A Potentially Polymerizable Heterodinuclear FeIIIZnII Purple Acid Phosphatase Mimic. Synthesis, Characterization, and Phosphate Ester Hydrolysis Studies

Abstract

An analogue of the purple acid phosphatase biomimetic 2-((bis(pyridin-2-ylmethyl)amino)methyl)-6-(((2-hydroxybenzyl)(pyridin-2-ylmethyl)amino)methyl)-4-methylphenol has been synthesized. The analogue, 2-((bis(pyridin-2-ylmethyl)amino)methyl)-6-(((2-hydroxy-4-(4-vinylbenzyloxy)benzyl)(pyridin-2-ylmethyl)amino)methyl)-4-methylphenol (H2BPBPMPV) possesses a pendant olefin suitable for copolymerization. Complexation with FeIII/ZnII resulted in the complex [FeIIIZnII(BPBPMPV)(CH3COO)2](ClO4), characterized with mass spectrometry, microanalysis, UV/vis, and IR spectrometry. The catalytic activity of the complex toward bis-(2,4-dinitrophenyl) phosphate was determined, resulting in Km of 4.1 ± 0.6 mM, with kcat 3.8 ± 0.2 × 10–3 s–1 and a bell-shaped pH–rate profile with pKa values of 4.31, 5.66, 8.96, the profile exhibiting residual activity above pH 9.5.