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Inorganic–Organic Calcium Carbonate Composite of Synthetic Polymer Ligands with an Intramolecular NH···O Hydrogen Bond

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Biomineralization II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 271))

Abstract

Amide NH prelocating in the vicinity of a carboxylic acid group shifts the pK a of carboxylic acid to a lower value. A carboxylate anion is stabilized by NH⋯O hydrogen bond under hydrophobic conditions. In the case of Ca carboxylate complex, the decrease of the pK a value increases a formation constant involving the protonation process of carboxylic acid. In addition, the NH⋯O hydrogen bond controls the covalent character of the Ca–O bond for a totally neutral complex that possesses a shortening Ca–O bond distance. Both factors contribute to a strong binding of polycarboxylate on the surface of CaCO3 crystals. The polycarboxylate ligands with a NH⋯O hydrogen bond give nanosized vaterite crystals and are located on the surface of the vaterite agglomerate. The deprotonation of some carboxylic acids leads to conformational change in Asp-X-Gly tripeptides, partially amidated Kemp's acid and monoamidated maleate. Conformational switching between stabilized and activated forms for carboxylate affords an unusual crystal growth of calcite even if one of the conformers has a strong NH⋯O hydrogen bond.

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Authors and Affiliations

  1. Department of Macromolecular Science, Graduate School of Science, Osaka University, Toyonaka, 560-0043, Osaka, Japan

    Norikazu Ueyama, Kazuyuki Takahashi, Akira Onoda, Taka-aki Okamura & Hitoshi Yamamoto

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  1. Norikazu Ueyama
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  2. Kazuyuki Takahashi
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  3. Akira Onoda
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  4. Taka-aki Okamura
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Correspondence to Norikazu Ueyama .

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Kensuke Naka

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Ueyama, N., Takahashi, K., Onoda, A., Okamura, Ta., Yamamoto, H. (2006). Inorganic–Organic Calcium Carbonate Composite of Synthetic Polymer Ligands with an Intramolecular NH···O Hydrogen Bond. In: Naka, K. (eds) Biomineralization II. Topics in Current Chemistry, vol 271. Springer, Berlin, Heidelberg . https://doi.org/10.1007/128_2006_092

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