| Regulation of saccharide binding with basic poly(ethynylpyridine)s by H+-induced helix formation. | |
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MedLine Citation:
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PMID: 16287308 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A basic host polymer exhibiting pH-regulatable saccharide recognition has been investigated. Poly(m-ethynylpyridine) bearing dialkylamino groups forms helical complexes with saccharides to show induced circular dichroism (ICD). When trifluoroacetic acid was titrated on these complexes, the ICD was gradually enhanced until the amount of the acid reached ca. 0.5 molar equivalence versus the pyridine rings in the polymer, and further addition of the acid suppressed the ICD. The proper addition of the acid also increased the binding constants between the polymer and saccharides. These findings would be due to stabilization of the helical structure consisting of cisoid conformations for each of the adjacent pyridine pairs, which were caused by half-protonation of the pyridine rings. Computational analyses indicated that the pyridinium-pyridine dimeric structure prefers its cisoid conformation to its transoid one. |
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Authors:
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Hajime Abe; Nozomi Masuda; Minoru Waki; Masahiko Inouye |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 127 ISSN: 0002-7863 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2005 Nov |
Date Detail:
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Created Date: 2005-11-18 Completed Date: 2006-02-14 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 16189-96 Citation Subset: IM |
Affiliation:
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Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Toyama 930-0194, Japan. abeh@ms.toyama-mpu.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Hexoses
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chemistry* Molecular Structure Molecular Weight Polymers / chemistry* Protons* Pyridines / chemical synthesis, chemistry* Spectrum Analysis Titrimetry Trifluoroacetic Acid / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Hexoses; 0/Polymers; 0/Protons; 0/Pyridines; 0/ethynylpyridine; 76-05-1/Trifluoroacetic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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