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Oxidácia R 1 NHR 2 pomocou O 2 a cyklohexanón monooxigenázy

Oxidácia R 1 NHR 2 pomocou O 2 a cyklohexanón monooxigenázy. Seminárnu prácu vypracoval: Miroslav Horváth. CHMO . EC 1.14.13.22 oxido-reduktáza (60 kDa) FAD/O 2 → oxidant ; NADPH/NADP + → redox systém účinky obdobné peroxikyselinám

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Oxidácia R 1 NHR 2 pomocou O 2 a cyklohexanón monooxigenázy

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  1. Oxidácia R1NHR2 pomocou O2 a cyklohexanón monooxigenázy Seminárnu prácu vypracoval: Miroslav Horváth

  2. CHMO • EC 1.14.13.22 • oxido-reduktáza (60 kDa) • FAD/O2 → oxidant ; NADPH/NADP+ →redox systém • účinky obdobné peroxikyselinám • primárne určený na oxidáciu ketónov (cyklohexanón) → dokázaná „substrátová promiskuitnosť“

  3. Cyklohexanón → laktón

  4. N-hydroxylamín a nitróny → regioizoméry

  5. Laboratórna príprava nitrónov

  6. Mechanizmus oxidácie

  7. FAD-OOH ako oxidant

  8. CHMO-FAD

  9. FAD-OOH

  10. FAD-OOH + BnNHMe

  11. => FAD-OH + BnN(OH)Me

  12. Substráty a kinetické parametre

  13. Produkty oxidácií

  14. Bibliografia • S. Colona, V. Pironti, G. Carrea, P. Pasta, F. Zambianchi, Tetrahedron, 2004, 60, 569-575 • http://www.brenda-enzymes.info/php/result_flat.php4?ecno=1.14.13.22 • www.genome.jp/dbget-bin/www_bget?ec:1.14.13.22 • C. C. Ryerson, D. P. Ballou, C. Walsh, Biochemistry, 1982, 21 (11), 2644-2655 • Sheng Wu, J. P. Acevedo, M. T. Reetz, PNAS, 2010, 107 (7), 2775-2780 • J. A. Robi, J. R. Hwu, J. Org. Chem., 1985, 50, 5913 • S.-I. Murahashi, Angew. Chem. Int. Ed. Engl., 1995, 34, 2443-2458 • De Shong, JOC, 1985, 50, 2309 ; Tet. Lett., 1986, 27, 3979

  15. Bibliografia • A dissertation work of Zhan Xuanzhi: Catalytic mechanism of a flavin-dependent alkanesulfonate monooxygenase from Escherichia coli, Auburn, Alabama (USA), 9. august 2008 • Ellen Yeh, Sylvie Garneau, Christopher T. Walsh, PNAS, 2005, 102(11), 3960-3965 • S. Eswaramoorthy, J. B. Bonanno, S. K. Burley, S. Swaminathan, PNAS, 2006, 103(26), 9832-9837 - F. Zambianchi, P. Pasta, G. Carrea, S. Colonna, N. Gaggero, J. M. Woodley, Biotechnol. Bioeng., 2002, 78, 489- 496

  16. A toš je vše...

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