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Molecules 2011, 16(1), 652-664; doi:10.3390/molecules16010652

Monosaccharide-NAIM Derivatives for D-, L-Configurational Analysis

Genomics Research Center, Academia Sinica, No. 128, Academia Road Section 2, Nankang, Taipei 11529, Taiwan
These authors contributed equally to this work.
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Author to whom correspondence should be addressed.
Received: 15 December 2010 / Revised: 28 December 2010 / Accepted: 13 January 2011 / Published: 17 January 2011
(This article belongs to the Special Issue Glycosides)
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Abstract

The D-, L-enantiomeric pairs of common monosaccharides (xylose, ribose, rhamnose, arabinose, fucose, glucose, mannose, galactose, N-acetylgalactosamine, glucuronic acid and galacturonic acid) were derivatized with 2,3-naphthalenediamine to form the corresponding D-, L-aldo-NAIM derivatives. A simple and facile capillary electrophoretic method was established for sugar composition analysis by simultaneously determining the migration times of these aldo-NAIMs using borate buffer at high pH (100 mM, pH 9.0). The methodology is also applicable to sialic acid (ketose monosaccharides). The quantitation level of the proposed method was in the 10~500 ppm range and the LOD was 1 ppm. The enantioseparation of D, L pairs of aldo-NAIMs were also achieved by using modified sulfated-a-cyclodextrin as the chiral selector in phosphate buffer (300 mM, pH 3.0). In addition, the combination by reductive amination of amino-aldo-NAIM agent and D-, L-enantiomeric pairs of monosaccharides formed a diastereomeric pair for saccharide configuration analysis. Aldo-NAIM derivatives are thus shown to be rapid and efficient agents for analyzing saccharide compositions and configurations with good linearity and short analysis times via capillary electrophoresis.
Keywords: enantioseparation; 2,3-naphthalene diamine; D-; L-monosaccharides; ligand-exchange capillary electrophoresis; cyclodextrin enantioseparation; 2,3-naphthalene diamine; D-; L-monosaccharides; ligand-exchange capillary electrophoresis; cyclodextrin
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

Lin, C.; Kuo, C.-Y.; Liao, K.-S.; Yang, W.-B. Monosaccharide-NAIM Derivatives for D-, L-Configurational Analysis. Molecules 2011, 16, 652-664.

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