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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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dc.contributor.authorJianping Wang-
dc.contributor.authorYoonjung Jang-
dc.contributor.authorJayshree K. Khedkar-
dc.contributor.authorJin Young Koo-
dc.contributor.authorYonghwi Kim-
dc.contributor.authorChang Jun Lee-
dc.contributor.authorYoung Min Rhee-
dc.contributor.authorKimoon Kim-
dc.date.available2017-01-20T08:31:23Z-
dc.date.created2017-01-17-
dc.date.issued2016-10-
dc.identifier.issn0947-6539-
dc.identifier.urihttps://pr.ibs.re.kr/handle/8788114/3261-
dc.description.abstractCucurbit[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-
dc.languageENG-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.titleHow Does Solvation Affect the Binding of Hydrophilic Amino Saccharides to Cucurbit[7]uril with Exceptional Anomeric Selectivity?-
dc.typeArticle-
dc.type.rimsA-
dc.identifier.wosid000386795700030-
dc.identifier.scopusid2-s2.0-84987851378-
dc.date.tcdate2018-10-01-
dc.date.scptcdate2018-10-01-
dc.subject.keywordanomeric selectivity · host–guest systems · molecular dynamics · solvent effects · supramolecular chemistry-
dc.contributor.affiliatedAuthorJianping Wang-
dc.contributor.affiliatedAuthorYoonjung Jang-
dc.contributor.affiliatedAuthorJayshree K. Khedkar-
dc.contributor.affiliatedAuthorYonghwi Kim-
dc.contributor.affiliatedAuthorChang Jun Lee-
dc.contributor.affiliatedAuthorYoung Min Rhee-
dc.contributor.affiliatedAuthorKimoon Kim-
dc.identifier.bibliographicCitationCHEMISTRY-A EUROPEAN JOURNAL, v.22, no.44, pp.15791 - 15799-
dc.description.scptc0-
Appears in Collections:
Center for Self-assembly and Complexity(복잡계 자기조립 연구단) > Journal Papers (저널논문)
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