Reaction of folic acid with reducing sugars and sugar degradation products.
The reaction of folic acid with reducing sugars (nonenzymatic glycation) under conditions that can occur during food processing and preparation was studied by high-performance liquid chromatography with diode array detection. N-(p-Aminobenzoyl)-L-glutamic acid, a well-established oxidation product, was detected in the reaction mixtures. Furthermore, a new product was isolated and identified as N2-[1-(carboxyethyl)]folic acid (CEF). CEF was the main product that was formed by the nonenzymatic glycation of folic acid. For preparation, N2-[1-(carboxyethyl)]folic acid was obtained in high yields when folic acid and dihydroxyacetone (DHA), a sugar degradation product, were heated at 100 degrees C in phosphate buffer. Mixtures of folic acid and different sugars or DHA were heated under variation of reaction time and temperature, and CEF was quantified. Up to 50% of the vitamin was converted to CEF, with highest yields formed from maltose (49%) and lactose (43%).
Schneider
Marc
M
Institut für Pharmazie und Lebensmittelchemie der Universität Erlangen-Nürnberg, D-91052 Erlangen, Germany.
Klotzsche
Marcus
M
Werzinger
Christoph
C
Hegele
Jörg
J
Waibel
Reiner
R
Pischetsrieder
Monika
M
D002241:Carbohydrates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004098:Dihydroxyacetone / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry; D004347:Drug Interactions; D005492:Folic Acid / Q000031:analogs & derivatives / Q000737:chemistry*; D005511:Food Handling; D006358:Hot Temperature; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015416:Maillard Reaction; D009005:Monosaccharides / Q000737:chemistry; D010084:Oxidation-Reduction
D002241:Carbohydrates; D004187:Disaccharides; D009005:Monosaccharides; C452224:N2-(1-(carboxyethyl))folic acid; D005492:Folic Acid; D004098:Dihydroxyacetone