title: Glycosidic bond hydrolysis in septanosides: a comparison of mono-, di-, and 2-chloro-2-deoxy-septanosides.
abstract: A kinetic study of the hydrolytic stabilities of mono-, di-, and 2-chloro-2-deoxy septanosides, under acid-catalysis, is reported herein. A comparison of mono- and diseptanosides, shows that the glycosidic bond in the disaccharide is more stable than the monosaccharide. Further the glycosidic bond at the reducing end hydrolyzes almost twice as faster than that of the non-reducing end of the disaccharide. 2-Chloro-2-deoxy septanoside is found to be the most stable and its glycosidic bond hydrolysis occurs at elevated temperatures only. The orientation of the exo-cyclic hydroxymethyl group and the inductive effect are suggested to play a role in the rates of hydrolysis.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
authors.forename: Supriya
authors.initials: S
authors.lastname: Dey
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. Electronic address: jayaraman@orgchem.iisc.ernet.in.
authors.forename: N
authors.initials: N
authors.lastname: Jayaraman
mesh_terms: D000143:Acids / Q000737:chemistry; D002236:Carbohydrate Conformation; D002384:Catalysis; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006868:Hydrolysis; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000143:Acids; D004187:Disaccharides; D006027:Glycosides; D009005:Monosaccharides
keywords: Carbohydrates; Glycosidic bond; Hydrolysis; Kinetics; Septanosides