{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,10]],"date-time":"2026-06-10T14:52:56Z","timestamp":1781103176865,"version":"3.54.1"},"reference-count":23,"publisher":"National Academy of Sciences","issue":"14","content-domain":{"domain":["www.pnas.org"],"crossmark-restriction":true},"short-container-title":["Proc. Natl. Acad. Sci. U.S.A."],"published-print":{"date-parts":[[1999,7,6]]},"abstract":"<jats:p>\n                    The flavoprotein 2-aminobenzoyl-CoA monooxygenase\/reductase from the eubacterium\n                    <jats:italic>Azoarcus evansii<\/jats:italic>\n                    catalyzes the dearomatization of 2-aminobenzoyl-CoA. The reaction consists in an O\n                    <jats:sub>2<\/jats:sub>\n                    -dependent monooxygenation at the benzene position 5, which is followed immediately by an NADH-dependent hydrogenation of the intermediate at the same catalytic locus. The reaction was studied by\n                    <jats:sup>1<\/jats:sup>\n                    H,\n                    <jats:sup>2<\/jats:sup>\n                    H, and\n                    <jats:sup>13<\/jats:sup>\n                    C NMR spectroscopy of the products. The main product was characterized as 5-oxo-2-aminocyclohex-1-ene-1-carboxyl-CoA by two-dimensional NMR spectroscopy. Thus, [5-\n                    <jats:sup>2<\/jats:sup>\n                    H]2-aminobenzoyl-CoA was converted into [6-\n                    <jats:sup>2<\/jats:sup>\n                    H]5-oxo-2-aminocyclohex-1-ene-1-carboxyl-CoA, indicating a 5 \u2192 6 shift of the [5-\n                    <jats:sup>2<\/jats:sup>\n                    H] label. Label from NAD\n                    <jats:sup>2<\/jats:sup>\n                    H was transferred to the 3 position of the cyclic eneamine, whereas label from solvent D\n                    <jats:sub>2<\/jats:sub>\n                    O was incorporated into the 4 and the 6 positions of 5-oxo-2-aminocyclohex-1-ene-1-carboxyl-CoA. The labeling pattern is compatible with the monooxygenation proceeding via what is formally an NIH shift, yielding 5-oxo-2-aminocyclohex-1,3-diene-1-carboxyl-CoA as a protein-bound intermediate. It is suggested that this shift in flavin-dependent monooxygenation may have general validity.\n                  <\/jats:p>","DOI":"10.1073\/pnas.96.14.7831","type":"journal-article","created":{"date-parts":[[2002,7,26]],"date-time":"2002-07-26T10:38:21Z","timestamp":1027679901000},"page":"7831-7836","update-policy":"https:\/\/doi.org\/10.1073\/pnas.cm10313","source":"Crossref","is-referenced-by-count":25,"title":["NIH shift in flavin-dependent monooxygenation: Mechanistic studies with 2-aminobenzoyl-CoA monooxygenase\/reductase"],"prefix":"10.1073","volume":"96","author":[{"given":"Steffen","family":"Hartmann","sequence":"first","affiliation":[{"name":"Fakult\u00e4t Biologie, Universit\u00e4t Konstanz, P.O. Box 5560-M644, D-78457 Konstanz, Germany; Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstrasse 4, D-85747 Garching, Germany; and Mikrobiologie, Institut f\u00fcr Biologie II, Universit\u00e4t Freiburg, Sch\u00e4nzlestrasse 1, D-79104 Freiburg, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claus","family":"Hultschig","sequence":"additional","affiliation":[{"name":"Fakult\u00e4t Biologie, Universit\u00e4t Konstanz, P.O. Box 5560-M644, D-78457 Konstanz, Germany; Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstrasse 4, D-85747 Garching, Germany; and Mikrobiologie, Institut f\u00fcr Biologie II, Universit\u00e4t Freiburg, Sch\u00e4nzlestrasse 1, D-79104 Freiburg, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wolfgang","family":"Eisenreich","sequence":"additional","affiliation":[{"name":"Fakult\u00e4t Biologie, Universit\u00e4t Konstanz, P.O. Box 5560-M644, D-78457 Konstanz, Germany; Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstrasse 4, D-85747 Garching, Germany; and Mikrobiologie, Institut f\u00fcr Biologie II, Universit\u00e4t Freiburg, Sch\u00e4nzlestrasse 1, D-79104 Freiburg, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Georg","family":"Fuchs","sequence":"additional","affiliation":[{"name":"Fakult\u00e4t Biologie, Universit\u00e4t Konstanz, P.O. Box 5560-M644, D-78457 Konstanz, Germany; Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstrasse 4, D-85747 Garching, Germany; and Mikrobiologie, Institut f\u00fcr Biologie II, Universit\u00e4t Freiburg, Sch\u00e4nzlestrasse 1, D-79104 Freiburg, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adelbert","family":"Bacher","sequence":"additional","affiliation":[{"name":"Fakult\u00e4t Biologie, Universit\u00e4t Konstanz, P.O. Box 5560-M644, D-78457 Konstanz, Germany; Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstrasse 4, D-85747 Garching, Germany; and Mikrobiologie, Institut f\u00fcr Biologie II, Universit\u00e4t Freiburg, Sch\u00e4nzlestrasse 1, D-79104 Freiburg, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sandro","family":"Ghisla","sequence":"additional","affiliation":[{"name":"Fakult\u00e4t Biologie, Universit\u00e4t Konstanz, P.O. Box 5560-M644, D-78457 Konstanz, Germany; Lehrstuhl f\u00fcr Organische Chemie und Biochemie, Technische Universit\u00e4t M\u00fcnchen, Lichtenbergstrasse 4, D-85747 Garching, Germany; and Mikrobiologie, Institut f\u00fcr Biologie II, Universit\u00e4t Freiburg, Sch\u00e4nzlestrasse 1, D-79104 Freiburg, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"341","published-online":{"date-parts":[[1999,7,6]]},"reference":[{"key":"e_1_3_3_1_2","volume-title":"Chemistry and Biochemistry of Flavoenzymes","author":"van Berkel W J H","year":"1991","unstructured":"W J H van Berkel, F M\u00fcller Chemistry and Biochemistry of Flavoenzymes, ed F M\u00fcller (CRC, Boca Raton, FL) II (1991)."},{"key":"e_1_3_3_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.198400008"},{"key":"e_1_3_3_3_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1749-6632.1986.tb48036.x"},{"key":"e_1_3_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00053a004"},{"key":"e_1_3_3_5_2","first-page":"323","volume-title":"Flavins and Flavoproteins","author":"Ortiz-Maldonado M","year":"1997","unstructured":"M Ortiz-Maldonado, D P Ballou, V Massey Flavins and Flavoproteins, eds K J Stevenson, V Massey, C H Williams (Univ. of Calgary Press, Calgary), pp. 323\u2013326 (1997)."},{"key":"e_1_3_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00346a057"},{"key":"e_1_3_3_7_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1993.tb18383.x"},{"key":"e_1_3_3_8_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1995.tb20386.x"},{"key":"e_1_3_3_9_2","doi-asserted-by":"publisher","DOI":"10.1042\/bj3110353"},{"key":"e_1_3_3_10_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.157.3796.1524"},{"key":"e_1_3_3_11_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1978.tb20905.x"},{"key":"e_1_3_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00037a011"},{"key":"e_1_3_3_13_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1989.tb15159.x"},{"key":"e_1_3_3_14_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1995.tb20609.x"},{"key":"e_1_3_3_15_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1995.0686h.x"},{"key":"e_1_3_3_16_2","doi-asserted-by":"publisher","DOI":"10.1099\/00207713-45-2-327"},{"key":"e_1_3_3_17_2","doi-asserted-by":"publisher","DOI":"10.1128\/aem.48.1.102-107.1984"},{"key":"e_1_3_3_18_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1989.tb15160.x"},{"key":"e_1_3_3_19_2","doi-asserted-by":"publisher","DOI":"10.1128\/jb.173.17.5494-5501.1991"},{"key":"e_1_3_3_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.1270070908"},{"key":"e_1_3_3_21_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1990.tb19131.x"},{"key":"e_1_3_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00681a029"},{"key":"e_1_3_3_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)45925-5"}],"container-title":["Proceedings of the National Academy of Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pnas.org\/doi\/pdf\/10.1073\/pnas.96.14.7831","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,4,13]],"date-time":"2022-04-13T15:44:53Z","timestamp":1649864693000},"score":1,"resource":{"primary":{"URL":"https:\/\/pnas.org\/doi\/full\/10.1073\/pnas.96.14.7831"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1999,7,6]]},"references-count":23,"journal-issue":{"issue":"14","published-print":{"date-parts":[[1999,7,6]]}},"alternative-id":["10.1073\/pnas.96.14.7831"],"URL":"https:\/\/doi.org\/10.1073\/pnas.96.14.7831","relation":{},"ISSN":["0027-8424","1091-6490"],"issn-type":[{"value":"0027-8424","type":"print"},{"value":"1091-6490","type":"electronic"}],"subject":[],"published":{"date-parts":[[1999,7,6]]},"assertion":[{"value":"1998-12-20","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"1999-04-30","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"1999-07-06","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}