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(01)90615\u2010X"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(01)99113\u20100"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)97854-8"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(01)87315\u20109"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031\u20109422(92)80385\u2010R"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202313789"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202313789"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507615"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201507615"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.2007.56"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201803800"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201803800"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201608971"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201608971"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1128\/JB.181.15.4499\u20104504.1999"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201809954"},{"key":"e_1_2_8_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201809954"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201605425"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201605425"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021\u20109258(18)99800\u20105"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201612439"},{"key":"e_1_2_8_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201612439"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586\u2010024\u201007487\u2010w"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003\u20102697(76)90527\u20103"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/om100106e"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c00278"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.21759"},{"key":"e_1_2_8_54_1","unstructured":"M. J.Frisch G. W.Trucks H. B.Schlegel et\u00a0al. \u201cGaussian 16 Revision C.01 \u201dGaussian Inc. 2019."},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201200497"},{"key":"e_1_2_8_56_1","unstructured":"G.Luchini J. V.Alegre\u2010Requena Y.Guan I.Funes\u2010Ardoiz andR. S.Paton \u201cGoodVibes v3.0.1 \u201dGoodVibes 2019."},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.4952647"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1039\/b508541a"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.70019"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemphys.2008.10.036"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202205735"},{"key":"e_1_2_8_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202205735"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.1c00746"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CP06869D"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.9b00143"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC00621E"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.24922"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jctc.2c00239"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.1585472","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.1585472","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.1585472","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T09:08:30Z","timestamp":1789376910000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.1585472"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,16]]},"references-count":81,"journal-issue":{"issue":"38","published-print":{"date-parts":[[2026,9,14]]}},"alternative-id":["10.1002\/anie.1585472"],"URL":"https:\/\/doi.org\/10.1002\/anie.1585472","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,16]]},"assertion":[{"value":"2026-04-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-06-17","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-07-16","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e1585472"}}