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Enhanced Chiral Recognition by Cyclodextrin Dimers

In this article we investigate the effect of multivalency in chiral recognition. To this end, we measured the host-guest interaction of a β-cyclodextrin dimer with divalent chiral guests. We report the synthesis of carbohydrate-based water soluble chiral guests functionalized with two borneol, menth...

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Detalles Bibliográficos
Autores principales: Voskuhl, Jens, Schaepe, Kira, Ravoo, Bart Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International (MDPI) 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3155374/
https://www.ncbi.nlm.nih.gov/pubmed/21845101
http://dx.doi.org/10.3390/ijms12074637
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author Voskuhl, Jens
Schaepe, Kira
Ravoo, Bart Jan
author_facet Voskuhl, Jens
Schaepe, Kira
Ravoo, Bart Jan
author_sort Voskuhl, Jens
collection PubMed
description In this article we investigate the effect of multivalency in chiral recognition. To this end, we measured the host-guest interaction of a β-cyclodextrin dimer with divalent chiral guests. We report the synthesis of carbohydrate-based water soluble chiral guests functionalized with two borneol, menthol, or isopinocampheol units in either (+) or (−) configuration. We determined the interaction of these divalent guests with a β-cyclodextrin dimer using isothermal titration calorimetry. It was found that—in spite of a highly unfavorable conformation—the cyclodextrin dimer binds to guest dimers with an increased enantioselectivity, which clearly reflects the effect of multivalency.
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spelling pubmed-31553742011-08-15 Enhanced Chiral Recognition by Cyclodextrin Dimers Voskuhl, Jens Schaepe, Kira Ravoo, Bart Jan Int J Mol Sci Article In this article we investigate the effect of multivalency in chiral recognition. To this end, we measured the host-guest interaction of a β-cyclodextrin dimer with divalent chiral guests. We report the synthesis of carbohydrate-based water soluble chiral guests functionalized with two borneol, menthol, or isopinocampheol units in either (+) or (−) configuration. We determined the interaction of these divalent guests with a β-cyclodextrin dimer using isothermal titration calorimetry. It was found that—in spite of a highly unfavorable conformation—the cyclodextrin dimer binds to guest dimers with an increased enantioselectivity, which clearly reflects the effect of multivalency. Molecular Diversity Preservation International (MDPI) 2011-07-18 /pmc/articles/PMC3155374/ /pubmed/21845101 http://dx.doi.org/10.3390/ijms12074637 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0 This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Voskuhl, Jens
Schaepe, Kira
Ravoo, Bart Jan
Enhanced Chiral Recognition by Cyclodextrin Dimers
title Enhanced Chiral Recognition by Cyclodextrin Dimers
title_full Enhanced Chiral Recognition by Cyclodextrin Dimers
title_fullStr Enhanced Chiral Recognition by Cyclodextrin Dimers
title_full_unstemmed Enhanced Chiral Recognition by Cyclodextrin Dimers
title_short Enhanced Chiral Recognition by Cyclodextrin Dimers
title_sort enhanced chiral recognition by cyclodextrin dimers
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3155374/
https://www.ncbi.nlm.nih.gov/pubmed/21845101
http://dx.doi.org/10.3390/ijms12074637
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