Development of bis(2-picolyl)amine-zinc chelates for imidazole receptors

被引：42

作者：

Routasalo, Taina ^{[1
]}

Helaja, Juho ^{[1
]}

Kavakka, Jari ^{[2
]}

Koskinen, Ari M. P. ^{[1
]}

机构：

[1] Aalto Univ, Dept Chem, Espoo 02015, Finland

[2] Univ Helsinki, Dept Chem, Organ Chem Lab, FIN-00014 Helsinki, Finland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 18期

关键词：

amines; N; O ligands; heterocycles; zinc; chelation;

D O I：

10.1002/ejoc.200700926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New phenyl and phenol bis(2-picolyl)amine (Dpa) derivatives have been synthesized in order to generate zinc chelates for imidazole anion receptors. Previously, binuclear phenolic zinc and copper chelates have shown affinity for pyrophosphate and guanidine anions, respectively. Herein we report significant imidazole affinity increasing from 2.38 x 10(6) to 2.90 x 10(7) for phenol-bridged binuclear zinc Dpa chelates, as evidenced by dynamic and titration H-1 NMR studies. Among the Dpa chelates investigated, the zinc-coordinated phenol group plays a crucial role in the mechanism of anion binding. Low-temperature H-1 NMR experiments suggest a sigma(v)-symmetric geometry for the imidazole chelate. Computational DFT studies at the B3LYP level of theory imply that imidazole binding displaces the phenol bridge between the zinc ions. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：3190 / 3199

页数：10

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[31] Synthetic analogues relevant to the structure and function of zinc enzymes [J].