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2008:
López-Méndez Blanca; Jia Cai; Zhang Yongmin; Zhang Li-He; Sinaÿ Pierre; Jiménez-Barbero Jesús; Sollogoub Matthieu
Hemicarbasucrose: turning off the exoanomeric effect induces less flexibility.
Chemistry, an Asian journal 2008;
3(
1):.
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-psi conformation, which is the predominating conformation of the parent natural O-glycoside, and the anti-psi conformation, which has not been detected for the O-disaccharide. Interestingly, the hemicarbasucrose is less flexible than its natural congener.
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