Biomimetic modeling of copper complexes: a study of enantioselective catalytic oxidation on d-(+)-catechin and L-( - )-epicatechin with copper complexes.
作者： Francesco G. Mutti , Roberta Pievo , Maila Sgobba , Michele Gullotti , Laura Santagostini
DOI: 10.1155/2008/762029
关键词: Catalysis 、 Catalytic oxidation 、 Substrate (chemistry) 、 Medicinal chemistry 、 Reagent 、 Chemistry 、 Enantioselective synthesis 、 Organic chemistry 、 Catechol 、 Copper 、 Hydrazone
摘要: The biomimetic catalytic oxidations of the dinuclear and trinuclear copper(II) complexes versus two catechols, namely, -(+)-catechin -( )-epicatechin to give corresponding quinones are reported. unstable were trapped by nucleophilic reagent, 3-methyl-2-benzothiazolinone hydrazone (MBTH), have been calculated molar absorptivities different quinones. efficiency is moderate, as inferred kinetic constants, but exhibit significant enantio-differentiating ability towards albeit for complexes, this lower. In all cases, preferred enantiomeric substrate respect other catechol, because spatial disposition substrate.
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Marianne E. Cuff, Karen I. Miller, Kensal E. van Holde, Wayne A. Hendrickson, Crystal structure of a functional unit from Octopus hemocyanin. Journal of Molecular Biology. ,vol. 278, pp. 855- 870 ,(1998) , 10.1006/JMBI.1998.1647
Francesco G. Mutti, Giorgio Zoppellaro, Michele Gullotti, Laura Santagostini, Roberto Pagliarin, K. Kristoffer Andersson, Luigi Casella, Biomimetic Modelling of Copper Enzymes: Synthesis, Characterization, EPR Analysis and Enantioselective Catalytic Oxidations by a New Chiral Trinuclear Copper(II) Complex European Journal of Inorganic Chemistry. ,vol. 2009, pp. 554- 566 ,(2009) , 10.1002/EJIC.200800899
M. Jiménez-Atiénzar, J. Cabanes, F. Gandı́a-Herrero, F. Garcı́a-Carmona, Kinetic analysis of catechin oxidation by polyphenol oxidase at neutral pH Biochemical and Biophysical Research Communications. ,vol. 319, pp. 902- 910 ,(2004) , 10.1016/J.BBRC.2004.05.077
Ilja C. W. Arts, Betty van de Putte, Peter C. H. Hollman, Catechin Contents of Foods Commonly Consumed in The Netherlands. 2. Tea, Wine, Fruit Juices, and Chocolate Milk Journal of Agricultural and Food Chemistry. ,vol. 48, pp. 1752- 1757 ,(2000) , 10.1021/JF000026+
M. López-Serrano, A. Ros Barceló, Comparative Study of the Products of the Peroxidase-Catalyzed and the Polyphenoloxidase-Catalyzed (+)-Catechin Oxidation. Their Possible Implications in Strawberry (Fragaria × ananassa) Browning Reactions Journal of Agricultural and Food Chemistry. ,vol. 50, pp. 1218- 1224 ,(2002) , 10.1021/JF010902Z
Michele Gullotti, Laura Santagostini, Roberto Pagliarin, Alessandro Granata, Luigi Casella, Synthesis and characterization of new chiral octadentate nitrogen ligands and related copper(II) complexes as catalysts for stereoselective oxidation of catechols Journal of Molecular Catalysis A: Chemical. ,vol. 235, pp. 271- 284 ,(2005) , 10.1016/J.MOLCATA.2005.03.031
Enrico Monzani, Luigi Casella, Giorgio Zoppellaro, Michele Gullotti, Roberto Pagliarin, Raffaele P. Bonomo, Giovanni Tabbi, Giorgio Nardin, Lucio Randaccio, Synthetic models for biological trinuclear copper clusters. Trinuclear and binuclear complexes derived from an octadentate tetraamine-tetrabenzimidazole ligand Inorganica Chimica Acta. ,vol. 282, pp. 180- 192 ,(1998) , 10.1016/S0020-1693(98)00221-7
Maria Chiara Mimmi, Michele Gullotti, Laura Santagostini, Alberto Saladino, Luigi Casella, Enrico Monzani, Roberto Pagliarin, Stereoselective catalytic oxidations of biomimetic copper complexes with a chiral trinucleating ligand derived from 1,1-binaphthalene Journal of Molecular Catalysis A-chemical. ,vol. 204, pp. 381- 389 ,(2003) , 10.1016/S1381-1169(03)00320-0
Florence C. Richard-Forget, Frédéric A. Gauillard, Oxidation of Chlorogenic Acid, Catechins, and 4-Methylcatechol in Model Solutions by Combinations of Pear (Pyrus communis Cv. Williams) Polyphenol Oxidase and Peroxidase: A Possible Involvement of Peroxidase in Enzymatic Browning† Journal of Agricultural and Food Chemistry. ,vol. 45, pp. 2472- 2476 ,(1997) , 10.1021/JF970042F
Manisha Gupta, Pavan Mathur, Ray J. Butcher, Synthesis, crystal structure, spectral studies, and catechol oxidase activity of trigonal bipyramidal Cu(II) complexes derived from a tetradentate diamide bisbenzimidazole ligand. Inorganic Chemistry. ,vol. 40, pp. 878- 885 ,(2001) , 10.1021/IC000313V