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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Molecular Diversity Preservation International (MDPI)
2011
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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. |
format | Online Article Text |
id | pubmed-3155374 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | Molecular Diversity Preservation International (MDPI) |
record_format | MEDLINE/PubMed |
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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