{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,4]],"date-time":"2025-11-04T11:53:14Z","timestamp":1762257194830,"version":"build-2065373602"},"reference-count":75,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2025,9,17]],"date-time":"2025-09-17T00:00:00Z","timestamp":1758067200000},"content-version":"vor","delay-in-days":16,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["enviromicro-journals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Microbial Biotechnology"],"published-print":{"date-parts":[[2025,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Bacterial Rieske non\u2010heme iron oxygenases catalyse the transformation of a wide range of aromatic compounds to vicinal\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010dihydrodiols. Such compounds have been successfully applied in chemoenzymatic synthetic routes for, for example, pharmaceuticals, natural products and polymers. In the case of benzoate, only (1\n                    <jats:italic>S<\/jats:italic>\n                    ,2\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010\n                    <jats:italic>cis<\/jats:italic>\n                    \u20101,2\u2010dihydroxy\u20102\u2010hydrobenzoate is readily accessible via enzymatic transformation, but not the regioisomeric\n                    <jats:italic>cis<\/jats:italic>\n                    \u20102,3\u2010dihydroxy\u20102,3\u2010dihydrobenzoate (2,3\u2010DD) or\n                    <jats:italic>cis<\/jats:italic>\n                    \u20103,4\u2010dihydroxy\u20103,4\u2010dihydrobenzoate. While trace amounts of putative\n                    <jats:italic>cis<\/jats:italic>\n                    \u20102,3\u2010DD have been obtained before by using\n                    <jats:italic>p<\/jats:italic>\n                    \u2010cumate 2,3\u2010dioxygenase (PCDO) or a combination of chlorobenzene dioxygenase and nitrilase, none of these approaches enabled its production and isolation at a greater scale for potential use as a chiral building block in organic synthesis. We here provide a protocol for biotransformation of benzoate yielding (2\n                    <jats:italic>R<\/jats:italic>\n                    ,3\n                    <jats:italic>S<\/jats:italic>\n                    )\u20102,3\u2010dihydroxy\u20102,3\u2010dihydrobenzoate using the PCDO of\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>Pseudomonas citronellolis<\/jats:italic>\n                    <\/jats:styled-content>\n                    strain EB200 with negligible formation of side products. An isolation procedure suitable for production of the 2,3\u2010DD sodium salt monohydrate at high purity (&gt;\u200995%) at a gram scale, and a comprehensive characterisation of this novel metabolite is given.\n                  <\/jats:p>","DOI":"10.1111\/1751-7915.70228","type":"journal-article","created":{"date-parts":[[2025,9,17]],"date-time":"2025-09-17T16:25:13Z","timestamp":1758126313000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Biotechnological Production, Isolation and Characterisation of (\n                    <scp>\n                      2\n                      <i>R<\/i>\n                    <\/scp>\n                    ,\n                    <scp>\n                      3\n                      <i>S<\/i>\n                    <\/scp>\n                    )\u20102,3\u2010Dihydroxy\u20102,3\u2010Dihydrobenzoate"],"prefix":"10.1111","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4261-0718","authenticated-orcid":false,"given":"Martina","family":"Kiel","sequence":"first","affiliation":[{"name":"Institute of Sanitary Engineering, Water Quality and Solid Waste Management University of Stuttgart  Stuttgart Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5252-4485","authenticated-orcid":false,"given":"Israel","family":"Barrantes","sequence":"additional","affiliation":[{"name":"Microbial Interactions and Processes Research Group Helmholtz Centre for Infection Research  Braunschweig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3106-3421","authenticated-orcid":false,"given":"Dietmar H.","family":"Pieper","sequence":"additional","affiliation":[{"name":"Microbial Interactions and Processes Research Group Helmholtz Centre for Infection Research  Braunschweig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7273-2962","authenticated-orcid":false,"given":"Karl\u2010Heinrich","family":"Engesser","sequence":"additional","affiliation":[{"name":"Institute of Sanitary Engineering, Water Quality and Solid Waste Management University of Stuttgart  Stuttgart Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,9,17]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2836(05)80360-2"},{"key":"e_1_2_9_3_1","doi-asserted-by":"crossref","unstructured":"Anastas P. T. andJ. C.Warner.2000.\u201cGreen Chemistry: Oxford University PressOxford.\u201d","DOI":"10.1093\/oso\/9780198506980.001.0001"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1042\/bj1940607"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/0922-338X(96)82207-0"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1462-2920.2010.02233.x"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1128\/JB.186.15.5062-5077.2004"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M501988200"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39830000954"},{"key":"e_1_2_9_10_1","first-page":"53","volume-title":"Strategies and Tactics in Organic Synthesis","author":"Bedard K.","year":"2021"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/P19950002861"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1006\/mben.1998.0107"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-2911(08)60066-1"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(76)91020-2"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.129.3.1356-1364.1977"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1128\/MMBR.65.4.523-569.2001"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1093\/database\/bau118"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.178.5.1351-1362.1996"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.179.10.3171-3180.1997"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1128\/JB.183-1.109-118.2001"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6968.1990.tb04251.x"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/b902577b"},{"key":"e_1_2_9_23_1","first-page":"50","article-title":"Bio\u2010Inspired Arene Cis\u2010Dihydroxylation by a Non\u2010Haem Iron Catalyst Modeling the Action of Naphthalene Dioxygenase","volume":"1","author":"Feng Y.","year":"2009","journal-title":"Chemical Communications"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200204265"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi00847a031"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3QO00057E"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.173.23.7540-7548.1991"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1007\/s002530050649"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2015.115"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(76)90544-1"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.01494-06"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1087946"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/P19950002647"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-9861(68)90020-9"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01025a058"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.1462-2920.2002.00370.x"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/0471264180.or063.02"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/a703071a"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39720000784"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.gene.2012.05.004"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.8b02877"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6941.2008.00436.x"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1128\/JB.00430-12"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/20.13.3479"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1128\/JB.182.13.3784-3793.2000"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkab902"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-019-10210-3"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.69.3.1564-1572.2003"},{"key":"e_1_2_9_49_1","doi-asserted-by":"publisher","DOI":"10.1099\/13500872-141-2-485"},{"key":"e_1_2_9_50_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M502585200"},{"key":"e_1_2_9_51_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1976.tb10019.x"},{"key":"e_1_2_9_52_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.95.11.6419"},{"key":"e_1_2_9_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)99839-X"},{"key":"e_1_2_9_54_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-540-77587-4_60"},{"key":"e_1_2_9_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar500427k"},{"key":"e_1_2_9_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202100829"},{"key":"e_1_2_9_57_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.108.1.89-94.1971"},{"key":"e_1_2_9_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi00789a017"},{"issue":"2","key":"e_1_2_9_59_1","first-page":"30P","article-title":"Bacterial Oxidation of 2,3\u2010Dihydroxybenzoic Acid\u2014A New Oxygenase","volume":"99","author":"Ribbons D. W.","year":"1966","journal-title":"Biochemical Journal"},{"key":"e_1_2_9_60_1","doi-asserted-by":"publisher","DOI":"10.1042\/bj1170028P"},{"key":"e_1_2_9_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/0378-1119(94)90324-7"},{"key":"e_1_2_9_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biortech.2010.04.052"},{"key":"e_1_2_9_63_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.174.3.711-724.1992"},{"key":"e_1_2_9_64_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2594"},{"key":"e_1_2_9_65_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pep.2005.01.016"},{"volume-title":"NCIB 9816\u20134 in Escherichia coli","year":"1991","author":"Suen W.\u2010C.","key":"e_1_2_9_66_1"},{"key":"e_1_2_9_67_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-008-1603-2"},{"key":"e_1_2_9_68_1","doi-asserted-by":"publisher","DOI":"10.1263\/jbb.100.517"},{"key":"e_1_2_9_69_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)91382-6"},{"key":"e_1_2_9_70_1","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gks596"},{"key":"e_1_2_9_71_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.271.8.4009"},{"key":"e_1_2_9_72_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jbiotec.2020.09.012"},{"key":"e_1_2_9_73_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.124.1.7-13.1975"},{"key":"e_1_2_9_74_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcatb.2005.11.006"},{"key":"e_1_2_9_75_1","doi-asserted-by":"publisher","DOI":"10.1016\/0304-4165(69)90300-6"},{"key":"e_1_2_9_76_1","doi-asserted-by":"publisher","DOI":"10.1128\/jb.106.1.51-57.1971"}],"container-title":["Microbial Biotechnology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/sfamjournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/1751-7915.70228","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,4]],"date-time":"2025-11-04T11:47:33Z","timestamp":1762256853000},"score":1,"resource":{"primary":{"URL":"https:\/\/sfamjournals.onlinelibrary.wiley.com\/doi\/10.1111\/1751-7915.70228"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,9]]},"references-count":75,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2025,9]]}},"alternative-id":["10.1111\/1751-7915.70228"],"URL":"https:\/\/doi.org\/10.1111\/1751-7915.70228","archive":["Portico"],"relation":{},"ISSN":["1751-7915","1751-7915"],"issn-type":[{"type":"print","value":"1751-7915"},{"type":"electronic","value":"1751-7915"}],"subject":[],"published":{"date-parts":[[2025,9]]},"assertion":[{"value":"2025-05-28","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-08-25","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-09-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70228"}}