Regulation of Saccharide Binding with Basic Poly(ethynylpyridine)s by H+-Induced Helix Formation
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 g...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-11, Vol.127 (46), p.16189-16196 |
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| container_issue | 46 |
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| container_title | Journal of the American Chemical Society |
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| creator | Abe, Hajime Masuda, Nozomi Waki, Minoru Inouye, Masahiko |
| description | 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. |
| doi_str_mv | 10.1021/ja054134u |
| format | Article |
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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.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja054134u</identifier><identifier>PMID: 16287308</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Applied sciences ; Exact sciences and technology ; Hexoses - chemistry ; Molecular Structure ; Molecular Weight ; Organic polymers ; Physicochemistry of polymers ; Polymers - chemistry ; Properties and characterization ; Protons ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Solution and gel properties ; Spectrum Analysis ; Titrimetry ; Trifluoroacetic Acid - chemistry</subject><ispartof>Journal of the American Chemical Society, 2005-11, Vol.127 (46), p.16189-16196</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-4b2de895ff4d410f0e411c78897e658ff167b4e00ac3cf60a7ea238b7f7cba153</citedby><cites>FETCH-LOGICAL-a381t-4b2de895ff4d410f0e411c78897e658ff167b4e00ac3cf60a7ea238b7f7cba153</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja054134u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja054134u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17317680$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16287308$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abe, Hajime</creatorcontrib><creatorcontrib>Masuda, Nozomi</creatorcontrib><creatorcontrib>Waki, Minoru</creatorcontrib><creatorcontrib>Inouye, Masahiko</creatorcontrib><title>Regulation of Saccharide Binding with Basic Poly(ethynylpyridine)s by H+-Induced Helix Formation</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>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.</description><subject>Applied sciences</subject><subject>Exact sciences and technology</subject><subject>Hexoses - chemistry</subject><subject>Molecular Structure</subject><subject>Molecular Weight</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>Polymers - chemistry</subject><subject>Properties and characterization</subject><subject>Protons</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Solution and gel properties</subject><subject>Spectrum Analysis</subject><subject>Titrimetry</subject><subject>Trifluoroacetic Acid - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1v1DAQBmALgei2cOAPIF9AVChgx_FHj7SibFGBQkvFzUyccddL1tnaiWj-PYFddS-cRqN59Gr0EvKMszeclfztEpisuKiGB2TGZckKyUv1kMwYY2WhjRJ7ZD_n5bRWpeGPyR5XpdGCmRn5-Q1vhhb60EXaeXoJzi0ghQbpcYhNiDf0d-gX9BhycPSia8dX2C_GOLbrcVIh4mGm9Ujnr4uz2AwOGzrHNtzR0y6t_qU-IY88tBmfbucB-X76_upkXpx_-XB28u68AGF4X1R12aA5kt5XTcWZZ1hx7rQxRxqVNN5zpesKGQMnnFcMNEIpTK29djVwKQ7Iy03uOnW3A-berkJ22LYQsRuyVcYwKZme4OEGutTlnNDbdQorSKPlzP6t097XOdnn29ChXmGzk9v-JvBiCyA7aH2C6ELeOS24VoZNrti4kHu8u79D-mWVFlraq4tL--nrR_njuvpsr3e54LJddkOKU3f_efAPEWKYHw</recordid><startdate>20051123</startdate><enddate>20051123</enddate><creator>Abe, Hajime</creator><creator>Masuda, Nozomi</creator><creator>Waki, Minoru</creator><creator>Inouye, Masahiko</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20051123</creationdate><title>Regulation of Saccharide Binding with Basic Poly(ethynylpyridine)s by H+-Induced Helix Formation</title><author>Abe, Hajime ; Masuda, Nozomi ; Waki, Minoru ; Inouye, Masahiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-4b2de895ff4d410f0e411c78897e658ff167b4e00ac3cf60a7ea238b7f7cba153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Applied sciences</topic><topic>Exact sciences and technology</topic><topic>Hexoses - chemistry</topic><topic>Molecular Structure</topic><topic>Molecular Weight</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>Polymers - chemistry</topic><topic>Properties and characterization</topic><topic>Protons</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Solution and gel properties</topic><topic>Spectrum Analysis</topic><topic>Titrimetry</topic><topic>Trifluoroacetic Acid - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abe, Hajime</creatorcontrib><creatorcontrib>Masuda, Nozomi</creatorcontrib><creatorcontrib>Waki, Minoru</creatorcontrib><creatorcontrib>Inouye, Masahiko</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abe, Hajime</au><au>Masuda, Nozomi</au><au>Waki, Minoru</au><au>Inouye, Masahiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regulation of Saccharide Binding with Basic Poly(ethynylpyridine)s by H+-Induced Helix Formation</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-11-23</date><risdate>2005</risdate><volume>127</volume><issue>46</issue><spage>16189</spage><epage>16196</epage><pages>16189-16196</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>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.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16287308</pmid><doi>10.1021/ja054134u</doi><tpages>8</tpages></addata></record> |
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| subjects | Applied sciences Exact sciences and technology Hexoses - chemistry Molecular Structure Molecular Weight Organic polymers Physicochemistry of polymers Polymers - chemistry Properties and characterization Protons Pyridines - chemical synthesis Pyridines - chemistry Solution and gel properties Spectrum Analysis Titrimetry Trifluoroacetic Acid - chemistry |
| title | Regulation of Saccharide Binding with Basic Poly(ethynylpyridine)s by H+-Induced Helix Formation |
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