Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 3, Issue 1, Pages 51-58Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200700281
Keywords
carbohydrates; conformation analysis; glycomimetics; molecular modeling; NMR spectroscopy
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Hemicarbasucrose, a close congener of sucrose in which the endo-cyclic 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-psi conformation, which is the predominating conformation of the parent natural O-glycoside, and the anti-V conformation, which has not been detected for the O-disaccharide. Interestingly, the hemicarbasucrose is less flexible than its natural congener.
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