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Jianping Wang
복잡계 자기조립 연구단
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How Does Solvation Affect the Binding of Hydrophilic Amino Saccharides to Cucurbit[7]uril with Exceptional Anomeric Selectivity?

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Title
How Does Solvation Affect the Binding of Hydrophilic Amino Saccharides to Cucurbit[7]uril with Exceptional Anomeric Selectivity?
Author(s)
Jianping Wang; Yoonjung Jang; Jayshree K. Khedkar; Jin Young Koo; Yonghwi Kim; Chang Jun Lee; Young Min Rhee; Kimoon Kim
Publication Date
2016-10
Journal
CHEMISTRY-A EUROPEAN JOURNAL, v.22, no.44, pp.15791 - 15799
Publisher
WILEY-V C H VERLAG GMBH
Abstract
Cucurbit[7]uril (CB[7]) is known to bind strongly to hydrophilic amino saccharide guests with exceptional aanomer selectivities under aqueous conditions. Single-crystal X-ray crystallography and computational methods were used to elucidate the reason behind this interesting phenomenon. The crystal structures of protonated galactosamine (GalN) and glucosamine (GluN) complexes confirm the inclusion of a anomers inside CB[7] and disclose the details of the host–guest binding. Whereas computed gas-phase structures agree with these crystal structures, gas-phase binding free energies show preferences for the b-anomer complexes over their a counterparts, in striking contrast to the experimental results under aqueous conditions. However, when the solvation effect is considered, the binding structures drastically change and the preference for the a anomers is recovered. The a anomers also tend to bind more tightly and leave less space in the CB[7] cavity toward inclusion of only one water molecule, whereas loosely bound b anomers leave more space toward accommodating two water molecules, with markedly different hydrogenbonding natures. Surprisingly, entropy seems to contribute significantly to both anomeric discrimination and binding. This suggests that of all the driving factors for the strong complexation of the hydrophilic amino saccharide guests, water mediation plays a crucial role in the anomer discrimination. (c) 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/3261
ISSN
0947-6539
Appears in Collections:
Center for Self-assembly and Complexity(복잡계 자기조립 연구단) > Journal Papers (저널논문)
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