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Mechanisms of oxidative degradation of carbohydrates during oxygen delignificaion. III. Reaction of photochemically generated hydroxyl radicals with 1.5-androcellobitol

Authors

Barbara Cole Joe Genco Ray Fort

 

Abstract

Hydroxyl radicals, generated photochemically from hydrogen peroxide in queous base, have been shown to cleave directly glycosidic linkages in methyl β-D-glucoside and methyl β-cellobioside [1,2]. In this paper we show that hydroxyl radicals are responsible for the degradation of glycosidic linkages in 1,5-anhydrocellobitol and 2-methoxytetrahydropyran by substitution reactions displacing 1-deoxyglucose, D-glucose, tetrahydropyran-2- ol and methanol. Once the glycosidic linkages are broken, reducing carbohydrates undergo a series of reactions forming aldonic acids and lower order aldoses in the same manner as described previously [1,2]. Under these same conditions, hydroxyl radicals degrade cellulose substantially as evidenced by viscosity loss.
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NSF EPSCoR The University of Maine EPSCoR Department of Energy
This project is supported by the National Science Foundation under Grant No. EPS-0554545 This project is supported by the Department of Energy EPSCoR program under award number DE-FG02-07ER46373