Tyrosinase-like reactivity in a Cu2III(μ-O)2e species

被引:60
作者
Company, Anna [3 ]
Palavicini, Sara [4 ]
Garcia-Bosch, Isaac [3 ]
Mas-Balleste, Ruben [1 ,2 ]
Que, Lawrence, Jr. [1 ,2 ]
Rybak-Akimova, Elena V. [5 ]
Casella, Luigi [4 ]
Ribas, Xavi [3 ]
Costas, Miquel [3 ]
机构
[1] Univ Minnesota, Ctr Metals Biocatalysis, Minneapolis, MN 55455 USA
[2] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
[3] Univ Girona, Dept Quim, Girona 17071, Spain
[4] Univ Pavia, Dept Gen Chem, I-27100 Pavia, Italy
[5] Tufts Univ, Dept Chem, Medford, MA 02155 USA
关键词
D O I
10.1002/chem.200800229
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
A study was conducted to demonstrate a bis(μ-oxo)dicopper(III) species that binds and ortho-hydroxylates phenolates for reactivity of tyrosinase. The study characterized a metastable species from the low-temperature reaction of sodium p-chloro-phenolate (p-Cl-C6H4ONa) with a bis(μ-oxo)dicopper(III) species. The study found that the addition of 10 equivalents of the sodium salt of p-chlorophenol at -90°C can cause bleaching of the spectral features. High performance liquid chromatography (HPLC) analysis showed that 4-chlorocatechol was formed in 76% yield. The study used UV/UVis monitoring for reaction in acetone to determine the initial features to the bis(μ-oxo) species and found that these features disappear after phenolate addition. The study observed that the activation parameters for the monophenolase reaction catalyzed by tyrosinase.
引用
收藏
页码:3535 / 3538
页数:4
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