Synthesis of oxidized methyl 4-O-methyl-beta-D-glucopyranoside and methyl beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside derivatives as substrates for fluorescence labeling reactions |
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Authors: | Röhrling Jürgen Potthast Antje Lange Thomas Rosenau Thomas Adorjan Immanuel Hofinger Andreas Kosma Paul |
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Institution: | Christian-Doppler-Laboratory, Institute of Chemistry, University of Agricultural Sciences, Muthgasse 18, A-1190 Vienna, Austria. |
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Abstract: | The synthetic cellulose model compounds methyl 4-O-methyl-beta-D-glucopyranoside and methyl 4-O-methyl-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranoside and related 6-O-protected intermediates were oxidized in good to fair yields using Swern-conditions or bromine/bis(tributyltin) oxide, respectively, to afford compounds containing 6-aldehyde, 3-keto, and 2,3-diketo groups. Cellobiose and oxidized monosaccharides were then labeled with the carbonyl-selective fluorescence marker 9-(7-amino-1,4,7-trioxaheptyl)-9H-carbazolecarboxamide (CCOA). The labeled derivatives serve as model compounds for the determination of minute amounts of carbonyl groups in cellulosic polysaccharides. |
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Keywords: | Oxidation Cellulose Cellobioside Fluorescence labelling |
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