Hemicarbasucrose: Turning off the Exoanomeric Effect Induces Less Flexibility
Hemicarbasucrose, a close congener of sucrose in which the endocyclic oxygen atom of the glucose moiety is replaced by a methylene group was synthesized for the first time. The conformational behaviour of hemicarbasucrose was studied by a combination of molecular mechanics and NMR spectroscopy (J an...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2008-01, Vol.3 (1), p.51-58 |
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| creator | López-Méndez, Blanca Jia , Cai Zhang, Yongmin Zhang, Li-He Sinaÿ, Pierre Jiménez-Barbero, Jesús Sollogoub, Matthieu |
| description | Hemicarbasucrose, a close congener of sucrose in which the endocyclic oxygen atom of the glucose moiety is replaced by a methylene group was synthesized for the first time. The conformational behaviour of hemicarbasucrose was studied by a combination of molecular mechanics and NMR spectroscopy (J and NOE data). It was shown that the carbadisaccharide populates two distinct conformational families in solution, the normal syn‐ψ conformation, which is the predominating conformation of the parent natural O‐glycoside, and the anti‐ψ conformation, which has not been detected for the O‐disaccharide. Interestingly, the hemicarbasucrose is less flexible than its natural congener.
Sweet or semisweet? The synthesis and conformation analysis of the carbapyranoside analogue of sucrose (see picture of hemicarbasucrose) shows that replacement of the oxygen atom of the glucose moiety apparently induces the absence of an exoanomeric effect and, paradoxically, results in the rigidification of the structure. |
| doi_str_mv | 10.1002/asia.200700281 |
| format | Article |
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Sweet or semisweet? The synthesis and conformation analysis of the carbapyranoside analogue of sucrose (see picture of hemicarbasucrose) shows that replacement of the oxygen atom of the glucose moiety apparently induces the absence of an exoanomeric effect and, paradoxically, results in the rigidification of the structure.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.200700281</identifier><identifier>PMID: 18033715</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Carbohydrate Conformation ; Carbohydrate Sequence ; carbohydrates ; conformation analysis ; glycomimetics ; Magnetic Resonance Spectroscopy ; molecular modeling ; Molecular Sequence Data ; NMR spectroscopy ; Oxygen - chemistry ; Sucrose - analogs & derivatives ; Sucrose - chemistry</subject><ispartof>Chemistry, an Asian journal, 2008-01, Vol.3 (1), p.51-58</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4871-2ff8c7c1ccc9357489f014dc8d6108a9c8e7c47dba2e3db1fcc015748e314d4c3</citedby><cites>FETCH-LOGICAL-c4871-2ff8c7c1ccc9357489f014dc8d6108a9c8e7c47dba2e3db1fcc015748e314d4c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fasia.200700281$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.200700281$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27922,27923,45572,45573</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18033715$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>López-Méndez, Blanca</creatorcontrib><creatorcontrib>Jia , Cai</creatorcontrib><creatorcontrib>Zhang, Yongmin</creatorcontrib><creatorcontrib>Zhang, Li-He</creatorcontrib><creatorcontrib>Sinaÿ, Pierre</creatorcontrib><creatorcontrib>Jiménez-Barbero, Jesús</creatorcontrib><creatorcontrib>Sollogoub, Matthieu</creatorcontrib><title>Hemicarbasucrose: Turning off the Exoanomeric Effect Induces Less Flexibility</title><title>Chemistry, an Asian journal</title><addtitle>Chemistry - An Asian Journal</addtitle><description>Hemicarbasucrose, a close congener of sucrose in which the endocyclic oxygen atom of the glucose moiety is replaced by a methylene group was synthesized for the first time. The conformational behaviour of hemicarbasucrose was studied by a combination of molecular mechanics and NMR spectroscopy (J and NOE data). It was shown that the carbadisaccharide populates two distinct conformational families in solution, the normal syn‐ψ conformation, which is the predominating conformation of the parent natural O‐glycoside, and the anti‐ψ conformation, which has not been detected for the O‐disaccharide. Interestingly, the hemicarbasucrose is less flexible than its natural congener.
Sweet or semisweet? The synthesis and conformation analysis of the carbapyranoside analogue of sucrose (see picture of hemicarbasucrose) shows that replacement of the oxygen atom of the glucose moiety apparently induces the absence of an exoanomeric effect and, paradoxically, results in the rigidification of the structure.</description><subject>Carbohydrate Conformation</subject><subject>Carbohydrate Sequence</subject><subject>carbohydrates</subject><subject>conformation analysis</subject><subject>glycomimetics</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>molecular modeling</subject><subject>Molecular Sequence Data</subject><subject>NMR spectroscopy</subject><subject>Oxygen - chemistry</subject><subject>Sucrose - analogs & derivatives</subject><subject>Sucrose - chemistry</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkD1v2zAQhomiRb7XjoGmbnJ4oixS2VzXcQzY7VAHyUZQp2PKRh8pKSH2v48MG263TncHPO8L3MPYZ-Aj4Dy5McGZUcK5HA4FH9gZqAziVMLTx-OeqFN2HsJvzscJz9UJOwXFhZAwPmOre6odGl-Y0KNvA91G6943rnmOWmuj7hdFs01rmrYm7zCaWUvYRYum7JFCtKQQoruKNq5wleu2l-yTNVWgq8O8YA93s_X0Pl7-mC-mk2WMqZIQJ9YqlAiImIuxTFVuOaQlqjIDrkyOiiSmsixMQqIswCJy2HEkBixFccG-7Htfffunp9Dp2gWkqjINtX3QkkOWZiAHcLQHd78FT1a_elcbv9XA9U6g3gnUR4FD4PrQ3Bc1lX_xg7EByPfAm6to-586Pfm5mPxbHu-zLnS0OWaNf9GZFHKsH7_P9VfBV5BPV_qbeAd4yIxB</recordid><startdate>20080104</startdate><enddate>20080104</enddate><creator>López-Méndez, Blanca</creator><creator>Jia , Cai</creator><creator>Zhang, Yongmin</creator><creator>Zhang, Li-He</creator><creator>Sinaÿ, Pierre</creator><creator>Jiménez-Barbero, Jesús</creator><creator>Sollogoub, Matthieu</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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>20080104</creationdate><title>Hemicarbasucrose: Turning off the Exoanomeric Effect Induces Less Flexibility</title><author>López-Méndez, Blanca ; Jia , Cai ; Zhang, Yongmin ; Zhang, Li-He ; Sinaÿ, Pierre ; Jiménez-Barbero, Jesús ; Sollogoub, Matthieu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4871-2ff8c7c1ccc9357489f014dc8d6108a9c8e7c47dba2e3db1fcc015748e314d4c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Carbohydrate Conformation</topic><topic>Carbohydrate Sequence</topic><topic>carbohydrates</topic><topic>conformation analysis</topic><topic>glycomimetics</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>molecular modeling</topic><topic>Molecular Sequence Data</topic><topic>NMR spectroscopy</topic><topic>Oxygen - chemistry</topic><topic>Sucrose - analogs & derivatives</topic><topic>Sucrose - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>López-Méndez, Blanca</creatorcontrib><creatorcontrib>Jia , Cai</creatorcontrib><creatorcontrib>Zhang, Yongmin</creatorcontrib><creatorcontrib>Zhang, Li-He</creatorcontrib><creatorcontrib>Sinaÿ, Pierre</creatorcontrib><creatorcontrib>Jiménez-Barbero, Jesús</creatorcontrib><creatorcontrib>Sollogoub, Matthieu</creatorcontrib><collection>Istex</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>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>López-Méndez, Blanca</au><au>Jia , Cai</au><au>Zhang, Yongmin</au><au>Zhang, Li-He</au><au>Sinaÿ, Pierre</au><au>Jiménez-Barbero, Jesús</au><au>Sollogoub, Matthieu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hemicarbasucrose: Turning off the Exoanomeric Effect Induces Less Flexibility</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chemistry - An Asian Journal</addtitle><date>2008-01-04</date><risdate>2008</risdate><volume>3</volume><issue>1</issue><spage>51</spage><epage>58</epage><pages>51-58</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>Hemicarbasucrose, a close congener of sucrose in which the endocyclic oxygen atom of the glucose moiety is replaced by a methylene group was synthesized for the first time. The conformational behaviour of hemicarbasucrose was studied by a combination of molecular mechanics and NMR spectroscopy (J and NOE data). It was shown that the carbadisaccharide populates two distinct conformational families in solution, the normal syn‐ψ conformation, which is the predominating conformation of the parent natural O‐glycoside, and the anti‐ψ conformation, which has not been detected for the O‐disaccharide. Interestingly, the hemicarbasucrose is less flexible than its natural congener.
Sweet or semisweet? The synthesis and conformation analysis of the carbapyranoside analogue of sucrose (see picture of hemicarbasucrose) shows that replacement of the oxygen atom of the glucose moiety apparently induces the absence of an exoanomeric effect and, paradoxically, results in the rigidification of the structure.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>18033715</pmid><doi>10.1002/asia.200700281</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Carbohydrate Conformation Carbohydrate Sequence carbohydrates conformation analysis glycomimetics Magnetic Resonance Spectroscopy molecular modeling Molecular Sequence Data NMR spectroscopy Oxygen - chemistry Sucrose - analogs & derivatives Sucrose - chemistry |
| title | Hemicarbasucrose: Turning off the Exoanomeric Effect Induces Less Flexibility |
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