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

Roquette Frères Society, Lestrem cedex, France.

Carbohydrate research 2011 Mar 1

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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.

Citation

Mathias Ibert, Patrick Fuertès, Nabyl Merbouh, Christian Feasson, Francis Marsais. Evidence of benzilic rearrangement during the electrochemical oxidation of D-glucose to D-glucaric acid. Carbohydrate research. 2011 Mar 1;346(4):512-8