D-Maltobionic acid

Oxidation by bromine water converts (+)-maltose into ihe monocarboxylic acid D-maltobionic acid. Treatment of this acid with methyl sulfate and sodium hydroxide yields (octa-O-methyl-D-maltobionic acid. Upon hydrolysis in acidic solution, the methylated acid yields two products, 2,3,5,6-tetra-O-methyl-o-gluconic acid and 2,3,4,6-tetra-O-methyl-D-glucose. 

Another method of preparing keto aldonic acids, those of the 2-keto type, is by oxidation of the corresponding osone. Neuberg and Kitasato obtained 18 g. of calcium 2-keto-D-gluconate from 20 g. of the osone by the action of bromine at 20 . Similarly, 2-keto-n-galactonic and 2-keto-maltobionic acids were prepared by Kitasato. The substances were characterized generally as the brucine salts because of the amorphous nature of the calcium salts. 

In 1931, Isbell and Frush reported the electrolytic oxidation of aldoses in the presence of calcium carbonate and a small amount of bromide, which served as a catalyst. The main solutes in the reaction mixture are the aldose and the calcium salt of the aldonic acid. The latter is easily crystallized from solution. The salts of D-gluconic, D-xylonic, lactobionic and maltobionic acids were prepared. A description of the process was published in 1932 and a patent was issued in 1934. German and French patents were issued in 1931 to the Rohm and Haas Co. ... 

Fig. 2.—Curves of Rate against Temperature. (A, maltose B, maltitol C, maltose phenylosotriazole D, maltose cyanohydrin E, maltobionic acid F, maltose 1-phenyl-flavazole.)...

Calcium D-galactonate, I, 70 Calcium D-gluconate, III, 141, 142, 149, 152, 155, 156, 161 IV, 331 Calcium hypochlorite, III, 165 Calcium 2-keto-D-gIuconate, III, 148, 155 Calcium 5-keto-D-gluconate, III, 156 Calcium lactobionate, calcium bromide double salt, III, 155 Calcium Ievulinate, IV, 311 Calcium maltobionate, III, 161 Calcium D-mannonate, III, 152 Calcium pectate, I, 334 Calcium D-rhamnonate, III, 144 Calcium salts, in preparation of aldonic acids with NaCN, I, 23 Calcium vicianobionate, III, 154 Calcium D-xylonate, III, 155 Camphor, optically active, formed from inactive (racemic) camphor carboxylic acid in the presence of quinine, quinidine or nicotine, V, 53 Camphor carboxylic acid. See Camphor. Camphor, 3-hydroxy-, IV, 89 Camphorquinone, phytochemical reduction of, IV, 89... 

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