Determination of the side-products formed during the nitroxide-mediated bleach oxidation of glucose to glucaric acid.
The side products formed in the TEMPO-mediated oxidation of glucose to glucaric acid were determined by GC. Next to glucaric acid, gluconic acid, the intermediate in the oxidation, the degradation products, oxalic acid, tartronic acid, meso- (erythraric) and DL-threaric (tartaric) acid were detected. Chiral GC determined the DL-tartaric acid to be non-racemic mixtures of L- and D-tartaric acids, with inverse D/L-ratios depending on the oxidation of D- or L-glucose. The origin of all degradation products is rationalized. This study details a fast screening method to optimize the reaction conditions toward minimal degradation.
Ibert
Mathias
M
UMR 1064-IRCOF-INSA de Rouen, BP08, F-76131 Mont Saint Aignan cedex, France.
Marsais
Francis
F
Merbouh
Nabyl
N
Brückner
Christian
C
D001965:Bromides / Q000737:chemistry; D002849:Chromatography, Gas; D003497:Cyclic N-Oxides / Q000378:metabolism; D005937:Glucaric Acid / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D017670:Sodium Compounds / Q000737:chemistry; D013644:Tartrates / Q000737:chemistry
D001965:Bromides; D003497:Cyclic N-Oxides; D017670:Sodium Compounds; D013644:Tartrates; D005947:Glucose; C027938:sodium bromide; D005937:Glucaric Acid; C003959:TEMPO; C029768:tartaric acid