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Molecules 2011, 16(2), 1682-1694; doi:10.3390/molecules16021682

Bis-Indole Derivatives for Polysaccharide Compositional Analysis and Chiral Resolution of D-, L-Monosaccharides by Ligand Exchange Capillary Electrophoresis Using Borate-Cyclodextrin as a Chiral Selector

Genomics Research Center, Academia Sinica, No. 128, Academia Road Section 2, Nankang, Taipei 11529, Taiwan
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 22 December 2010 / Accepted: 16 February 2011 / Published: 17 February 2011
(This article belongs to the Special Issue Glycosides)
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Abstract

A series of aldo-bis-indole derivatives (aldo-BINs) was prepared by aromatic C-alkylation reactions of aldoses and indole in acetic acid solution. Common monosaccharides such as glucose, mannose, galactose, fucose, xylose, rhamnose, ribose, arabinose and N-acetylglucosamine were smoothly derivatized to form the UV absorbing aldo-BINs. The use of a capillary electrophoretic method to separate these novel aldo-BIN derivatives was established. The capillary electrophoresis conditions were set by using borate buffer (100 mM) at high pH (pH 9.0). The limit of determination was assessed to be 25 nM. The enantioseparation of D, L-pairs of aldo-BINs based on chiral ligand-exchange capillary electrophoresis technology was also achieved by using modified hydroxypropyl-β-cyclodextrin as the chiral selector in the presence of borate buffer. This aldose labeling method was applied successfully to the compositional and configurational analysis of saccharides, exemplified by a rapid and efficient method to simultaneously analyze the composition and configuration of saccharides from the medicinal herbs Cordyceps sinensis and Dendrobium huoshanense.
Keywords: monosaccharides; indole; enantioseparation; cyclodextrin; ligand-exchange capillary electrophoresis (LECE) monosaccharides; indole; enantioseparation; cyclodextrin; ligand-exchange capillary electrophoresis (LECE)
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Kuo, C.-Y.; Liao, K.-S.; Liu, Y.-C.; Yang, W.-B. Bis-Indole Derivatives for Polysaccharide Compositional Analysis and Chiral Resolution of D-, L-Monosaccharides by Ligand Exchange Capillary Electrophoresis Using Borate-Cyclodextrin as a Chiral Selector. Molecules 2011, 16, 1682-1694.

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