{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,18]],"date-time":"2026-04-18T07:25:44Z","timestamp":1776497144725,"version":"3.51.2"},"reference-count":49,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2024,3,6]],"date-time":"2024-03-06T00:00:00Z","timestamp":1709683200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2024,4,16]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Cupin dioxygenases such as salicylate 1,2\u2010dioxygense (SDO) perform aromatic C\u2212C bond scission via a 3\u2010His motif tethered iron cofactor. Here, transient kinetics measurements are used to monitor the catalytic cycle of SDO by using a nitro\u2010substituted substrate analog, 3\u2010nitrogentisate. Compared to the natural substrate, the nitro group reduces the enzymatic <jats:italic>k<\/jats:italic><jats:sub>cat<\/jats:sub> by 500\u2010fold, thereby facilitating the detection and kinetic characterization of reaction intermediates. Sums and products of reciprocal relaxation times derived from kinetic measurements were found to be linearly dependent on O<jats:sub>2<\/jats:sub> concentration, suggesting reversible formation of two distinct intermediates. Dioxygen binding to the metal cofactor takes place with a forward rate of 5.9\u00d710<jats:sup>3<\/jats:sup>\u2005M<jats:sup>\u22121<\/jats:sup>\u2009s<jats:sup>\u22121<\/jats:sup>: two orders of magnitude slower than other comparable ring\u2010cleaving dioxygenses. Optical chromophore of the first intermediate is distinct from the <jats:italic>in\u2005situ<\/jats:italic> generated SDO Fe(III)\u2212O<jats:sub>2<\/jats:sub>\u22c5<jats:sup>\u2212<\/jats:sup> complex but closer to the enzyme\u2010substrate precursor.<\/jats:p>","DOI":"10.1002\/cbic.202400023","type":"journal-article","created":{"date-parts":[[2024,2,16]],"date-time":"2024-02-16T11:09:50Z","timestamp":1708081790000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Oxygen Activation in Aromatic Ring Cleaving Salicylate Dioxygenase: Detection of Reaction Intermediates with a Nitro\u2010substituted Substrate Analog"],"prefix":"10.1002","volume":"25","author":[{"given":"Qian","family":"Wang","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Staten Island The City University of New York  2800 Victory Blvd. Staten Island New York 10314 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hanbin","family":"Li","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Staten Island The City University of New York  2800 Victory Blvd. Staten Island New York 10314 United States"},{"name":"Ph.D. Programs in Chemistry and Physics The Graduate Center of the City University of New York  New York 10016 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Uran","family":"Bujupi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Staten Island The City University of New York  2800 Victory Blvd. Staten Island New York 10314 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Janosch","family":"Gr\u00f6ning","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Mikrobiologie Universit\u00e4t Stuttgart  Allmandring 31 70569 Stuttgart Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andreas","family":"Stolz","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Mikrobiologie Universit\u00e4t Stuttgart  Allmandring 31 70569 Stuttgart Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5661-9265","authenticated-orcid":false,"given":"Angelo","family":"Bongiorno","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Staten Island The City University of New York  2800 Victory Blvd. Staten Island New York 10314 United States"},{"name":"Ph.D. Programs in Chemistry and Physics The Graduate Center of the City University of New York  New York 10016 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8637-6129","authenticated-orcid":false,"given":"Rupal","family":"Gupta","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Staten Island The City University of New York  2800 Victory Blvd. Staten Island New York 10314 United States"},{"name":"Ph.D. Programs in Biochemistry The Graduate Center of the City University of New York  New York 10016 United States"},{"name":"Ph.D. Programs in Chemistry and Physics The Graduate Center of the City University of New York  New York 10016 United States"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,3,6]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1080\/10409230600817422"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/0076-6879(90)88019-7"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)45688-8"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)39326-3"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2003.08.016"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1128\/JB.183.23.6936-6942.2001"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1111\/febs.12173"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M313500200"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2008.05.041"},{"key":"e_1_2_9_10_1","volume":"363","author":"Eppinger E.","year":"2015","journal-title":"FEMS Microbiol. Lett."},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijbiomac.2023.124230"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsb.2012.08.007"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsb.2011.11.026"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00775-019-01646-5"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbapap.2015.06.005"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506363"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00775-017-1436-5"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1010015107"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2sc00754a"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b04065"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi2011724"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201701286"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00775-005-0624-x"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00775-016-1431-2"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c04770"},{"key":"e_1_2_9_26_1","volume-title":"Metal ions in Biological Systems","author":"Lipscomb J. D.","year":"1992"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi0484421"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1108965"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi050180v"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi048690x"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1134697"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1419118112"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)62884-4"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)91929-0"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0609514104"},{"key":"e_1_2_9_36_1","doi-asserted-by":"crossref","DOI":"10.1107\/S2059798323004199","volume":"79","author":"Eppinger E.","year":"2023","journal-title":"Acta Crystallogr. Sect. D"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic001185d"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja504410s"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms6440"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201502367"},{"key":"e_1_2_9_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.6b01732"},{"key":"e_1_2_9_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi201436n"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi700662d"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac60155a056"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1606"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.37.785"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1039\/b508541a"},{"key":"e_1_2_9_49_1","doi-asserted-by":"publisher","DOI":"10.1039\/b515623h"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.202400023","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:09:43Z","timestamp":1760274583000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.202400023"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,3,6]]},"references-count":49,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2024,4,16]]}},"alternative-id":["10.1002\/cbic.202400023"],"URL":"https:\/\/doi.org\/10.1002\/cbic.202400023","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"value":"1439-4227","type":"print"},{"value":"1439-7633","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,3,6]]},"assertion":[{"value":"2024-01-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-03-06","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202400023"}}