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 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.
López-Méndez
Blanca
B
Departamento de Ciencia de Proteínas, Centro de Investigaciones Biológicas, CSIC, Ramiro de Maeztu 9, Madrid, Spain.
Jia
Cai
C
Zhang
Yongmin
Y
Zhang
Li-He
LH
Sinaÿ
Pierre
P
Jiménez-Barbero
Jesús
J
Sollogoub
Matthieu
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D010100:Oxygen / Q000737:chemistry; D013395:Sucrose / Q000031:analogs & derivatives* / Q000737:chemistry
D013395:Sucrose; D010100:Oxygen