Generalized Anomeric Effect in gem-Diamines: Stereoselective Synthesis of α-N-Linked Disaccharide Mimics
The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased in bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable α-N-linked azadisaccharide het...
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| Veröffentlicht in: | Organic letters 2009-08, Vol.11 (15), p.3306-3309 |
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| container_end_page | 3309 |
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| container_issue | 15 |
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| container_title | Organic letters |
| container_volume | 11 |
| creator | Sánchez-Fernández, Elena M Rísquez-Cuadro, Rocío Aguilar-Moncayo, Matilde García-Moreno, M. Isabel Mellet, Carmen Ortiz García Fernández, José M |
| description | The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased in bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable α-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase. |
| doi_str_mv | 10.1021/ol901125n |
| format | Article |
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Lett</addtitle><description>The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased in bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable α-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase.</description><subject>Diamines - chemistry</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Glucosamine - analogs & derivatives</subject><subject>Glucosamine - chemical synthesis</subject><subject>Glucosamine - chemistry</subject><subject>Isomaltose - chemical synthesis</subject><subject>Isomaltose - chemistry</subject><subject>Isomaltose - pharmacology</subject><subject>Maltose - chemical synthesis</subject><subject>Maltose - chemistry</subject><subject>Maltose - pharmacology</subject><subject>Molecular Mimicry</subject><subject>Oligo-1,6-Glucosidase - antagonists & inhibitors</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkLFOwzAQQC0EoqUw8APIC0IMAZ-TNAlb1ZaCVGAozJHjnqlL4hQ7QSp_xY_wTRi1KgvTnXRPT7pHyCmwK2AcrusyYwA8NnukCzEPg4TFfH-391mHHDm3ZB6KeXZIOpD1WT-NoUv0BA1aUepPnNOBqSu0WtKxUigbqg19xSoYaVFpg-6Gzhq0WDss_VV_IJ2tTbNApx2tFf3-Ch6DqTZv3jTSTki5EFbPkT7oSkt3TA6UKB2ebGePvNyOn4d3wfRpcj8cTAMRQtQEGeMKQpWwjIlUxVGiBOOR6nOEApjK_J4qxWPEKE0hUcBlkbAkSzIQGBYQ9sjFxruy9XuLrskr7SSWpTBYty5PwoiFkS_kycsNKW3tnEWVr6yuhF3nwPLfsPkurGfPtta2qHD-R25LeuB8Awjp8mXdWuOf_Ef0AwnPf4M</recordid><startdate>20090806</startdate><enddate>20090806</enddate><creator>Sánchez-Fernández, Elena M</creator><creator>Rísquez-Cuadro, Rocío</creator><creator>Aguilar-Moncayo, Matilde</creator><creator>García-Moreno, M. 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Lett</addtitle><date>2009-08-06</date><risdate>2009</risdate><volume>11</volume><issue>15</issue><spage>3306</spage><epage>3309</epage><pages>3306-3309</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased in bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable α-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>19606851</pmid><doi>10.1021/ol901125n</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2009-08, Vol.11 (15), p.3306-3309 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Diamines - chemistry Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Glucosamine - analogs & derivatives Glucosamine - chemical synthesis Glucosamine - chemistry Isomaltose - chemical synthesis Isomaltose - chemistry Isomaltose - pharmacology Maltose - chemical synthesis Maltose - chemistry Maltose - pharmacology Molecular Mimicry Oligo-1,6-Glucosidase - antagonists & inhibitors Stereoisomerism |
| title | Generalized Anomeric Effect in gem-Diamines: Stereoselective Synthesis of α-N-Linked Disaccharide Mimics |
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