2-C-CARBOXYALDOSES AND ALDONIC ACIDS FROM CELLOBIOSE, MALTOSE, AND 4-O-METHYL-D-GLUCOSE WITH 2-ANTHRAQUINONESULFONIC ACID

Article abstract of DOI:10.1016/S0008-6215(00)90462-2

Cellobiose, maltose, and 4-O-methyl-D-glucose were treated with 0.1-20mM 2-anthraquinonsulfonic acid in 0.1M sodium hydroxide at 40 deg C.The hydroxy carboxylic acids formed were separated by ion-exchange, and analyzed by g.l.c.-m.s. as their per(trimethylsilyl) derivatives.The acidic oxidation products of cellobiose were further fractionated into aldonic acids and carboxyaldoses by ion-exchange chromatography.The isolated carboxyaldoses were reduced with sodium borohydride, and then analyzed by g.l.c.-m.s. before and after hydrolysis.The O-D-glucosyl- and O-methyl-substituted products of the sugars consisted of erythronic, arabinonic, ribonic, gluconic, and mannonic acids, in addition to 2-C-carboxypentoses.The nonsubstituted products of the reducing D-glucose unit were formic, glycolic, 2-deoxytetronic, and 3-deoxypentonic acids, and 2-C-carboxy-3-deoxypentoses.