{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T13:36:45Z","timestamp":1792503405057,"version":"4.5.0"},"reference-count":73,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2025,11,17]],"date-time":"2025-11-17T00:00:00Z","timestamp":1763337600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100006206","name":"Biological and Environmental Research","doi-asserted-by":"publisher","award":["ERKP886"],"award-info":[{"award-number":["ERKP886"]}],"id":[{"id":"10.13039\/100006206","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100006206","name":"Biological and Environmental Research","doi-asserted-by":"publisher","award":["DE\u2010SC0018409"],"award-info":[{"award-number":["DE\u2010SC0018409"]}],"id":[{"id":"10.13039\/100006206","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000015","name":"U.S. Department of Energy","doi-asserted-by":"publisher","award":["DE\u2010AC36\u201008GO28308"],"award-info":[{"award-number":["DE\u2010AC36\u201008GO28308"]}],"id":[{"id":"10.13039\/100000015","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":[[2026,1,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Existing methods for lignin deconstruction to aromatic monomers primarily cleave carbon\u2013oxygen bonds within the polymer, resulting in sub\u2010optimal monomer yields and formation of oligomers that retain intact carbon\u2013carbon bonds. Here, we demonstrate that copper\u2010catalyzed aerobic oxidation under aqueous alkaline conditions promotes oxidative cleavage of carbon\u2013carbon bonds in lignin oligomers derived from reductive catalytic fractionation (RCF) of pine and poplar biomass. Fundamental insights are gained from reactions of model compounds that resemble subunits present in RCF oligomers. Optimal results are achieved in a flow reactor that provides precise control over O\n                    <jats:sub>2<\/jats:sub>\n                    delivery, temperature, and reaction residence time. The Cu\u2010catalyzed aerobic oxidation conditions access aromatic monomers in 19 and 34 wt% monomer yields, respectively, from pine\u2010 and poplar\u2010derived RCF oligomers. Overall, the sequence consisting of biomass RCF into monomers and oligomers followed by oxidative deconstruction of the RCF oligomers generates substantially higher yields of aromatic monomers from lignin. Engineered strains of\n                    <jats:italic>Pseudomonas putida<\/jats:italic>\n                    support biological funneling of the oligomer\u2010derived oxygenated aromatic compounds into\n                    <jats:italic>cis<\/jats:italic>\n                    ,\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010muconic acid from pine or 2\u2010pyrone\u20104,6\u2010dicarboxylic acid from poplar.\n                  <\/jats:p>","DOI":"10.1002\/anie.202515588","type":"journal-article","created":{"date-parts":[[2025,11,17]],"date-time":"2025-11-17T08:18:01Z","timestamp":1763367481000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Cu\u2010Catalyzed Aerobic Oxidative C\u2500C Cleavage in Lignin\u2010Derived Oligomers and Biological Funneling of the Monomeric Products"],"prefix":"10.1002","volume":"65","author":[{"given":"Surajudeen","family":"Omolabake","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Wisconsin\u2010Madison  1101 University Avenue Madison Wisconsin 53706 USA"},{"name":"Wisconsin Energy Institute University of Wisconsin\u2010Madison  Madison Wisconsin 53726 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dillon T.","family":"Hofsommer","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Wisconsin\u2010Madison  1101 University Avenue Madison Wisconsin 53706 USA"},{"name":"Wisconsin Energy Institute University of Wisconsin\u2010Madison  Madison Wisconsin 53726 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kathryn M.","family":"Mains","sequence":"additional","affiliation":[{"name":"Renewable Resources and Enabling Sciences Center National Renewable Energy Laboratory  Golden Colorado 80401 USA"},{"name":"Center for Bioenergy Innovation Oak Ridge National Laboratory  Oak Ridge Tennessee 37830 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chad T.","family":"Palumbo","sequence":"additional","affiliation":[{"name":"Renewable Resources and Enabling Sciences Center National Renewable Energy Laboratory  Golden Colorado 80401 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Davide","family":"Rigo","sequence":"additional","affiliation":[{"name":"Renewable Resources and Enabling Sciences Center National Renewable Energy Laboratory  Golden Colorado 80401 USA"},{"name":"Center for Bioenergy Innovation Oak Ridge National Laboratory  Oak Ridge Tennessee 37830 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Allison Z.","family":"Werner","sequence":"additional","affiliation":[{"name":"Renewable Resources and Enabling Sciences Center National Renewable Energy Laboratory  Golden Colorado 80401 USA"},{"name":"Center for Bioenergy Innovation Oak Ridge National Laboratory  Oak Ridge Tennessee 37830 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gregg T.","family":"Beckham","sequence":"additional","affiliation":[{"name":"Renewable Resources and Enabling Sciences Center National Renewable Energy Laboratory  Golden Colorado 80401 USA"},{"name":"Center for Bioenergy Innovation Oak Ridge National Laboratory  Oak Ridge Tennessee 37830 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9000-7665","authenticated-orcid":false,"given":"Shannon S.","family":"Stahl","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Wisconsin\u2010Madison  1101 University Avenue Madison Wisconsin 53706 USA"},{"name":"Wisconsin Energy Institute University of Wisconsin\u2010Madison  Madison Wisconsin 53726 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,11,17]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900354u"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1246843"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00155"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.copbio.2016.02.030"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC03061G"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00588"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00566K"},{"key":"e_1_2_7_8_1","first-page":"99","volume-title":"Advances in Inorganic Chemistry","author":"Cui Y.","year":"2021"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-030-00590-0_3"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00134A"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC01555F"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.joule.2017.10.004"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC04182C"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1GC03822B"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570-024-00652-9"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5EE00204D"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.copbio.2018.12.005"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0EE02870C"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aau1567"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC02263F"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2IM00059H"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2019.03.007"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1038\/s44286-023-00006-0"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00783-2"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.3c00813"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-45038-z"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/b901838g"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ie950267k"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ed074p1055"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.5b01344"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8GC00502H"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.1c00729"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1GC02102H"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2GC03333J"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.3c01309"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.joule.2024.08.015"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00350570"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00350807"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00350692"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/op9900028"},{"key":"e_1_2_7_41_1","first-page":"141","volume-title":"Biomass as Energy Resource","author":"Backa S.","year":"2012"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biotechadv.2016.10.001"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1111\/1758\u20102229.12597"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biotechadv.2019.02.016"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/9781788010351-00290"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ymben.2021.12.010"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ymben.2021.02.005"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf00019a003"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10086\u2010006\u20100832\u20101"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC01334H"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2016.10.034"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201700101"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202000989"},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC05171G"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.iecr.0c05085"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/ceat.270190206"},{"key":"e_1_2_7_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar500359m"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201409318"},{"key":"e_1_2_7_59_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC00992K"},{"key":"e_1_2_7_60_1","doi-asserted-by":"publisher","DOI":"10.1021\/op400207f"},{"key":"e_1_2_7_61_1","unstructured":"Studies of model compounds and RCF oligomers were conducted in parallel. The conditions used for flow oxidation of model compounds were based on conditions optimized for reactions of RCF oligomers. The optimization data are provided in section 5 of the Supporting Information."},{"key":"e_1_2_7_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.copbio.2019.02.019"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.arplant.54.031902.134938"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xcrp.2025.102687"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/bit.24793"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1186\/s13068\u2010016\u20100442\u20100"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1246748"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253\u2010020\u201010811\u20109"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.copbio.2023.103025"},{"key":"e_1_2_7_70_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.00136\u201024"},{"key":"e_1_2_7_71_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC01165E"},{"key":"e_1_2_7_72_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8GC02519C"},{"key":"e_1_2_7_73_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8GC03504K"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202515588","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,1,10]],"date-time":"2026-01-10T15:13:16Z","timestamp":1768057996000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202515588"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,11,17]]},"references-count":73,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2026,1,9]]}},"alternative-id":["10.1002\/anie.202515588"],"URL":"https:\/\/doi.org\/10.1002\/anie.202515588","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,11,17]]},"assertion":[{"value":"2025-07-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-10-29","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e15588"}}