New aspects on the formation and analysis of acrylamide.
The effectiveness of different compounds in the generation of acrylamide (AA) from asparagine, was determined by reacting asparagine with mono-, di- and polysaccharides, as well as four different oxo-compounds known to be involved in carbohydrate metabolism/degradation. Quantitation of AA formed either under aqueous conditions or in low water model systems revealed glucose and 2-oxopropionic acid as the most effective compounds in AA generation, when reacted in model systems with a low water content (about 1 mol-% yield). Interestingly, heating of asparagine in the presence of 2-oxopropionic acid generated quite high amounts of 3-aminopropionamide (3-APA), which itself effectively generated AA upon heating in aqueous solution, as well as in low water systems. Because this is the first report on amounts of 3-APA generated by Maillard-type reactions, the general role of 3-APA as key intermediate in AA formation is discussed in detail. In addition, first results on the development and application of an HPLC/fluorescence method for AA quantitation are presented.
Schieberle
Peter
P
Lehrstuhl für Lebensmittelchemie der Technischen Universität München, Lichtenbergstrasse 4, D-85748 Garching, Germany. Peter.Schieberle@Lrz.tum.de
Köhler
Peter
P
Granvog
Michael
M
D020106:Acrylamide / Q000737:chemistry*; D000409:Alanine / Q000031:analogs & derivatives / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D001216:Asparagine / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005504:Food Analysis; D005947:Glucose / Q000737:chemistry; D015416:Maillard Reaction; D013058:Mass Spectrometry; D008956:Models, Chemical; D011134:Polysaccharides / Q000737:chemistry; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013696:Temperature; D013997:Time Factors; D014867:Water / Q000737:chemistry
C094933:2-amino-3-oxopropionic acid; D000447:Aldehydes; D000577:Amides; D002241:Carbohydrates; D011134:Polysaccharides; D014867:Water; D020106:Acrylamide; D058428:Silica Gel; D001216:Asparagine; D012822:Silicon Dioxide; D005947:Glucose; D000409:Alanine; C034666:propionamide