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Thesis Title Elucidation of selected Maillard reaction pathways in alanine and phenylalanine model systems through isotope labelling and pyrolysis-GC/MS based techniques FONG LAM CHU Department of Food Science and Agricultural Chemistry McGill University, Montreal August 2009 Thesis submitted to the Faculty of Graduate and Post-Doctoral studies in partial fulfillment of the requirement of the degree of Doctor in Philosophy © Fong Lam Chu, 2009 Library and Archives Bibliothèque et Canada Archives Canada Published Heritage Direction du Branch Patrimoine de l’édition 395 Wellington Street 395, rue Wellington Ottawa ON K1A 0N4 Ottawa ON K1A 0N4 Canada Canada Your file Votre référence ISBN:978-0-494-61905-6 Our file Notre référence ISBN: 978-0-494-61905-6 NOTICE: AVIS: The author has granted a non- L’auteur a accordé une licence non exclusive exclusive license allowing Library and permettant à la Bibliothèque et Archives Archives Canada to reproduce, Canada de reproduire, publier, archiver, publish, archive, preserve, conserve, sauvegarder, conserver, transmettre au public communicate to the public by par télécommunication ou par l’Internet, prêter, telecommunication or on the Internet, distribuer et vendre des thèses partout dans le loan, distribute and sell theses monde, à des fins commerciales ou autres, sur worldwide, for commercial or non- support microforme, papier, électronique et/ou commercial purposes, in microform, autres formats. paper, electronic and/or any other formats. The author retains copyright L’auteur conserve la propriété du droit d’auteur ownership and moral rights in this et des droits moraux qui protège cette thèse. Ni thesis. Neither the thesis nor la thèse ni des extraits substantiels de celle-ci substantial extracts from it may be ne doivent être imprimés ou autrement printed or otherwise reproduced reproduits sans son autorisation. without the author’s permission. In compliance with the Canadian Conformément à la loi canadienne sur la Privacy Act some supporting forms protection de la vie privée, quelques may have been removed from this formulaires secondaires ont été enlevés de thesis. cette thèse. While these forms may be included Bien que ces formulaires aient inclus dans in the document page count, their la pagination, il n’y aura aucun contenu removal does not represent any loss manquant. of content from the thesis. Suggested Short Title: Elucidation of selected Maillard reaction pathways II Abstract Alanine and phenylalanine based model systems were utilized in this thesis to elucidate selected Maillard reaction pathways through isotope labelling, Fourier Transform Infrared Spectroscopy (FTIR) and Pyrolysis-Gas Chromatography/Mass Spectrometry (Py-GC/MS) based techniques. The formation of glycosylamines from reducing sugars and amino acids is a well-known process in the initial phase of the Maillard reaction. They play a critical role in both the initiation and propagation stages, however, little attention has been paid so far on the ability of these imines to undergo isomerization and thus contribute to the diversity of Maillard reaction products. In this study, imine isomerization through 5-oxazolidinone formation was explored in phenylalanine and alanine sugar models systems. Spectroscopic evidence was provided for its formation by taking advantage of the strong carbonyl absorption band centered at 1784 cm-1 in the phenylalanine/glyceraldehyde and at 1778 cm-1 in phenylalanine/glycolaldehyde model system. The importance of 5-oxazolidinone formation lies in its ability to decarboxylate to azomethine ylide and subsequently form two isomeric imines, each capable of producing distinct Maillard reaction products. Evidence for the formation of such ylides was also provided through their ability to undergo 1,3-dipolar cycloaddition with dipolarophiles. Regarding the role of oxygen in the Maillard reaction, it was found that molecular oxygen can influence carbon-carbon bond cleavage through the formation and degradation of 1,2-dioxetane moieties generated from enol structures abundantly formed in the Maillard reaction from their corresponding ketones and aldehydes such as phenylacetaldehyde the Strecker aldehyde of phenylalanine and subsequently can be oxidized into benzaldehyde. Furthermore, the α-dicarbonyl compounds generated during III the Maillard reaction play a significant role as precursors of important flavour-active heterocyclic compounds. The origin of many such α-dicarbonyl compounds still remains unknown. Using glucose and glyoxal with labelled [13C]- and [15N]-alanine, the mechanism of formation of 1,2-butanedione and 3,4-hexanedione were confirmed and proposed to proceed through amino acid-assisted chain elongation pathway. In addition, the role of α-dicarbonyl compounds in the formation of various heterocyclic compounds such as pyrazines, pyrazinones and imidazolidinones were also illustrated. The thesis further demonstrates the utility of pyrolysis-GC/MS as a powerful analytical tool especially if used in conjunction with isotope labelling techniques. IV Résumé Cette thèse comporte une étude approfondie des routes réactionnelles de la réaction de Maillard dans des systèmes modèles à base d’alanine et de phénylalanine à l’aide de techniques basées sur les principes d’incorporation d’isotopes lourds avec la pyrolyse couplée à la chromatographie phase gazeuse et la spectrométrie de masse (Py-CG/SM) et ainsi que la spectroscopie infrarouge à transformée de Fourier (IR-TF). La formation des glycosylamines par des sucres réducteurs et des acides aminés est un processus bien connu dans la phase initiale de la réaction de Maillard. Ceux-ci jouent un rôle critique dans les étapes de déclenchement et de propagation. Cependant, peu d’attention est orientée vers la capacité de ces imines à subir l'isomérisation et de contribuer à la diversité des produits de la réaction de Maillard. Dans cette étude, l'isomérisation d'imine par la formation du 5-oxazolidinone fut explorée dans des systèmes modèles de phénylalanine/sucre et alanine/sucre. Les preuves spectroscopiques pour la formation du 5-oxazolidinone furent obtenues par la bande intense d'absorption carbonylique centrée à 1784 cm-1 dans le système modèle phénylalanine/glycéraldéhyde et à 1778 cm-1 dans le phénylalanine/glycolaldéhyde. L'importance de la formation du 5-oxazolidinone résulte dans sa capacité à se décarboxyler formant ainsi un ylide d'azomethine ayant l’habileté de produire deux imines isomériques, chacune capable de fabriquer des produits distincts de Maillard. De plus, la formation de tels ylides fut également démontrée par la réaction de leur groupement 1,3-dipolaire avec des dipolarophiles par cycloaddition. Parallèlement, une étude sur le rôle de l'oxygène dans la réaction Maillard, nous a permis de constater que l'oxygène moléculaire peut influencer la rupture des liens carbone-carbone par la formation et la dégradation du 1,2-dioxetane. Ceci dit, le 1,2-dioxetane est formé par les V structures d’énol produits par l’entremise de la réaction de Maillard, à partir de leurs cétones et aldéhydes correspondants tels que le phénylacétaldéhyde, l'aldéhyde de Strecker de la phénylalanine. Il peut aussi être oxydé, produisant ainsi l'aldéhyde benzoïque. En outre, les α-dicarbonyles produits durant la réaction de Maillard jouent un rôle significatif en tant que précurseurs de composés hétérocycliques à effet aromatique important. L’origine de plusieurs de ces composés α-dicarbonyles demeure à ce jour inconnue. En faisant réagir le glucose ou le glyoxal avec de l’alanine isotopiquement marquée ( [13C]- et [15N]- alanine), les mécanismes de la formation du 1,2-butanedione et le 3,4-hexanedione furent confirmés, procédant par l’allongement de chaîne assisté par des acides aminés. De plus, le rôle des α-dicarbonyles dans la formation de divers composés hétérocycliques tels que des pyrazines, des pyrazinones et des imidazolidinones fut aussi étudié. Cette thèse démontre l'utilité de la pyrolyse-CG/SM en tant qu’outil analytique puissant, particulièrement lorsque utilisée en combinaison avec des techniques d'isotopes marqués. VI Statement from the thesis office In accordance with the regulations of the Faculty of Graduate and Postdoctoral studies of McGill University, the following statement from the guidelines for the Thesis preparation is included: Candidates have the option of including, as part of the thesis, the text of one or more papers submitted, or to be submitted, for publication, or the clearly-duplicated text of one or more published papers. These texts must conform to the "Guidelines for Thesis Preparation" and must be bound together as an integral part of the thesis. The thesis must be more than a collection of manuscripts. All components must be integrated into a cohesive unit with a logical progression from one chapter to the next. In order to ensure that the thesis has continuity, connecting texts that provide logical bridges preceding and following each manuscript are mandatory. The thesis must conform to all other requirements of the "Guidelines for Thesis Preparation" in addition to the manuscripts. In general, when co-authored papers are included in a thesis, the candidate must has made a substantial contribution for all papers included in the thesis. In addition, the candidate is required to make an explicit statement in the thesis as to who contributed to such work and to what extent. This statement should appear in a single section entitled "Contributions of Authors" as a preface to the thesis. When previously published copyright
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