The first water-soluble bowl complex: molecular recognition of acetate by the biomimetic tris(imidazole) Zn(ii) system at pH 7.4Electronic supplementary information (ESI) available: Synthetic procedures, spectroscopic data and supplementary spectral data. See DOI: 10.1039/c4ob02514h
A supramolecular approach for modeling active sites of metallo-enzymes relies on the association of a metal ion bound to a tris(imidazole) core under the control of a cavity. One step further is the water-solubilization of the cavity-complex. Here, we describe the synthesis of a water-soluble bowl-l...
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| Main Authors | , , , |
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| Format | Journal Article |
| Language | English |
| Published |
04.03.2015
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| Abstract | A supramolecular approach for modeling active sites of metallo-enzymes relies on the association of a metal ion bound to a tris(imidazole) core under the control of a cavity. One step further is the water-solubilization of the cavity-complex. Here, we describe the synthesis of a water-soluble bowl-ligand that has been successively achieved through an 11-step strategy from resorcinol. First insights into its coordination properties in water show that it readily binds Zn(
ii
) at physiological pH and acts as a molecular receptor for the hydrophilic acetate guest ligand.
The bowl-shaped cavity-ligand based on resorcinarene has been successfully transposed into a water-soluble version that readily binds Zn(
ii
) and acetate at physiological pH. |
|---|---|
| AbstractList | A supramolecular approach for modeling active sites of metallo-enzymes relies on the association of a metal ion bound to a tris(imidazole) core under the control of a cavity. One step further is the water-solubilization of the cavity-complex. Here, we describe the synthesis of a water-soluble bowl-ligand that has been successively achieved through an 11-step strategy from resorcinol. First insights into its coordination properties in water show that it readily binds Zn(
ii
) at physiological pH and acts as a molecular receptor for the hydrophilic acetate guest ligand.
The bowl-shaped cavity-ligand based on resorcinarene has been successfully transposed into a water-soluble version that readily binds Zn(
ii
) and acetate at physiological pH. |
| Author | Reinaud, Olivia Rat, Stéphanie Bistri, Olivia Gout, Jérôme |
| AuthorAffiliation | Université Paris Descartes CNRS UMR 8601 Laboratoire de Chimie et de Biochimie pharmacologiques et toxicologiques Sorbonne Paris Cité |
| AuthorAffiliation_xml | – name: CNRS UMR 8601 – name: Sorbonne Paris Cité – name: Université Paris Descartes – name: Laboratoire de Chimie et de Biochimie pharmacologiques et toxicologiques |
| Author_xml | – sequence: 1 givenname: Stéphanie surname: Rat fullname: Rat, Stéphanie – sequence: 2 givenname: Jérôme surname: Gout fullname: Gout, Jérôme – sequence: 3 givenname: Olivia surname: Bistri fullname: Bistri, Olivia – sequence: 4 givenname: Olivia surname: Reinaud fullname: Reinaud, Olivia |
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| DOI | 10.1039/c4ob02514h |
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| Notes | Electronic supplementary information (ESI) available: Synthetic procedures, spectroscopic data and supplementary spectral data. See DOI 10.1039/c4ob02514h |
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| References_xml | – issn: 2007 publication-title: Biological Inorganic Chemistry, Structure and Reactivity doi: Bertini Gray Stiefel Valentine – issn: 2015 publication-title: Org. Biomol. Chem doi: Bistri Reinaud – issn: 1994 publication-title: Principles of Bioinorganic Chemistry doi: Lippard Berg |
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| Title | The first water-soluble bowl complex: molecular recognition of acetate by the biomimetic tris(imidazole) Zn(ii) system at pH 7.4Electronic supplementary information (ESI) available: Synthetic procedures, spectroscopic data and supplementary spectral data. See DOI: 10.1039/c4ob02514h |
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