Sugar oxidation reaction

Kline and Acree studied the hypoiodite oxidation extensively. The alkali and iodine were both added in small portions throughout the reaction. In this manner the concentration of sugar relative to the sodium hypoiodite was kept at a level favorable to the sugar oxidation (reaction 14). At the end of the reaction, the formation of iodate increased rapidly (reaction 15), taking precedence over the oxidation of ketoses and non-reducing sugars. 

Other possible chemical synthesis routes for lactic acid include base-cataly2ed degradation of sugars oxidation of propylene glycol reaction of acetaldehyde, carbon monoxide, and water at elevated temperatures and pressures hydrolysis of chloropropionic acid (prepared by chlorination of propionic acid) nitric acid oxidation of propylene etc. None of these routes has led to a technically and economically viable process (6). 

Sugars are easily oxidized. One oxidation reaction that shows this involves cupric hydroxide, O /... 

Phillips (P2) has studied the radiation reactions of sugars in dilute solution and reported a preferential oxidation occurring at the C 6 position, which results in conversion of the glucose to glucuronic acid. Other oxidizing reactions resulting in the formation of aldehyde offer alternative pathways. 

Rates of Enolization Reactions. For a better understanding of the transformation and oxidation reactions of reducing sugars, methods have been developed to measure the primary rates of enolization (18). One of these methods depends on the rate at which tritium ions are released from aldoses-2- to the solvent. This is measured by separation of the water-, sublimation, and radiochemical assay of the water as the reaction proceeds. The rate constant is calculated from the first-order equation ... 

The use of certain vanadium compounds as catalysts has been increasing. Vanadium oxy trichloride is a catalyst in making ediylene-propylene rubber. Ammonium metavanadate and vanadium pentoxide aie used as oxidation catalysts, particularly in the production of polyamides, such as nylon, in the manufacture of H>S04 by the contact process, in the production of phdialic and maleic anhydrides, and in numerous other oxidation reactions, such as alcohol to acetaldehyde, anthracene to anthraquinone, sugar to oxalic acid, and diphenylamine to carbazole. Vanadium compounds have been used for many years 111 die ceramics field for enamels and glazes. Colors are produced by various combinations of vanadium oxide and silica, zirconia, zinc, lead, tin, selenium, and cadmium. Vanadium intermediate compounds also are used in the making of aniline Mack used by the dye industry... 

For the release of an unaltered base, the sugar moiety must be damaged. In principle, the base could already be released from a radical site at the sugar moiety, i.e. on the time-scale of the lifetime of the DNA radicals. The observation of 2-dRL incorporated into DNA as a product formed upon OH attack shows that a damage at C(l ) contributes to the release of an unaltered base. In the carbohydrate series, hydrolytic scission at the glycosidic linkage when this site contains a free-radical is a well-documented phenomenon, and it has been estimated that the rate of reaction must be faster than 35 s 1 (von Sonntag and Schuchmann 2001). As it stands, it cannot be excluded, that under certain conditions the base release from the C(l ) radical [reaction (38)] occurs in competition to its oxidation [reaction (2)]. In a cellular environment, there is also the reduction of DNA... 

H. S. Isbell, Enolization and oxidation reactions of reducing sugars, in R. F. Gould (Ed.), Carbohydrates in solution, Advances in Chemistry, ACS, Washington, 117 (1973) 70-87. 

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