Related Experiment Video
Updated: Jul 17, 2026

Expression, Purification, Crystallization, and Enzyme Assays of Fumarylacetoacetate Hydrolase Domain-Containing Proteins
Published on: June 20, 2019
The Hofer-Moest decarboxylation of D-glucuronic acid and D-glucuronosides
Jonathan A Stapley1, James N Bemiller
1Whistler Center for Carbohydrate Research, Purdue University, 745 Agriculture Mall Drive, West Lafayette, IN 47906-2009, USA.
Abstract:
Research was undertaken to effect the oxidative decarboxylation of glycuronosides. Experiments with free D-glucuronic acid and aldonic acids were also executed. Both anodic decarboxylation and variants of the Ruff degradation reaction were investigated. Anodic decarboxylation was found to be the only successful method for the decarboxylation of glucuronosides. It was, therefore, proposed that glycuronosides can only undergo a one-electron oxidation to form an acyloxy radical, which decomposes to form carbon dioxide and a C-5 radical, that is, a Hofer-Moest decarboxylation. The radical is subsequently oxidized to a cation by means of a second one-electron oxidation. The cation undergoes nucleophilic attack from the solvent (water), whose product (a hemiacetal) undergoes a spontaneous hydrolysis to yield a dialdose (xylo-pentodialdose from D-glucuronosides).
More Related Videos
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
11:08Chemo-enzymatic Synthesis of N-glycans for Array Development and HIV Antibody Profiling
Published on: February 5, 2018
Related Concept Videos
Phase II Reactions: Glucuronidation
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives
Drug Metabolism: Phase II Reactions
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Protein Folding Quality Check in the RER