Stabilization of calcium- and terbium-carboxylate bonds by NH...O hydrogen bonds in a mononuclear complex: a functional model of the active site of calcium-binding proteins

Inorganic Chemistry
Akira OnodaYoshi Okamoto

Abstract

Novel benzoic acid ligands with bulky amide groups at the ortho position, 2,6-(MeCONH)(2)C(6)H(3)CO(2)H (1) and 2,6-(t-BuCONH)(2)C(6)H(3)CO(2)H (2), and their tris- and tetrakis(carboxylate) complexes with Ca(II) and Tb(III) ions, (NEt(4))(2)[Ca(II)[O(2)C-2,6-(t-BuCONH)(2)C(6)H(3)](4)] (4), [Tb[O(2)C-2,6-(t-BuNHCO)(2)C(6)H(3)](3)(H(2)O)(3)]] (5), and (NMe)(4)[Tb[O(2)C-2,6-(t-BuNHCO)(2)C(6)H(3)](4)(thf)] (6), were synthesized. The formation of the NH...O hydrogen bonds between the amide NH and carboxylate for 2, (NEt(4))[2,6-(t-BuCONH)(2)C(6)H(3)CO(2)] (3), and 4 was determined by (1)H NMR spectroscopy in solution and in the solid state (CRAMPS, IR). The ligand exchange reactions were attempted between 4 and a large excess of 2,4,6- Me(3)C(6)H(3)CO(2)H in chloroform-d solution; however, exchange reaction did not take place, indicating that the Ca(II) ions bound strongly to the carboxylate in 4. The Ca(II) ion binding properties with the benzoate derivatives were also examined using Tb(III) ion as a fluorescence probe. These results indicate that the NH...O hydrogen bonding between the amide NH and the oxygen atom of the carboxylate contributes to strong Ca(II) binding and prevents the dissociation of the calcium-carboxylate bond...Continue Reading

References

Sep 5, 1978·Journal of Molecular Biology·J SowadskiR H Kretsinger
Oct 5, 1988·Journal of Molecular Biology·O Herzberg, M N James
Jan 1, 1984·Progress in Biophysics and Molecular Biology·E N Baker, R E Hubbard
Dec 30, 1998·Journal of the American Chemical Society·John R HagadornWilliam B Tolman

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Citations

Sep 13, 2013·Inorganic Chemistry·Taka-aki Okamura, Junko Nakagawa
Nov 3, 2016·Chemistry : a European Journal·Kamran T Mahmudov, Armando J L Pombeiro
Mar 26, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Taka-aki OkamuraKiyotaka Onitsuka
Jul 5, 2018·Journal of Enzyme Inhibition and Medicinal Chemistry·Maria Paola GiovannoniClaudia Vergelli
Aug 14, 2008·Organic & Biomolecular Chemistry·Takashi MatsuhiraNorikazu Ueyama
Mar 25, 2006·Organic & Biomolecular Chemistry·Takashi MatsuhiraNorikazu Ueyama

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