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.
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.
Röhrling
Jürgen
J
Christian-Doppler-Laboratory, Institute of Chemistry, University of Agricultural Sciences, Muthgasse 18, A-1190 Vienna, Austria.
Potthast
Antje
A
Lange
Thomas
T
Rosenau
Thomas
T
Adorjan
Immanuel
I
Hofinger
Andreas
A
Kosma
Paul
P
D000447:Aldehydes; D002475:Cellobiose; D002482:Cellulose / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D007659:Ketones; D008757:Methylglucosides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D010084:Oxidation-Reduction; D013194:Staining and Labeling
D000447:Aldehydes; D004187:Disaccharides; D005456:Fluorescent Dyes; D007659:Ketones; D008757:Methylglucosides; D002475:Cellobiose; C027020:methylglucoside; D002482:Cellulose