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• W2016200531 abstract "Glyoxalase II enzymes catalyze the hydrolysis of a thioester substrate and have been found to coordinate a variety of dimetal combinations, including Fe(III)Zn(II), within the enzyme active site. Of relevance to these enzymes, the thioester hydrolysis reactivity of the Fe(III)Zn(II) compound [(BPBPMP)Fe(III)Zn(II)(μ-OAc)2]ClO4 (1) was evaluated in CH3CN/H2O (50:50; buffered) at 26.5 °C. Thioester hydrolysis in the absence and presence of 1 was monitored using 2H NMR by following the loss of the thioester −SCD3 signal. Two products are generated in the reaction involving the metal complex, D3CSSCD3 and CD3SH. Kinetic studies of this reaction as a function of pH revealed maximum rate above the pKa of a Zn−OH2 moiety of [(BPBPMP)Fe(III)(OH)(μ-OH)Zn(II)(OH2)]+, which forms from 1 in CH3CN/H2O (50:50). UV−vis and electron paramagnetic resonance (EPR) studies of a single turnover thioester hydrolysis reaction in the presence of 1 equiv of 1 at pH = 9.0 suggest that the thioester does not initially interact with the Fe(III) center, but that changes occur at this site over the course of the reaction. The formation of a Fe(III)−SCD3 moiety is proposed based on the observed D3CSSCD3 formation, which likely results from redox activity involving a iron(III) thiolate species. A mechanism for thioester hydrolysis is proposed involving initial coordination of the deprotonated α-hydroxy thioester to the zinc center followed by nucleophilic attack by a terminal Fe(III)−OH moiety and thiolate leaving group stabilization by the Fe(III) center. Overall, this study outlines a novel approach of using an aliphatic thioester substrate and 2H NMR to provide mechanistic insight into thioester hydrolysis involving an Fe(III)Zn(II) complex of relevance to glyoxalase II." @default.
• W2016200531 created "2016-06-24" @default.
• W2016200531 creator A5002560985 @default.
• W2016200531 creator A5027046803 @default.
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• W2016200531 date "2009-10-14" @default.
• W2016200531 modified "2023-09-29" @default.
• W2016200531 title "Thioester Hydrolysis Reactivity of an Fe(III)Zn(II) Complex" @default.
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• W2016200531 doi "https://doi.org/10.1021/ic901890d" @default.
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