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

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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−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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          Most cited references22

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          Chemical glycobiology.

          Chemical tools have proven indispensable for studies in glycobiology. Synthetic oligosaccharides and glycoconjugates provide materials for correlating structure with function. Synthetic mimics of the complex assemblies found on cell surfaces can modulate cellular interactions and are under development as therapeutic agents. Small molecule inhibitors of carbohydrate biosynthetic and processing enzymes can block the assembly of specific oligosaccharide structures. Inhibitors of carbohydrate recognition and biosynthesis can reveal the biological functions of the carbohydrate epitope and its cognate receptors. Carbohydrate biosynthetic pathways are often amenable to interception with synthetic unnatural substrates. Such metabolic interference can block the expression of oligosaccharides or alter the structures of the sugars presented on cells. Collectively, these chemical approaches are contributing great insight into the myriad biological functions of oligosaccharides.
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            Chiral separation by capillary electromigration techniques.

            This review gives an overview of chiral separation principles and their applications in capillary electromigration techniques. The basic chiral separation principles are explained and the mechanisms discussed. Recent developments and new techniques in CZE and capillary electrochromatography (CEC) are highlighted. New chiral selectors among cyclodextrins, crown ethers, carbohydrates, macrocyclic antibiotics, proteins, chiral ion-pairing reagents, chiral surfactants and chiral metal ion complexes and their chiral recognition ability are discussed. Recent advances in chip technology for chiral separation and new approaches regarding improvement of detection sensitivity are presented. Due to the tremendous number of publications dealing with applications, in this review only recent applications are summarized.
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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                17 January 2011
                January 2011
                : 16
                : 1
                : 652-664
                Affiliations
                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.
                Article
                molecules-16-00652
                10.3390/molecules16010652
                6259221
                21242944
                c2eb9590-a5e6-4fff-b42b-400ae1533c72
                © 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/).

                History
                : 15 December 2010
                : 28 December 2010
                : 13 January 2011
                Categories
                Article

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

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