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Food Chemistry
Volume 81, Issue 3, June 2003, Pages 403-409
 
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doi:10.1016/S0308-8146(02)00470-3    How to Cite or Link Using DOI (Opens New Window)
Copyright © 2002 Elsevier Science Ltd. All rights reserved.

Mechanism of imidazole and oxazole formation in [13C-2]-labelled glycine and alanine model systems

Varoujan A. YaylayanCorresponding Author Contact Information, E-mail The Corresponding Author and Luke J. W. Haffenden

McGill University, Department of Food Science and Agricultural Chemistry 21,111 Lakeshore, Ste. Anne de Bellevue, Quebec, Canada, H9X 3V9

Received 27 May 2002; 
revised 8 October 2002; 
accepted 8 October 2002. ;
Available online 17 January 2003.

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Abstract

Studies with 13C-2-labelled glycine and alanine in model systems containing 2,3-butanedione, glyceraldehyde or glyoxal have indicated that imidazoles and oxazoles can be formed from α-dicarbonyl compounds through Strecker reaction and subsequent formation of α-amino carbonyl reactive intermediates. These intermediates can react with any aldehyde in the reaction mixture to form an imine which in turn can either cyclize to form oxazoles or react with an amino compound and then cyclize to form imidazole after an oxidation step. On the other hand, Amadori products, formed in α-hydroxycarbonyl containing systems, can undergo decarboxylation followed by reaction with ammonia to form an amino imine intermediate which, after reaction with any aldehyde followed by cyclization, can form imidazoles after a dehydration step. This latter mechanism fixes the C-2 atom of glycine as an N-alkyl substituent in imidazoles. In addition, model studies with α-dicarbonyl compounds, using ammonium carbonate as a source of ammonia and paraformaldehyde as a source of formaldehyde, also produced imidazoles and oxazoles.

Author Keywords: Amadori product; Maillard reaction; 13C-labelled glycine and alanine; Imidazole; Oxazole formation mechanism; Py-GC/MS

Article Outline

1. Introduction
2. Materials and methods
2.1. Materials
2.2. Pyrolysis GC/MS analysis
3. Results and discussion
Acknowledgements
References







Food Chemistry
Volume 81, Issue 3, June 2003, Pages 403-409
 
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