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


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          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−α−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.

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                Author and article information

                17 January 2011
                January 2011
                : 16
                : 1
                : 652-664
                Genomics Research Center, Academia Sinica, No. 128, Academia Road Section 2, Nankang, Taipei 11529, Taiwan
                Author notes

                These authors contributed equally to this work.

                [* ] Author to whom correspondence should be addressed; Email: wbyang@ 123456gate.sinica.edu.tw ; Tel.: +886-2-27871264; Fax: +886-2-27871264.
                © 2011 by the authors;

                licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                : 15 December 2010
                : 28 December 2010
                : 13 January 2011

                enantioseparation,2,3-naphthalene diamine,d-, l-monosaccharides,ligand-exchange capillary electrophoresis,cyclodextrin


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