Degradation of the Amadori compound N-(1-deoxy-D-fructos-1-yl)glycine in aqueous model systems. 2002

Tomas Davidek, and Nathalie Clety, and Sandra Aubin, and Imre Blank
Centres R&D Nestlé SAS, Amiens, P.O. Box 47, 80800 Aubigny, France.

The fate of the Amadori compound N-(1-deoxy-D-fructos-1-yl)glycine (DFG) was studied in aqueous model systems as a function of time and pH. The samples were reacted at 90 degrees C for up to 7 h while maintaining the pH constant at 5, 6, 7, or 8. Special attention was paid to the effect of phosphate on the formation of glycine and the parent sugars glucose and mannose, as well as formic and acetic acid. These compounds and DFG were quantified by high-performance anion-exchange chromatography. The rate of DFG degradation increased with pH. Addition of phosphate accelerated this reaction, particularly at pH 5-7. The rate of glycine formation increased with pH in both the absence and presence of phosphate. High glycine concentrations (60-70 mol %) were obtained, preferably at pH 6-8 with phosphate. However, the yield of glycine formed from DFG decreased at the advanced reaction stage for all pH values studied, both in water and in phosphate buffer. The rate of parent sugar formation increased from pH 5 to pH 7 in the absence of phosphate, leading to glucose and mannose in a constant ratio of 7:3. Addition of phosphate accelerated this reaction, yielding up to 18% parent sugars, most likely formed by reverse Amadori rearrangement. The formation rate of acetic and formic acid increased with increasing pH. The sum of both acids attained 76 mol %. However, the acetic acid concentrations were much higher than those of formic acid.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008358 Mannose A hexose or fermentable monosaccharide and isomer of glucose from manna, the ash Fraxinus ornus and related plants. (From Grant & Hackh's Chemical Dictionary, 5th ed & Random House Unabridged Dictionary, 2d ed) D-Mannose,Mannopyranose,Mannopyranoside,D Mannose
D010710 Phosphates Inorganic salts of phosphoric acid. Inorganic Phosphate,Phosphates, Inorganic,Inorganic Phosphates,Orthophosphate,Phosphate,Phosphate, Inorganic
D002021 Buffers A chemical system that functions to control the levels of specific ions in solution. When the level of hydrogen ion in solution is controlled the system is called a pH buffer. Buffer
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D005561 Formates Derivatives of formic acids. Included under this heading are a broad variety of acid forms, salts, esters, and amides that are formed with a single carbon carboxy group. Formic Acids,Acids, Formic
D005947 Glucose A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. Dextrose,Anhydrous Dextrose,D-Glucose,Glucose Monohydrate,Glucose, (DL)-Isomer,Glucose, (alpha-D)-Isomer,Glucose, (beta-D)-Isomer,D Glucose,Dextrose, Anhydrous,Monohydrate, Glucose
D005998 Glycine A non-essential amino acid. It is found primarily in gelatin and silk fibroin and used therapeutically as a nutrient. It is also a fast inhibitory neurotransmitter. Aminoacetic Acid,Glycine, Monopotassium Salt,Glycine Carbonate (1:1), Monosodium Salt,Glycine Carbonate (2:1), Monolithium Salt,Glycine Carbonate (2:1), Monopotassium Salt,Glycine Carbonate (2:1), Monosodium Salt,Glycine Hydrochloride,Glycine Hydrochloride (2:1),Glycine Phosphate,Glycine Phosphate (1:1),Glycine Sulfate (3:1),Glycine, Calcium Salt,Glycine, Calcium Salt (2:1),Glycine, Cobalt Salt,Glycine, Copper Salt,Glycine, Monoammonium Salt,Glycine, Monosodium Salt,Glycine, Sodium Hydrogen Carbonate,Acid, Aminoacetic,Calcium Salt Glycine,Cobalt Salt Glycine,Copper Salt Glycine,Hydrochloride, Glycine,Monoammonium Salt Glycine,Monopotassium Salt Glycine,Monosodium Salt Glycine,Phosphate, Glycine,Salt Glycine, Monoammonium,Salt Glycine, Monopotassium,Salt Glycine, Monosodium
D006863 Hydrogen-Ion Concentration The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D013997 Time Factors Elements of limited time intervals, contributing to particular results or situations. Time Series,Factor, Time,Time Factor

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