Carbohydrate Research 2011-03-01

Evidence of benzilic rearrangement during the electrochemical oxidation of D-glucose to D-glucaric acid.

Mathias Ibert, Patrick Fuertès, Nabyl Merbouh, Christian Feasson, Francis Marsais

Index: Carbohydr. Res. 346(4) , 512-8, (2011)

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Abstract

During the course of the 2,2,6,6-tetramethyl-1-piperidinyloxy free radical-catalyzed electrochemical oxidation of D-glucose to D-glucaric acid a new side-product was observed. This compound was isolated and identified as a tricarboxylic acid of unique structure, which was named maribersonic acid. Its structure was proven by different experiments coupled with several analytical methods, and its appearance during the electrochemical oxidation of D-glucose was rationalized through a thorough study.Copyright © 2010 Elsevier Ltd. All rights reserved.