Glucose phenylosazone

D-Glucosone (XII), prepared from D-glucose phenylosazone (XI) by the action of concentrated hydrochloric acid, is treated in aqueous solution with potassium cyanide. The imino-D-glucoascorbic acid (XIV) which readily separates shows many of the properties of ascorbic acid. Thus it shows a strong selective absorption band in the ultra-... 

The formation of D-glucose phenylosazone from chitosamine showed its relationship to D-glucose and D-mannose and Irvine and Hynd7 succeeded in preparing both D-mannose and D-glucose from chitosamine. 

Although no D-glucosone was obtained by the action of formaldehyde on D-glucose phenylosazone,19 Briill28 successfully decomposed the osazone with an excess of pyruvic acid. An improved procedure has been described, and the decomposition of D-glucose phenylosazone with glyoxal has been reported.18... 

Partially methylated derivatives of D-glucosone have been prepared by decomposition of the corresponding partially methylated phenylosazones with p-nitrobenzaldehyde osones have been obtained from 5-0-methyl-D-glucose phenylosazone and from 3,4,5-tri-O-methyl-D-glucose phenylosazone in this way.22 Although 6-0-methyl-D-glucose phenylosazone is not altered by heating with benzaldehyde or piperonal in aqueous ethanolic... 

It has recently been reported21 that a mixed osazone of 3,4-di-O-methyl-D-glucose can be converted, by treatment with p-nitrobenzaldehyde, into an osone which reacts with phenylhydrazine to give 3,4-di-O-methyl-D-glucose phenylosazone. Von Lebedev29 claimed to have obtained D-glu-cosone 6-phosphate, isolated as an amorphous lead salt, by the action of hydrochloric acid on the phenylosazone prepared from D-fructose 6-phosphate. 

Bayne, Fewster and Mitchell16 prepared VII by the method of Stacey and Turton, and recorded physical properties closely agreeing with those reported by Maurer.66 The compound was clearly related to D-glucosone, prepared from D-glucose phenylosazone and by direct oxidation, since, on treatment with dry acetone containing concentrated sulfuric acid, it gave crystalline tri-0-isopropylidene-(2-hydroxy-D-arabmo-hexose). 7... 

Die Konstitution des Diels schen Anhydro-D-glucose-phenylosazons, by E. Schreier (1953). 

Natural glucosamine gave glucose phenylosazone. D-Arabinose treated with hydrocyanic acid and ammonia formed a nitrile which could be... 

The reaction of glucose with an excess of phenylhydrazine (phenyl-diazane) is particularly noteworthy because two phenylhydrazine molecules are incorporated into one of glucose. Subsequent to the expected phenyl-hydrazone formation, and in a manner that is not entirely clear, the —CHOH— group adjacent to the original aldehyde function is oxidized to a carbonyl group, which then consumes more phenylhydrazine to form a crystalline derivative called an osazone, or specifically glucose phenylosazone ... 

Early investigators98 considered an unestablished sugar designated glutose to be an unfermentable, molasses component and to be iso-lable from this unfermentable residue as its phenylosazone. Later work94 showed that glutose phenylosazone was an impure D-glucose phenylosazone. 

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