Nicotinamide‐Dependent Ene Reductases as Alternative Biocatalysts for the Reduction of Activated Alkenes
作者： Katharina Durchschein , Silvia Wallner , Peter Macheroux , Wilfried Schwab , Thorsten Winkler
关键词:
摘要: Four NAD(P)H-dependent non-flavin ene reductases have been investigated for their ability to reduce activated C=C bonds in an asymmetric fashion by using 20 structurally diverse substrates. In comparison with flavin-dependent Old Yellow Enzyme homologues, a higher degree of electronic activation was required, because the best activities were obtained enals and nitroalkenes rather than enones carboxylic esters. Although FaEO from Fragaria x ananassa (strawberry) its homologue SlEO Solanum lycopersicum (tomato) exhibited narrow substrate spectrum, progesterone 5β-reductase (At5β-StR) Arabidopsis thaliana (thale cress) leukotriene B4 12-hydroxydehydrogenase (LTB4DH/PGR) Rattus norvegicus (rat) appear be promising candidates, particular bioreduction open-chain enals, α,β-unsaturated γ-butyrolactones. Competing nitro reduction non-enzymatic Weitz–Scheffer epoxidation largely suppressed.
elsevier.com
sci-hub.se 参考文章(41)
Harald S. Hansen, [26] Purification and assay of 15-ketoprostaglandin Δ13-reductase from bovine lung Methods in Enzymology. ,vol. 86, pp. 156- 163 ,(1982) , 10.1016/0076-6879(82)86186-7
Toshiko Yamamoto, Takehiko Yokomizo, Akihide Nakao, Takashi Izumi, Takao Shimizu, Immunohistochemical localization of guinea‐pig leukotriene B4 12‐hydroxydehydrogenase/15‐ketoprostaglandin 13‐reductase FEBS Journal. ,vol. 268, pp. 6105- 6113 ,(2001) , 10.1046/J.0014-2956.2001.02462.X
Jun’ichi Mano, Elena Babiychuk, Enric Belles-Boix, Jun Hiratake, Akira Kimura, Dirk Inzé, Sergei Kushnir, Kozi Asada, A novel NADPH:diamide oxidoreductase activity in Arabidopsis thaliana P1 ζ-crystallin. FEBS Journal. ,vol. 267, pp. 3661- 3671 ,(2000) , 10.1046/J.1432-1327.2000.01398.X
T. Yokomizo, T. Izumi, T. Takahashi, T. Kasama, Y. Kobayashi, F. Sato, Y. Taketani, T. Shimizu, Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase. Journal of Biological Chemistry. ,vol. 268, pp. 18128- 18135 ,(1993) , 10.1016/S0021-9258(17)46820-7
Clary B. Clish, Bruce D. Levy, Nan Chiang, Hsin-Hsiung Tai, Charles N. Serhan, Oxidoreductases in Lipoxin A4 Metabolic Inactivation A NOVEL ROLE FOR 15-OXOPROSTAGLANDIN 13-REDUCTASE/LEUKOTRIENE B4 12-HYDROXYDEHYDROGENASE IN INFLAMMATION Journal of Biological Chemistry. ,vol. 275, pp. 25372- 25380 ,(2000) , 10.1074/JBC.M002863200
Katharina Durchschein, Bianca Ferreira-da Silva, Silvia Wallner, Peter Macheroux, Wolfgang Kroutil, Silvia Maria Glueck, Kurt Faber, The flavoprotein-catalyzed reduction of aliphatic nitro-compounds represents a biocatalytic equivalent to the Nef-reaction Green Chemistry. ,vol. 12, pp. 616- 619 ,(2010) , 10.1039/B922691E
Mélanie Hall, Clemens Stueckler, Heidemarie Ehammer, Eva Pointner, Gustav Oberdorfer, Karl Gruber, Bernard Hauer, Rainer Stuermer, Wolfgang Kroutil, Peter Macheroux, Kurt Faber, Asymmetric Bioreduction of CC Bonds using Enoate Reductases OPR1, OPR3 and YqjM: Enzyme‐Based Stereocontrol Advanced Synthesis & Catalysis. ,vol. 350, pp. 411- 418 ,(2008) , 10.1002/ADSC.200700458
Jennifer Munkert, Peter Bauer, Edyta Burda, Frieder Müller-Uri, Wolfgang Kreis, Progesterone 5β-reductase of Erysimum crepidifolium: cDNA cloning, expression in Escherichia coli, and reduction of enones with the recombinant protein Phytochemistry. ,vol. 72, pp. 1710- 1717 ,(2011) , 10.1016/J.PHYTOCHEM.2011.06.007
Dorothée Klein, Barbara Fink, Beate Arold, Wolfgang Eisenreich, Wilfried Schwab, Functional characterization of enone oxidoreductases from strawberry and tomato fruit. Journal of Agricultural and Food Chemistry. ,vol. 55, pp. 6705- 6711 ,(2007) , 10.1021/JF071055O
Clemens Stueckler, Tamara C. Reiter, Nina Baudendistel, Kurt Faber, Nicotinamide-independent asymmetric bioreduction of CC-bonds via disproportionation of enones catalyzed by enoate reductases. Tetrahedron. ,vol. 66, pp. 663- 667 ,(2010) , 10.1016/J.TET.2009.11.065