Ability of non-cyclic oligosaccharides to form molecular complexes and its use for chiral separation by capillary zone electrophoresis.
The binding constants (K) for complexation of the phenyl acetates with linear alpha-1,4-linked dextrins have been determined from the kinetics of the hydrolyses of the esters. The K value tends to increase with increasing the number of the glucopyranose units, suggesting hydrophobic interaction as a binding force. The weak ability of the linear dextrins to form the molecular complexes makes it possible to separate the enantiomers of binaphthyl derivatives such as 1,1'-binaphthyl-2,2'-dicarboxylic acid, 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate and 2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarboxylic acid in their anionic forms. Hydrogen bonding as well as hydrophobic interaction is suggested as an essential force for enantioselective complexation between saccharide and anionic binaphthyl.
Kano
K
K
Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyoto, Japan.
Minami
K
K
Horiguchi
K
K
Ishimura
T
T
Kodera
M
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004586:Electrophoresis / Q000379:methods*; D004952:Esters; D006860:Hydrogen Bonding; D006868:Hydrolysis; D008969:Molecular Sequence Data; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification; D009844:Oligosaccharides / Q000737:chemistry*; D013057:Spectrum Analysis; D013237:Stereoisomerism
D004952:Esters; D009281:Naphthalenes; D009844:Oligosaccharides