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Quantitation of 3-aminopropionamide in potatoes-a minor but potent precursor in acrylamide formation.
J Agric Food Chem. 2004 Jul 28; 52(15):4751-7.JA

Abstract

3-Aminopropionamide (3-APA) has recently been suggested as a transient intermediate in acrylamide (AA) formation during thermal degradation of asparagine initiated by reducing carbohydrates or aldehydes, respectively. 3-APA may also be formed in foods by an enzymatic decarboxylation of asparagine. Using a newly developed method to quantify 3-APA based on liquid chromatography/tandem mass spectrometry, it could be shown that the biogenic amine was present in several potato cultivars in different amounts. Further experiments indicated that 3-APA is formed during storage of intact potatoes (20 or 35 degrees C) or after crushing of the cells. The heating of 3-APA under aqueous or low water conditions at temperatures between 100 and 180 degrees C in model systems always generated more AA than in the same reaction of asparagine, thereby pointing to 3-APA as a very effective precursor of AA. While the highest yields measured were about 28 mol % in the presence of carbohydrates (170 degrees C; aqueous buffer), in the absence of carbohydrates, 3-APA was even converted by about 63 mol % into AA upon heating at 170 degrees C under aqueous conditions. Propanoic acid amides bearing an amino or hydroxy group in the alpha-position, such as 2-hydroxypropionamide and l-alaninamide, were ineffective in AA generation indicating that elimination occurs only from the beta-position.

Authors+Show Affiliations

Granvogl M
Lehrstuhl für Lebensmittelchemie, Technische Universität München, Lichtenbergstrasse 4, D-85748 Garching, Germany.
Jezussek M
No affiliation info available
Koehler P
No affiliation info available
Schieberle P
No affiliation info available

MeSH

AcrylamideDecarboxylationGas Chromatography-Mass SpectrometryHot TemperatureSolanum tuberosumWaterbeta-Alanine

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15264910

Citation

Granvogl, Michael, et al. "Quantitation of 3-aminopropionamide in Potatoes-a Minor but Potent Precursor in Acrylamide Formation." Journal of Agricultural and Food Chemistry, vol. 52, no. 15, 2004, pp. 4751-7.
Granvogl M, Jezussek M, Koehler P, et al. Quantitation of 3-aminopropionamide in potatoes-a minor but potent precursor in acrylamide formation. J Agric Food Chem. 2004;52(15):4751-7.
Granvogl, M., Jezussek, M., Koehler, P., & Schieberle, P. (2004). Quantitation of 3-aminopropionamide in potatoes-a minor but potent precursor in acrylamide formation. Journal of Agricultural and Food Chemistry, 52(15), 4751-7.
Granvogl M, et al. Quantitation of 3-aminopropionamide in Potatoes-a Minor but Potent Precursor in Acrylamide Formation. J Agric Food Chem. 2004 Jul 28;52(15):4751-7. PubMed PMID: 15264910.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Quantitation of 3-aminopropionamide in potatoes-a minor but potent precursor in acrylamide formation. AU - Granvogl,Michael, AU - Jezussek,Magnus, AU - Koehler,Peter, AU - Schieberle,Peter, PY - 2004/7/22/pubmed PY - 2004/9/15/medline PY - 2004/7/22/entrez SP - 4751 EP - 7 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 52 IS - 15 N2 - 3-Aminopropionamide (3-APA) has recently been suggested as a transient intermediate in acrylamide (AA) formation during thermal degradation of asparagine initiated by reducing carbohydrates or aldehydes, respectively. 3-APA may also be formed in foods by an enzymatic decarboxylation of asparagine. Using a newly developed method to quantify 3-APA based on liquid chromatography/tandem mass spectrometry, it could be shown that the biogenic amine was present in several potato cultivars in different amounts. Further experiments indicated that 3-APA is formed during storage of intact potatoes (20 or 35 degrees C) or after crushing of the cells. The heating of 3-APA under aqueous or low water conditions at temperatures between 100 and 180 degrees C in model systems always generated more AA than in the same reaction of asparagine, thereby pointing to 3-APA as a very effective precursor of AA. While the highest yields measured were about 28 mol % in the presence of carbohydrates (170 degrees C; aqueous buffer), in the absence of carbohydrates, 3-APA was even converted by about 63 mol % into AA upon heating at 170 degrees C under aqueous conditions. Propanoic acid amides bearing an amino or hydroxy group in the alpha-position, such as 2-hydroxypropionamide and l-alaninamide, were ineffective in AA generation indicating that elimination occurs only from the beta-position. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/15264910/Quantitation_of_3_aminopropionamide_in_potatoes_a_minor_but_potent_precursor_in_acrylamide_formation_ DB - PRIME DP - Unbound Medicine ER -