Analytical Sciences

Abstract − Analytical Sciences, 14(2), 375 (1998).

Chiral Separation of (R,S)-1,1˘­Binaphthyl-2,2˘­diyl Hydrogenphosphate by Capillary Electrophoresis Using Monosaccharides as Chiral Selectors
Hiroshi NAKAMURA * , Akira SANO and Hiroko SUMII Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences, Science University of Tokyo, Ichigaya-funagawara-machi, Shinjuku, Tokyo 162-0826, Japan
Monosaccharides were investigated as chiral selectors in capillary electrophoresis of binaphthyl compounds. Among monosaccharides tested, glucose, mannose and their derivatives, except for methyl- b-D-glucopyranoside, were found to be effective for direct separation of racemic mixture of 1,1˘­binaphthyl-2,2˘­diyl hydrogenphosphate (BNP). D-Forms of galactose, sorbose, fructose, ribose, arabinose and xylose failed chiral separation of BNP. We tentatively concluded that monosaccharides (in the case of D-forms) must satisfy the following structural requirements for successful chiral separa-tion of BNP enantiomers: (1) oxygen atom at C-1 is in a-configuration, (2) -OH group at C-4 is downward configurated and (3) the presence of a -CH2OH or -CH3 group at C-5. Thus, in the case of D-glucose, the chiral separation of BNP is anticipated to be achieved predominantly through the hydrogen bonding between oxygen atom at C-1 and hydrogen atom of -OH group at C-4 on D-glucose and hydrogenphosphate moiety of BNP.