Hiroshi Nakamura, A. Sano, Hiroko Sumii
Apr 1, 1998
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0
Influential Citations
23
Citations
Journal
Analytical Sciences
Abstract
Monosaccharides were investigated as chiral selectors in capillary electrophoresis of binaphthyl compounds. Among monosaccharides tested, glucose, mannose and their derivatives, except for methyl- β - 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 separation of BNP enantiomers: (1) oxygen atom at C-1 is in α-configuration, (2) -OH group at C-4 is downward configurated and (3) the presence of a -CH^2OH or -CH^3 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.