{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T14:58:38Z","timestamp":1790261918627,"version":"4.1.0"},"reference-count":119,"publisher":"Wiley","issue":"43","license":[{"start":{"date-parts":[[2018,10,8]],"date-time":"2018-10-08T00:00:00Z","timestamp":1538956800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/100010663","name":"H2020 European Research Council","doi-asserted-by":"publisher","award":["638271"],"award-info":[{"award-number":["638271"]}],"id":[{"id":"10.13039\/100010663","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":[[2018,10,22]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We report an unprecedented catalytically promiscuous activity of the copper\u2010dependent enzyme galactose oxidase. The enzyme catalyses the one\u2010pot conversion of alcohols into the related nitriles under mild reaction conditions in ammonium buffer, consuming ammonia as the source of nitrogen and dioxygen (from air at atmospheric pressure) as the only oxidant. Thus, this green method does not require either cyanide salts, toxic metals, or undesired oxidants in stoichiometric amounts. The substrate scope of the reaction includes benzyl and cinnamyl alcohols as well as 4\u2010 and 3\u2010pyridylmethanol, giving access to valuable chemical compounds. The oxidation proceeds through oxidation from alcohol to aldehyde, in\u2005situ imine formation, and final direct oxidation to nitrile.<\/jats:p>","DOI":"10.1002\/anie.201809411","type":"journal-article","created":{"date-parts":[[2018,9,3]],"date-time":"2018-09-03T13:25:13Z","timestamp":1535981113000},"page":"14240-14244","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":49,"title":["Catalytic Promiscuity of Galactose Oxidase: A Mild Synthesis of Nitriles from Alcohols, Air, and Ammonia"],"prefix":"10.1002","volume":"57","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0333-8309","authenticated-orcid":false,"given":"Jan","family":"Vil\u00edm","sequence":"first","affiliation":[{"name":"Van't Hoff Institute for Molecular Sciences, HIMS-Biocat University of Amsterdam  Science Park 904 1098 XH Amsterdam The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9942-9226","authenticated-orcid":false,"given":"Tanja","family":"Knaus","sequence":"additional","affiliation":[{"name":"Van't Hoff Institute for Molecular Sciences, HIMS-Biocat University of Amsterdam  Science Park 904 1098 XH Amsterdam The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6771-5102","authenticated-orcid":false,"given":"Francesco G.","family":"Mutti","sequence":"additional","affiliation":[{"name":"Van't Hoff Institute for Molecular Sciences, HIMS-Biocat University of Amsterdam  Science Park 904 1098 XH Amsterdam The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,10,8]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-biochem-030409-143718"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1038\/nbt1519"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201001664"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature20569"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b05468"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500217"},{"key":"e_1_2_2_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500217"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201510554"},{"key":"e_1_2_2_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201510554"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201501244"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsmacrolett.7b00950"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201700247"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1231434"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201200676"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201600596"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201700261"},{"key":"e_1_2_2_17_1","unstructured":"\u00a0"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acssynbio.7b00072"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/sb500303q"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ymben.2017.04.009"},{"key":"e_1_2_2_21_1","unstructured":"\u00a0"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1378881"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900716q"},{"key":"e_1_2_2_24_1","unstructured":"\u00a0"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00819a035"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)88524-0"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1341227"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC04907A"},{"key":"e_1_2_2_29_1","unstructured":"\u00a0"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.18840170219"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19190520840"},{"key":"e_1_2_2_32_1","unstructured":"\u00a0"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15004a"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206168"},{"key":"e_1_2_2_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206168"},{"key":"e_1_2_2_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6QO00390G"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b10945"},{"key":"e_1_2_2_37_1","unstructured":"\u00a0"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201412256"},{"key":"e_1_2_2_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201412256"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo3008258"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0030-1261181"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1339904"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b02333"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b01632"},{"key":"e_1_2_2_44_1","unstructured":"\u00a0"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1087967"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-967954"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2003-42431"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200250779"},{"key":"e_1_2_2_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200250779"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200501853"},{"key":"e_1_2_2_49_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200501853"},{"key":"e_1_2_2_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo2004956"},{"key":"e_1_2_2_51_1","unstructured":"\u00a0"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol500075h"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b03011"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo025960d"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0260977"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)02644-8"},{"key":"e_1_2_2_57_1","unstructured":"\u00a0"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol101094u"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2008-1078491"},{"key":"e_1_2_2_60_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms15240"},{"key":"e_1_2_2_61_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527684625"},{"key":"e_1_2_2_62_1","unstructured":"\u00a0"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol400459y"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1341124"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1338489"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2002-33906"},{"key":"e_1_2_2_67_1","unstructured":"\u00a0"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300361"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201400718"},{"key":"e_1_2_2_70_1","unstructured":"\u00a0"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1177(98)00080-0"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.65.2666"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201402612"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201702952"},{"key":"e_1_2_2_74_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201702952"},{"key":"e_1_2_2_75_1","unstructured":"\u00a0"},{"key":"e_1_2_2_76_2","first-page":"26","volume-title":"Science of Synthesis Biocatalysis in Organic Synthesis 2","author":"Steiner K.","year":"2015"},{"key":"e_1_2_2_77_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6OB00934D"},{"key":"e_1_2_2_78_2","doi-asserted-by":"publisher","DOI":"10.2174\/18722083113076660010"},{"key":"e_1_2_2_79_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10529-013-1353-9"},{"key":"e_1_2_2_80_1","unstructured":"\u00a0"},{"key":"e_1_2_2_81_2","first-page":"507","volume-title":"Science of Synthesis Biocatalysis in Organic Synthesis 2","author":"Elenkov M. Majeri\u0107","year":"2015"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-016-7750-y"},{"key":"e_1_2_2_83_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6GC02003H"},{"key":"e_1_2_2_84_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201504505"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201504505"},{"key":"e_1_2_2_85_1","doi-asserted-by":"publisher","DOI":"10.2323\/jgam.2016.02.004"},{"key":"e_1_2_2_86_1","unstructured":"\u00a0"},{"key":"e_1_2_2_87_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11103-016-0459-6"},{"key":"e_1_2_2_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/2211-5463.12170"},{"key":"e_1_2_2_89_1","unstructured":"\u00a0"},{"key":"e_1_2_2_90_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200700689"},{"key":"e_1_2_2_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201100380"},{"key":"e_1_2_2_92_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ra20800h"},{"key":"e_1_2_2_93_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201500218"},{"key":"e_1_2_2_94_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC00707K"},{"key":"e_1_2_2_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.5b00278"},{"key":"e_1_2_2_96_1","unstructured":"\u00a0"},{"key":"e_1_2_2_97_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.abb.2004.08.034"},{"key":"e_1_2_2_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi8010835"},{"key":"e_1_2_2_99_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jinorgbio.2017.08.028"},{"key":"e_1_2_2_100_1","first-page":"56","volume-title":"CRC Handbook of Chemistry and Physics","year":"2004"},{"key":"e_1_2_2_101_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201800343"},{"key":"e_1_2_2_101_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201800343"},{"key":"e_1_2_2_102_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b00043"},{"key":"e_1_2_2_103_1","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201600121"},{"key":"e_1_2_2_104_1","first-page":"78","volume-title":"Chemistry and Technology of Flavours and Fragrances","author":"Rowe D. J.","year":"2005"},{"key":"e_1_2_2_105_1","unstructured":"\u00a0"},{"key":"e_1_2_2_106_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm100762r"},{"key":"e_1_2_2_107_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201700875"},{"key":"e_1_2_2_108_1","unstructured":"\u00a0"},{"key":"e_1_2_2_109_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.60.1391"},{"key":"e_1_2_2_110_2","unstructured":"Lonza Full-Year Report 2006 2007."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201809411","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201809411","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,11]],"date-time":"2023-09-11T03:51:06Z","timestamp":1694404266000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201809411"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,10,8]]},"references-count":119,"journal-issue":{"issue":"43","published-print":{"date-parts":[[2018,10,22]]}},"alternative-id":["10.1002\/anie.201809411"],"URL":"https:\/\/doi.org\/10.1002\/anie.201809411","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,10,8]]},"assertion":[{"value":"2018-08-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-10-08","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}