{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T19:39:05Z","timestamp":1785267545086,"version":"3.55.0"},"reference-count":29,"publisher":"Wiley","issue":"26","license":[{"start":{"date-parts":[[2020,4,9]],"date-time":"2020-04-09T00:00:00Z","timestamp":1586390400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001342","name":"Department of Science and Technology, Republic of South Africa","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001342","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001321","name":"National Research Foundation","doi-asserted-by":"publisher","award":["c*change PAR02, cSTAR BIO"],"award-info":[{"award-number":["c*change PAR02, cSTAR BIO"]}],"id":[{"id":"10.13039\/501100001321","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":[[2020,6,22]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The self\u2010sufficient cytochrome\u2005P450 monooxygenase CYP505E3 from <jats:italic>Aspergillus terreus<\/jats:italic> catalyzes the regioselective in\u2010chain hydroxylation of alkanes, fatty alcohols, and fatty acids at the \u03c9\u20107 position. It is the first reported P450 to give regioselective in\u2010chain \u03c9\u20107 hydroxylation of C10\u2013C16 <jats:italic>n<\/jats:italic>\u2010alkanes, thereby enabling the one step biocatalytic synthesis of rare alcohols such as 5\u2010dodecanol and 7\u2010tetradecanol. It shows more than 70\u2009% regioselectivity for the eighth carbon from one methyl terminus, and displays remarkably high activity towards decane (TTN\u22488000) and dodecane (TTN\u22482000). CYP505E3 can be used to synthesize the high\u2010value flavour compound \u03b4\u2010dodecalactone via two routes: 1)\u2005conversion of dodecanoic acid into 5\u2010hydroxydodecanoic acid (24\u2009% regioselectivity), which at low pH lactonises to \u03b4\u2010dodecalactone, and 2)\u2005conversion of 1\u2010dodecanol into 1,5\u2010dodecanediol (55\u2009% regioselectivity), which can be converted into \u03b4\u2010dodecalactone by horse liver alcohol dehydrogenase.<\/jats:p>","DOI":"10.1002\/anie.202001055","type":"journal-article","created":{"date-parts":[[2020,3,9]],"date-time":"2020-03-09T03:10:52Z","timestamp":1583723452000},"page":"10359-10362","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":27,"title":["CYP505E3: A Novel Self\u2010Sufficient \u03c9\u20107 In\u2010Chain Hydroxylase"],"prefix":"10.1002","volume":"59","author":[{"given":"Mpeyake Jacob","family":"Maseme","sequence":"first","affiliation":[{"name":"Department of Microbial, Biochemical and Food Biotechnology University of the Free State  P.O. Box 339 Bloemfontein 9300 South Africa"},{"name":"South African DST-NRF Centre of Excellence in Catalysis, c*change University of Cape Town  South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aliz\u00e9","family":"Pennec","sequence":"additional","affiliation":[{"name":"Department of Microbial, Biochemical and Food Biotechnology University of the Free State  P.O. Box 339 Bloemfontein 9300 South Africa"},{"name":"South African DST-NRF Centre of Excellence in Catalysis, c*change University of Cape Town  South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5350-4013","authenticated-orcid":false,"given":"Jacqueline","family":"van Marwijk","sequence":"additional","affiliation":[{"name":"Department of Microbial, Biochemical and Food Biotechnology University of the Free State  P.O. Box 339 Bloemfontein 9300 South Africa"},{"name":"South African DST-NRF Centre of Excellence in Catalysis, c*change University of Cape Town  South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2737-8797","authenticated-orcid":false,"given":"Diederik Johannes","family":"Opperman","sequence":"additional","affiliation":[{"name":"Department of Microbial, Biochemical and Food Biotechnology University of the Free State  P.O. Box 339 Bloemfontein 9300 South Africa"},{"name":"South African DST-NRF Centre of Excellence in Catalysis, c*change University of Cape Town  South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1295-6507","authenticated-orcid":false,"given":"Martha Sophia","family":"Smit","sequence":"additional","affiliation":[{"name":"Department of Microbial, Biochemical and Food Biotechnology University of the Free State  P.O. Box 339 Bloemfontein 9300 South Africa"},{"name":"South African DST-NRF Centre of Excellence in Catalysis, c*change University of Cape Town  South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2020,4,9]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1ob05565h"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.50656"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10562-017-2273-4"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201901242"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201901242"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12896-016-0291-8"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.01806-17"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201801180"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.01091-18"},{"key":"e_1_2_2_9_1","unstructured":"\u201cHeterlogous Expression of Cytochrome P450 Monooxygenases from Aspergillus Terreus and Cryptococcus Neoformans\u201d: O.\u2005O. Kuloyo University of the Free State 2014."},{"key":"e_1_2_2_10_1","unstructured":"\u201cProcess for Omega-7 Hydroxylation of C12\u2013C16 Fatty Acids Alcohols and Alkanes\u201d:M. S.Smit D. J.Opperman A.Pennec J.vanMarwijk M. J.Maseme A. P.Jiminez EP3365455 2019."},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.4028\/www.scientific.net\/AMR.781-784.1570"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.4315\/0362-028X.JFP-10-512"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2011.10.019"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.5650\/jos.ess19234"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201400410"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00444a040"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/cs400535c"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0146160"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcatb.2010.01.025"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201800533"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201914877"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201914877"},{"key":"e_1_2_2_22_1","first-page":"0","volume":"21","author":"Marella E. R.","year":"2019","journal-title":"Metab. Eng."},{"key":"e_1_2_2_23_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-019-50261-6"},{"key":"e_1_2_2_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201311091"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201311091"},{"key":"e_1_2_2_25_1","first-page":"161","author":"Rusli M. S.","year":"2012","journal-title":"IFEAT Int. Conf."},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00172180"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.202001055","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202001055","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202001055","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202001055","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,5]],"date-time":"2023-09-05T06:12:56Z","timestamp":1693894376000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202001055"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,4,9]]},"references-count":29,"journal-issue":{"issue":"26","published-print":{"date-parts":[[2020,6,22]]}},"alternative-id":["10.1002\/anie.202001055"],"URL":"https:\/\/doi.org\/10.1002\/anie.202001055","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,4,9]]},"assertion":[{"value":"2020-01-20","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-04-09","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}