Cart
Article
Why Asparagine Needs Carbohydrates To Generate Acrylamide
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Section:Abstract
Structural considerations dictate that asparagine alone may be converted thermally into acrylamide through decarboxylation and deamination reactions. However, the main product of the thermal decomposition of asparagine was maleimide, mainly due to the fast intramolecular cyclization reaction that prevents the formation of acrylamide. On the other hand, asparagine, in the presence of reducing sugars, was able to generate acrylamide in addition to maleimide. Model reactions were performed using FTIR analysis, and labeling studies were carried out using pyrolysis-GC/MS as an integrated reaction, separation, and identification system to investigate the role of reducing sugars. The data have indicated that a decarboxylated Amadori product of asparagine with reducing sugars is the key precursor of acrylamide. Furthermore, the decarboxylated Amadori product can be formed under mild conditions through the intramolecular cyclization of the initial Schiff base and formation of oxazolidin-5-one. The low-energy decarboxylation of this intermediate makes it possible to bypass the cyclization reaction, which is in competition with thermally induced decarboxylation, and hence promote the formation of acrylamide in carbohydrate/asparagine mixtures. Although the decarboxylated Amadori compound can be formed under mild conditions, it requires elevated temperatures to cleave the carbon−nitrogen covalent bond and produce acrylamide.
Keywords: Asparagine; acrylamide; mechanism; decarboxylated Amadori product; FTIR; Py-GC/MS; 13C-labeled glucose
Citing Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 47 ACS Journal articles (5 most recent appear below).
Influence of precursor content, varietal selection, roasting time and temperature, and storage temperature on acrylamide formation in almonds (Prunus dulcis)
Gong Zhang , Guangwei Huang , Lu Xiao , James N. Seiber , and Alyson Elayne MitchellJournal of Agricultural and Food Chemistry 0 (ja),Influence of precursor content, varietal selection, roasting time and temperature, and storage temperature on acrylamide formation in almonds (Prunus dulcis)
Gong Zhang , Guangwei Huang , Lu Xiao , James N. Seiber , and Alyson Elayne MitchellJournal of Agricultural and Food Chemistry 0 (ja),Acrylamide is a probable human carcinogen that is found in many roasted and baked foods. Although safety standards have not been adopted for levels in foods, levels below 200 ppb are targeted. Herein we describe two sensitive and reliable LC-(ESI)MS/MS ...
Ultra High-Performance Liquid Chromatography−Tandem Mass Spectrometry for the Simultaneous Analysis of Asparagine, Sugars, and Acrylamide in Maillard Reactions
Yu Zhang, Yiping Ren, Jingjing Jiao, Dong Li, and Ying ZhangAnalytical Chemistry2011 Article ASAPUltra High-Performance Liquid Chromatography−Tandem Mass Spectrometry for the Simultaneous Analysis of Asparagine, Sugars, and Acrylamide in Maillard Reactions
Yu Zhang, Yiping Ren, Jingjing Jiao, Dong Li, and Ying ZhangAnalytical Chemistry2011 Article ASAPWe developed an automated microwave digestion labstation (MDL) combined with ultra high-performance liquid chromatography−tandem mass spectrometry (UHPLC−MS/MS) method under the control of positive−negative ion switching as a robust kinetic study tool for ...
Dimerization of Azomethine Ylides: An Alternate Route to Pyrazine Formation in the Maillard Reaction
Paula Vanessa Guerra and Varoujan A. YaylayanJournal of Agricultural and Food Chemistry2010 58 (23), 12523-12529Dimerization of Azomethine Ylides: An Alternate Route to Pyrazine Formation in the Maillard Reaction
Paula Vanessa Guerra and Varoujan A. YaylayanJournal of Agricultural and Food Chemistry2010 58 (23), 12523-12529Recently, azomethine ylides have been implicated as reactive intermediates in the Maillard reaction. They are known to undergo 1,3-cycloaddition reactions with dipolarophiles to form pyrroles, and, more importantly, they can undergo dimerization reaction ...
Asparagine Decarboxylation by Lipid Oxidation Products in Model Systems
Francisco J. Hidalgo, Rosa M. Delgado, José L. Navarro, and Rosario ZamoraJournal of Agricultural and Food Chemistry2010 58 (19), 10512-10517Asparagine Decarboxylation by Lipid Oxidation Products in Model Systems
Francisco J. Hidalgo, Rosa M. Delgado, José L. Navarro, and Rosario ZamoraJournal of Agricultural and Food Chemistry2010 58 (19), 10512-10517The decarboxylation of asparagine in the presence of alkanals, alkenals, and alkadienals, among other lipid derivatives, was studied in an attempt to understand the reaction pathways by which some lipid oxidation products are able to convert asparagine ...
Model Reactions of Acrylamide with Selected Amino Compounds
Rosario Zamora, Rosa M. Delgado and Francisco J. HidalgoJournal of Agricultural and Food Chemistry2010 58 (3), 1708-1713Model Reactions of Acrylamide with Selected Amino Compounds
Rosario Zamora, Rosa M. Delgado and Francisco J. HidalgoJournal of Agricultural and Food Chemistry2010 58 (3), 1708-1713The reaction of acrylamide with amines, amino acids, and polypeptides was studied in an attempt to understand the role of amino compounds on acrylamide fate. The obtained results showed that amino compounds are added to acrylamide by means of a Michael ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue March 12, 2003
- Received for review November 21, 2002. Revised manuscript received January 7, 2003. Accepted January 13, 2003. We acknowledge funding for this research by the Natural Sciences and Engineering Research Council of Canada (NSERC).
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
chiefly in commercially available potato chips, potato fries, cereals, and bread
