Ethynylpyridine Polymers: Development of Polymeric Hosts for Saccharide Recognition
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- Abe Hajime
- Graduate School of Pharmaceutical Sciences, University of Toyama
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- Inouye Masahiko
- Graduate School of Pharmaceutical Sciences, University of Toyama
Bibliographic Information
- Other Title
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- 糖質を認識する高分子「エチニルピリジンポリマー」の開発
- トウシツ オ ニンシキ スル コウブンシ エチニルピリジン ポリマー ノ カイハツ
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Abstract
Saccharide recognition is one of the most attractive topics in host-guest and biomimicking chemistry. Herein we describe development of “meta-ethynylpyridine” poly-/oligomers as artificial hosts for saccharide recognition, which consist of 4-substituted pyridine rings linked 2,6-positions with acetylene bonds. When ethynylpyridine chains associate with a guest saccharide by multipoint hydrogen-bonds, a helical complex forms and its helicity is biassed by chirality of the guest saccharide. Substituents on the pyridine rings give additional characteristics such as solubility, amphiphilicity, basicity, and tautomeric ability. Amphiphilic polymer recognizes natural hexoses even in aqueous methanol. Basic and tautomeric ethynylpyridines switch their recognition ability by protonation and tautomerism, respectively. When a glycoside template is linked with ethynylpyridine oligomers covalently, the resulting helices are fixed by intramolecular association. Helical structure of azacrown-induced polymer is stabilized by collaboration with axial oligoammonium, accompanied with the improvement of glucoside recognition by pseudorotaxane formation between the crown and the oligoammonium.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 68 (2), 112-123, 2010
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001205311684096
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- NII Article ID
- 10026867805
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- NII Book ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BC3cXitlOhtr0%3D
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 10586923
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
- KAKEN
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- Abstract License Flag
- Disallowed