Separation of aldose enantiomers by capillary electrophoresis in the presence of optically active N-dodecoxycarbonylvalines

The 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatives of aldose enantiomers were well separated from each other by capillary zone electrophoresis using a neutral phosphate buffer containing an optically active N-dodecoxycarbonylvaline (DCV). The l-enantiomers migrated first and the d-enantiomers foll...

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Bibliographic Details
Published in:	Journal of Chromatography A Vol. 792; no. 1-2; pp. 385 - 391
Main Authors:	Honda, Susumu, Taga, Atsushi, Kotani, Masumi, Grover, Edward R
Format:	Journal Article
Language:	English
Published:	Elsevier B.V 19-12-1997
Subjects:	Aldose Carbohydrates Dodecoxycarbonylvaline Phenylmethylpyrazolone Carbohydrates Aldose Phenylmethylpyrazolone Dodecoxycarbonylvaline Enantiomer separation
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Summary:	The 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatives of aldose enantiomers were well separated from each other by capillary zone electrophoresis using a neutral phosphate buffer containing an optically active N-dodecoxycarbonylvaline (DCV). The l-enantiomers migrated first and the d-enantiomers followed, when R-DCV was added to electrophoretic solution, and the migration order was reversed for the addition of S-DCV. This separation was inherent to PMP derivatives; other derivatives such as 2-aminopyridine, 8-aminonaphthalene-1,3,6-trisulfonate and 4-nitrobenz-2-oxa-1,3-diazole-tagged glycamine derivatives were not separated at all. l-Lauroylvaline and sodium dodecyl sulfate were also not separated. Based on these results, together with the 1H NMR signal change (upfield shift of the carbohydrate-proton signals in PMP–aldoses) on addition of R-DCV, we speculated this separation to be due to the difference in the ease of intermolecular ring formation by hydrogen bonding.
ISSN:	0021-9673
DOI:	10.1016/S0021-9673(97)00926-6