Abstract
The aim of this work was to construct chemical models for selective hydrolysis of phosphate monoesters in order to elucidate the role of metal ions in the hydrolytic mechanisms and to develop artificial enzymes for practical applications. A dinuclear copper(II) complex of a cyclohexane-based polyamino polyalcohol provided a selective and by far the highest rate acceleration among the transition metal complexes containing divalent metal ions for the hydrolysis of a phosphate monoester.
Highlights
Dinuclear complexes as chemical models of phosphodiesterases have attracted great interest in the last years in order to elucidate the role of metal ions in the hydrolytic mechanisms,[1] and to develop artificial nucleases,[2] which may have important applications in biotechnology and chemotherapy
Much less attention has been paid to the selective hydrolysis of phosphate monoesters by metal complexes, their hydrolysis is of central importance to the biochemistry of living cells
Since the dinuclear Cu2H–3tdci complex promoted very efficiently the hydrolysis of the phosphodiester bis(4-nitrophenyl)phosphate (BNPP),5b first we tested the kinetic activity of the copper(II)-tmci complexes using BNPP as substrate
Summary
Dinuclear complexes as chemical models of phosphodiesterases have attracted great interest in the last years in order to elucidate the role of metal ions in the hydrolytic mechanisms,[1] and to develop artificial nucleases,[2] which may have important applications in biotechnology and chemotherapy. That the dinuclear copper(II) and zinc(II) complexes of 1,3,5-trideoxy-1,3,5-tris(dimethylamino)-cis-inositol (tdci) provide outstanding rate acceleration for the hydrolysis of the activated phosphodiester bis(4-nitrophenyl)-phosphate (BNPP),5b nucleoside 2’,3’-cyclic monophosphates and dinucleoside monophosphates.[12] The dinuclear copper(II) complex possesses considerably lower efficiency toward the hydrolysis of the phosphate monoester 4-nitrophenyl phosphate (NPP).5b The related monomethylated ligand 1,3,5-trideoxy-1,3,5-tris(methylamino)-cis-inositol (tmci) is less rigidly preorganized than tdci, due to the decreased intraligand repulsions between the methylamino groups, which may strongly influence the properties of their metal complexes.
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