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Crystals 2013, 3(2), 306-314; doi:10.3390/cryst3020306

Glycine Betaine Recognition through Cation−π Interactions in Crystal Structures of Glycine Betaine Complexes with C-Ethyl-pyrogallol[4]arene and C-Ethyl-resorcin[4]arene as Receptors

1
Department of Environmental and Life Sciences, Toyohashi University of Technology, Hibarigaoka 1-1, Tempakucho, Toyohashi, Aichi 441-8580, Japan
2
Department of Materials Science, Toyohashi University of Technology, Hibarigaoka 1-1, Tempakucho, Toyohashi, Aichi 441-8580, Japan
*
Authors to whom correspondence should be addressed.
Received: 21 January 2013 / Revised: 7 March 2013 / Accepted: 25 March 2013 / Published: 16 April 2013
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Abstract

The glycine betaine (betaine), interacts with several types of proteins with diverse structures in vivo, and in the contact regions, the aromatic rings of protein residues are frequently found beside the trimethylammonium group of betaine, implying the importance of the cation−π interactions in recognition of this molecule. The crystal structures determined by X-ray crystallography of the complexes of betaine and C-ethyl-pyrogallol[4]arene (pyrogallol cyclic tetramer: PCT) and betaine and C-ethyl-resorcin[4]arene (resorcinol cyclic tetramer: RCT) mimic the conformations of betaine and protein complexes and show that the clathrate conformations are retained by the cation−π interactions. The difference of the conformation feature of betaine in the Protein Data Bank and in the Cambridge Structural Database was found by chance during the research and analyzed with the torsion angles. View Full-Text
Keywords: betaine; cation−π interactions; trimethylammonium group; aromatic rings; probable conformations betaine; cation−π interactions; trimethylammonium group; aromatic rings; probable conformations
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Fujisawa, I.; Aoki, K. Glycine Betaine Recognition through Cation−π Interactions in Crystal Structures of Glycine Betaine Complexes with C-Ethyl-pyrogallol[4]arene and C-Ethyl-resorcin[4]arene as Receptors. Crystals 2013, 3, 306-314.

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