Zinc Complexes of Artificial Histidine-containing Dipeptides as Catalysts of Hydrolyses of p-Nitrophenyl Phosphates

Abstract

Zinc complexes of histidine-containing peptide derived from N,N′-dihistidylethylenediamine L1 and im-bzl-N,N″-dihistidyldiethylenetriamine L2 were designed and examined as catalysts for hydrolyses of bis(p-nitrophenyl)phosphate (BNPP) and p-nitrophenyl phosphate (NPP). The zinc complex of L1 was inactive and another L2 complex hydrolyzed efficiently BNPP and NPP: their pseudo-first-order rate constants are 1.1 × 10−5 s−1 and 2.1 × 10−5 s−1, respectively.

Zinc(II) tweezers containing artificial peptides mimicking the active site of phosphotriesterase: The catalyzed hydrolysis of the toxic organophosphate parathion

“…5.39 in His-Gly, 5.65 in His-Leu while this value is 5.87 in histidine [68,69]. Thus, L 2 has more basic imidazole nitrogens [70,71] because it lacks other aliphatic nitrogens, which is found in L 1 [60,[72][73][74], where the presence of these aliphatic amines makes the imidazol groups more acidic.…”

Copper(II) Complexes Containing N,N‐Donor Ligands and Dipeptides Act as Hydrolytic DNA‐Cleavage Agents

“…The hydrolysis of phosphodiesters by Zn complexes of His-containing peptides was also reported [21].…”

A promising structural zinc enzyme model for CO2 fixation and calcification

“…5-7 Recently, we have reported simulation of CO 2 hydration and phosphoester hydrolysis using structural zinc enzyme model complexes. [8][9][10][11][12][13][14][15][16][17] As a measure to cope with the possible global warming due to the greenhouse effect of CO 2 , our aim is to clarify how to fix and calcify CO 2 as CaCO 3 by synthesizing a zinc complex, which functionally mimics the active site of the nacrein protein in molluscs (Scheme 2).We have synthesized and characterized a new ligand, namely, N-{tris([2-[(1-methylbenzimidazol-2-yl)ethyl]-methyl]amino)-2-oxoethyl}iminodiacetic acid L (Scheme 3). The ligand was used to prepare a complex in which a Zn(II) ion is coordinated to three benzimidazole nitrogens.…”

“…[5][6][7] Recently, we have reported simulation of CO 2 hydration and phosphoester hydrolysis using structural zinc enzyme model complexes. [8][9][10][11][12][13][14][15][16][17] As a measure to cope with the possible global warming due to the greenhouse effect of CO 2 , our aim is to clarify how to fix and calcify CO 2 as CaCO 3 by synthesizing a zinc complex, which functionally mimics the active site of the nacrein protein in molluscs (Scheme 2).…”

“…1). In the pH range investigated (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), the ligand can bind four protons, presumably one at the tertiary amino group and three at the benzimidazole nitrogens. These step-wise protonation constants were determined, and are listed in Table 1.…”