title: Hemicarbasucrose: turning off the exoanomeric effect induces less flexibility.
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-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.
authors.affiliation: Departamento de Ciencia de Proteínas, Centro de Investigaciones Biológicas, CSIC, Ramiro de Maeztu 9, Madrid, Spain.
authors.forename: Blanca
authors.initials: B
authors.lastname: López-Méndez
authors.forename: Cai
authors.initials: C
authors.lastname: Jia
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
authors.forename: Li-He
authors.initials: LH
authors.lastname: Zhang
authors.forename: Pierre
authors.initials: P
authors.lastname: Sinaÿ
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
mesh_terms: 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
chemical_list: D013395:Sucrose; D010100:Oxygen