title: Reaction of folic acid with reducing sugars and sugar degradation products.
abstract: 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%).
authors.affiliation: Institut für Pharmazie und Lebensmittelchemie der Universität Erlangen-Nürnberg, D-91052 Erlangen, Germany.
authors.forename: Marc
authors.initials: M
authors.lastname: Schneider
authors.forename: Marcus
authors.initials: M
authors.lastname: Klotzsche
authors.forename: Christoph
authors.initials: C
authors.lastname: Werzinger
authors.forename: Jörg
authors.initials: J
authors.lastname: Hegele
authors.forename: Reiner
authors.initials: R
authors.lastname: Waibel
authors.forename: Monika
authors.initials: M
authors.lastname: Pischetsrieder
mesh_terms: 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
chemical_list: D002241:Carbohydrates; D004187:Disaccharides; D009005:Monosaccharides; C452224:N2-(1-(carboxyethyl))folic acid; D005492:Folic Acid; D004098:Dihydroxyacetone