Organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity
Two β-cyclodextrin (β-CD) derivatives bearing steroid groups (1 and 2) were synthesized by the condensation of mono(6-aminoethylamino-6-deoxy)-β-CD with cholic acid and deoxycholic acid, respectively, and their original conformations and binding behavior to the organic anion of naphthalenesulfonate...
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sg-ntu-dr.10356-937972020-03-07T12:31:29Z Organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity Zhao, Yanli Zhang, Heng Yi Wang, Min Yu, Hong Mei Yang, Hua Liu, Yu School of Physical and Mathematical Sciences DRNTU::Science::Biological sciences::Biochemistry Two β-cyclodextrin (β-CD) derivatives bearing steroid groups (1 and 2) were synthesized by the condensation of mono(6-aminoethylamino-6-deoxy)-β-CD with cholic acid and deoxycholic acid, respectively, and their original conformations and binding behavior to the organic anion of naphthalenesulfonate derivatives were investigated by using 1H NMR spectroscopy and spectrofluorometric titration in combination with computational methods. The 2D NMR experiments reveal that the steroid groups attached to the β-CD rim could be deeply embedded in the β-CD cavity to form the intramolecular (for 1) or intermolecular (for 2) inclusion complexes in aqueous solution. Upon complexation with naphthalenesulfonate derivatives, modified β-CDs display two obviously different binding modes, that is, the competitive inclusion mode and the induced-fit inclusion mode, which is consistent with the results of molecular modeling study. The two modes and the strict size/shape fitting relationship between the hosts and guests reasonably explain the different binding behaviors and molecular selectivity of host β-CDs 1 and 2 toward the naphthalenesulfonate guests. Therefore, the cholic acid- or deoxycholic acid-modified β-CDs could effectively recognize the size/shape of guest molecules as compared with the parent β-CD, giving good molecular selectivity up to 24.9 for the disodium 2,6-naphthalenedisulfonate/disodium 1,5-naphthalenedisulfonate pair by the host 1. None of the above 2011-09-13T03:15:52Z 2019-12-06T18:45:41Z 2011-09-13T03:15:52Z 2019-12-06T18:45:41Z 2006 2006 Journal Article Zhao, Y. L., Zhang, H. Y., Wang, M., Yu, H. M., Yang, H., & Liu, Y. (2006). Organic Anion Recognition of Naphthalenesulfonates by Steroid-Modified β-Cyclodextrins: Enhanced Molecular Binding Ability and Molecular Selectivity. The Journal of Organic Chemistry, 71(16), 6010-6019. https://hdl.handle.net/10356/93797 http://hdl.handle.net/10220/7041 10.1021/jo060677q 159723 en Journal of organic chemistry © 2006 American Chemical Society 10 p. |
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DRNTU::Science::Biological sciences::Biochemistry Zhao, Yanli Zhang, Heng Yi Wang, Min Yu, Hong Mei Yang, Hua Liu, Yu Organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity |
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Two β-cyclodextrin (β-CD) derivatives bearing steroid groups (1 and 2) were synthesized by the condensation of mono(6-aminoethylamino-6-deoxy)-β-CD with cholic acid and deoxycholic acid, respectively, and their original conformations and binding behavior to the organic anion of naphthalenesulfonate derivatives were investigated by using 1H NMR spectroscopy and spectrofluorometric titration in combination with computational methods. The 2D NMR experiments reveal that the steroid groups attached to the β-CD rim could be deeply embedded in the β-CD cavity to form the intramolecular (for 1) or intermolecular (for 2) inclusion complexes in aqueous solution. Upon complexation with naphthalenesulfonate derivatives, modified β-CDs display two obviously different binding modes, that is, the competitive inclusion mode and the induced-fit inclusion mode, which is consistent with the results of molecular modeling study. The two modes and the strict size/shape fitting relationship between the hosts and guests reasonably explain the different binding behaviors and molecular selectivity of host β-CDs 1 and 2 toward the naphthalenesulfonate guests. Therefore, the cholic acid- or deoxycholic acid-modified β-CDs could effectively recognize the size/shape of guest molecules as compared with the parent β-CD, giving good molecular selectivity up to 24.9 for the disodium 2,6-naphthalenedisulfonate/disodium 1,5-naphthalenedisulfonate pair by the host 1. |
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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Zhao, Yanli Zhang, Heng Yi Wang, Min Yu, Hong Mei Yang, Hua Liu, Yu |
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Article |
author |
Zhao, Yanli Zhang, Heng Yi Wang, Min Yu, Hong Mei Yang, Hua Liu, Yu |
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Zhao, Yanli |
title |
Organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity |
title_short |
Organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity |
title_full |
Organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity |
title_fullStr |
Organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity |
title_full_unstemmed |
Organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity |
title_sort |
organic anion recognition of naphthalenesulfonates by steroid-modified β-cyclodextrins : enhanced molecular binding ability and molecular selectivity |
publishDate |
2011 |
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https://hdl.handle.net/10356/93797 http://hdl.handle.net/10220/7041 |
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1681045644951683072 |