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

Carbohydr Res. 2011 Mar 1;346(4):512-8. doi: 10.1016/j.carres.2010.12.017. Epub 2010 Dec 30.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glucaric Acid / chemistry*
  • Glucose / chemistry*
  • Oxidation-Reduction
  • Phenylglyoxal / analogs & derivatives
  • Phenylglyoxal / chemistry
  • Piperidines / chemistry
  • Sugar Acids / chemical synthesis*
  • Tricarboxylic Acids / chemical synthesis*

Substances

  • 2,2,6,6-tetramethyl-1-piperidine
  • Piperidines
  • Sugar Acids
  • Tricarboxylic Acids
  • Glucose
  • Phenylglyoxal
  • Glucaric Acid
  • benzil