{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:27:11Z","timestamp":1760315231630,"version":"build-2065373602"},"reference-count":85,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2022,6,14]],"date-time":"2022-06-14T00:00:00Z","timestamp":1655164800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100011889","name":"Diamond Light Source","doi-asserted-by":"publisher","award":["mx-9948"],"award-info":[{"award-number":["mx-9948"]}],"id":[{"id":"10.13039\/100011889","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2022,8,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The asymmetric reduction of ketones to chiral hydroxyl compounds by alcohol dehydrogenases (ADHs) is an established strategy for the provision of valuable precursors for fine chemicals and pharmaceutics. However, most ADHs favor linear aliphatic and aromatic carbonyl compounds, and suitable biocatalysts with preference for cyclic ketones and diketones are still scarce. Among the few candidates, the alcohol dehydrogenase from <jats:italic>Thauera aromatica<\/jats:italic> (ThaADH) stands out with a high activity for the reduction of the cyclic \u03b1\u2010diketone 1,2\u2010cyclohexanedione to the corresponding \u03b1\u2010hydroxy ketone. This study elucidates catalytic and structural features of the enzyme. ThaADH showed a remarkable thermal and pH stability as well as stability in the presence of polar solvents. A thorough description of the substrate scope combined with the resolution and description of the crystal structure, demonstrated a strong preference of ThaADH for cyclic \u03b1\u2010substituted cyclohexanones, and indicated structural determinants responsible for the unique substrate acceptance.<\/jats:p>","DOI":"10.1002\/cbic.202200149","type":"journal-article","created":{"date-parts":[[2022,5,12]],"date-time":"2022-05-12T10:28:32Z","timestamp":1652351312000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Advanced Insights into Catalytic and Structural Features of the Zinc\u2010Dependent Alcohol Dehydrogenase from <i>Thauera aromatica<\/i>"],"prefix":"10.1002","volume":"23","author":[{"given":"Frances","family":"Stark","sequence":"first","affiliation":[{"name":"Professur f\u00fcr Molekulare Biotechnologie Technische Universit\u00e4t Dresden  01062 Dresden Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christoph","family":"Loderer","sequence":"additional","affiliation":[{"name":"Professur f\u00fcr Molekulare Biotechnologie Technische Universit\u00e4t Dresden  01062 Dresden Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mark","family":"Petchey","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York Heslington  York YO10 5DD UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gideon","family":"Grogan","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York Heslington  York YO10 5DD UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2912-546X","authenticated-orcid":false,"given":"Marion B.","family":"Ansorge\u2010Schumacher","sequence":"additional","affiliation":[{"name":"Professur f\u00fcr Molekulare Biotechnologie Technische Universit\u00e4t Dresden  01062 Dresden Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2022,6,14]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/ed1003806"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00203"},{"key":"e_1_2_8_3_1","unstructured":"\u00a0"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-007-1002-0"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-007-1005-x"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(03)00526-3"},{"key":"e_1_2_8_7_1","unstructured":"\u00a0"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00018-008-8589-x"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00018-008-8587-z"},{"key":"e_1_2_8_10_1","unstructured":"\u00a0"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1987.tb13361.x"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.01392-08"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/bit.20004"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac196409010119"},{"key":"e_1_2_8_15_1","unstructured":"\u00a0"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-008-1606-z"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA02066D"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/0141-0229(93)90171-W"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.3109\/10242429309030954"},{"key":"e_1_2_8_20_1","unstructured":"\u00a0"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol070679c"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/0920-5861(94)80126-6"},{"key":"e_1_2_8_23_1","unstructured":"\u00a0"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00888a015"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00381a025"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b02355"},{"key":"e_1_2_8_27_1","unstructured":"\u00a0"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201500100"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CY00169J"},{"key":"e_1_2_8_30_1","unstructured":"\u00a0"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar980062i"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo960932e"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.49.932"},{"key":"e_1_2_8_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(02)01058-2"},{"key":"e_1_2_8_35_1","unstructured":"T. Daussmann H.-G. Hennemann 2004 DE102004029112B4."},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00409663"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200600285"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2015.09.001"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1990.tb15384.x"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201500171"},{"key":"e_1_2_8_41_1","unstructured":"\u00a0"},{"key":"e_1_2_8_42_2","unstructured":"M. Bhattacharjee 2006 Dissertation RWTH Aachen Universit\u00e4t;"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/bit.24857"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b00621"},{"key":"e_1_2_8_45_1","unstructured":"\u00a0"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1263\/jbb.100.318"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.71.7.3633-3641.2005"},{"key":"e_1_2_8_48_1","unstructured":"\u00a0"},{"key":"e_1_2_8_49_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00792-007-0133-7"},{"key":"e_1_2_8_50_2","doi-asserted-by":"publisher","DOI":"10.2331\/fishsci.62.272"},{"key":"e_1_2_8_51_1","unstructured":"\u00a0"},{"key":"e_1_2_8_52_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF01022403"},{"key":"e_1_2_8_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/bit.260371011"},{"key":"e_1_2_8_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/pro.2271"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1991.tb15983.x"},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.03873-12"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0070592"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.1432-1327.1999.00504.x"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja994456w"},{"key":"e_1_2_8_60_1","unstructured":"\u00a0"},{"key":"e_1_2_8_61_2","unstructured":"T. Shanati 2019 Dissertation TU Dresden;"},{"key":"e_1_2_8_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2015.11.027"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-9861(52)90518-3"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201200023"},{"key":"e_1_2_8_65_1","doi-asserted-by":"publisher","DOI":"10.1110\/ps.035428.108"},{"key":"e_1_2_8_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2007.05.022"},{"key":"e_1_2_8_67_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-0716-0270-6_3"},{"key":"e_1_2_8_68_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2019.04.025"},{"key":"e_1_2_8_69_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2836(76)90072-3"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201300788"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)45387-8"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0807529106"},{"key":"e_1_2_8_73_1","doi-asserted-by":"publisher","DOI":"10.1021\/cs501524k"},{"key":"e_1_2_8_74_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10822-015-9878-8"},{"key":"e_1_2_8_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja970982g"},{"key":"e_1_2_8_76_1","first-page":"176","volume-title":"Methods in Enzymology, Vol. 331","author":"Raia C. A.","year":"2001"},{"key":"e_1_2_8_77_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0969-2126(00)00031-9"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202000536"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444909047337"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1107\/S090744491003982X"},{"key":"e_1_2_8_81_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889809045701"},{"key":"e_1_2_8_82_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889897006766"},{"key":"e_1_2_8_83_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2007.05.097"},{"key":"e_1_2_8_84_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444904019158"},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444996012255"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.202200149","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbic.202200149","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.202200149","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T10:14:32Z","timestamp":1760264072000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.202200149"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,6,14]]},"references-count":85,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2022,8,3]]}},"alternative-id":["10.1002\/cbic.202200149"],"URL":"https:\/\/doi.org\/10.1002\/cbic.202200149","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"type":"print","value":"1439-4227"},{"type":"electronic","value":"1439-7633"}],"subject":[],"published":{"date-parts":[[2022,6,14]]},"assertion":[{"value":"2022-03-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-06-14","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202200149"}}