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Investigation of Immunogenic Gluten Peptides

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Investigation of Immunogenic Gluten Peptides Investigation of Immunogenic Gluten Peptides: Identification Using Enzymatic Tagging and HPLC-MS n; Analysis and Quantification Using HPLC-MS/MS Jennifer A. Sealey-Voyksner A dissertation submitted to the faculty of the University of North Carolina at Chapel Hill in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Department of Chemistry. Chapel Hill 2009 Approved by: Advisor: Professor James W. Jorgenson Professor Gary L. Glish Professor Mark H. Schoenfisch Professor Gary J. Pielak Professor Susan T. Lord © 2009 Jennifer A. Sealey-Voyksner ALL RIGHTS RESERVED ii ABSTRACT Jennifer A. Sealey-Voyksner: Investigation of Immunogenic Gluten Peptides: Identification Using Enzymatic Tagging and HPLC-MS n; Analysis and Quantification Using HPLC-MS/MS (Under the direction of Dr. James W. Jorgenson) The goal of my research was to provide some insight into a widely appreciated but poorly understood relationship between cereal grain proteins and human health. My research objectives were: (1) to identify and characterize inflammatory, physiologically relevant, wheat gluten peptides and (2) to develop a unique analytical methodology to screen commercially available food and consumer products for the quantitative detection of these peptides. Gluten proteins comprise a very large protein family found in cereal grain seeds. This large protein family consists of hundreds of proteins ranging in size from about 30 kDa into the millions of KDa. Today’s nomenclature refers to “gluten” as the water-insoluble seed storage proteins found in the Triticeae tribe of the grass (Gramineae) family that includes wheat, rye and barley. Some gluten proteins associated with grains in the Triticeae tribe (specifically: wheat, rye and barley), have been implicated in various autoimmune diseases, food allergies, intolerances and are important factors in several inflammatory diseases. Many analytical techniques have been used to study gluten proteins and peptides. Unambiguous identification and structural characterization of such iii peptides is a necessary step toward an eventual understanding of their chemical biology. Liquid chromatography-mass spectrometry (LC-MS) is an extremely powerful tool for such analyses. Results of my research are presented here, in the following chapters of this thesis report. Data presented supports the development of a novel and effective analytical methodology, using enzymatic/chemical labeling chemistry and HPLC/MS n; to identify and characterize seven physiologically relevant wheat gluten peptides. A sensitive and specific assay was then developed for the quantitative detection of these peptides via direct in-vitro proteolytic digestion and HPLC-MS/MS. This versatile methodology allows both processed and native foods, as well as consumer products, to be analyzed for the presence of wheat gluten. Continued efforts in this area will pave the way for eventual commercial application, as a service to both the celiac community and the food industry, by providing an accurate and economic means to generate much needed data for researchers developing treatments for patients with gluten sensitivities and manufacturers producing and labeling products that are safe. iv ACKNOWLEDGEMENTS I would like to thank my advisor, Dr. James Jorgenson, for his support and encouragement. I would also like to thank Dr. Chaitan Khosla and the Celiac Sprue Research Foundation for their guidance as well as assistance with experiments, which were invaluable to the success of this research project. My husband, Robert, deserves volumes to be written about him. He has supported, inspired, mentored, taught as well as patiently and unconditionally loved me throughout this academic adventure. From the first moment that I asked his advice on the notion of going back to school to achieve a Ph.D, to introducing me to my future advisor, Dr. James Jorgenson; to helping me understand electronics; to teaching me how to better interpret mass spectra and mass spectrometers; to drying the tears of frustration; to brainstorming about the experimental design and interpretation of the data at 3am and on the road to the beach and in the air to yet another meeting and even over a glass of wine on our much treasured date nights; to never being too busy to review manuscripts, posters and presentations; to constantly reminding me to back up my data; to making me re-re-re-work the concentration calculations; to tirelessly trying to make me believe in myself; Robert has and always will be my knight: I love him and will be eternally grateful to him. My sincere gratitude goes out to many of my friends, especially my dear friend Roger Mercer. Roger first inspired me as a young scientist, then truly supported, mentored and encouraged me to pursue this daunting personal goal. Lastly, I appreciate the love and support of my parents and especially that of my brother, who has given me an unending supply of R.A.I.S.E. and ehugs. v TABLE OF CONTENTS Page LIST OF TABLES .................................................................................................... xiv LIST OF FIGURES ................................................................................................. xvi LIST OF ABBREVIATIONS ................................................................................... xxv LIST OF SYMBOLS ............................................................................................... xxx CHAPTERS: Chapter 1 Introduction to Gluten and Celiac Disease .......................................... 1 1.1 What is gluten? ......................................................................... 1 1.1.1 Wheat gluten protein nomenclature and composition .............................................................. 4 1.2 Link between gluten and human disease .................................. 6 1.3 Celiac disease .......................................................................... 7 1.3.1 The genetic factor ..................................................... 8 1.3.2 The gluten factor ....................................................... 9 1.3.3 The immunological factor ........................................ 11 1.3.3.1 Adaptive immune response to gluten ..... 12 1.3.3.2 Innate immune response to gluten ......... 13 1.3.4 Other environmental factors ................................... 13 1.4 Motivation for measuring gluten .............................................. 14 1.5 Methods of gluten measurement ............................................ 15 vi 1.5.1 Measurement of gluten using HPLC-MS ................ 17 1.5.1.1 Ion trap mass spectrometer .................... 18 1.5.1.2 Triple quadrupole mass spectrometer .... 19 1.6 Overview of this thesis report .................................................. 20 1.6.1 Chapter 2 ................................................................ 20 1.6.2 Chapter 3 ................................................................ 21 1.6.3 Chapter 4 ................................................................ 21 1.6.4 Chapter 5 ................................................................ 22 1.6.5 Chapter 6 ................................................................. 23 1.7 References ............................................................................. 33 Chapter 2 Use of In-Vitro Enzymatic Digestion and Metal Ion Attachment to Selectively Study and Identify Potential Immunogenic Gluten Peptides using HPLC-MS n ................................................................ 38 2.1 Introduction ............................................................................. 38 2.1.1 In-vitro enzymatic digestion of gluten proteins ........ 39 2.1.2 Metal ion attachment .............................................. 40 2.2 Experimental ........................................................................... 41 2.2.1 Materials and reagents ........................................... 41 2.2.1.1 Expression and purification of recombinant prolyl endopeptidase .......... 41 2.2.1.2 Isolation of brush border membrane enzymes ................................................. 42 2.2.1.3 Chemicals and samples .......................... 42 2.2.2 Enzymatic digestion of wheat gluten flour ............... 42 2.2.2.1 Treatment with gastric and pancreatic enzymes ................................................. 42 vii 2.2.2.2 Treatment with prolyl endopeptidase ...... 43 2.2.2.3 Treatment with brush border membrane enzymes ................................................. 44 2.2.2.4 Sample preparation for LC-MS analysis . 44 2.2.3 HPLC-MS n analysis ................................................. 44 2.2.3.1 Enzymatic digestion analysis .................. 44 2.2.3.2 Metal ion analysis ................................... 45 2.3 Results and Discussion .......................................................... 46 2.3.1 In-vitro enzymatic digestion of wheat gluten ........... 46 2.3.2 Metal ion affinity for proline ..................................... 49 2.3.2.1 Determining metal affinity for proline ...... 49 2.3.2.2 Sequence information about gluten peptides using metal ion-adducts ........... 52 2.4 Conclusions ............................................................................ 55 2.5 References ............................................................................. 73 Chapter 3 Identification of Immunogenic Wheat Gluten Peptides Based on Enzymatic Tagging and HPLC-UV-Fluorescence and-MS n .............. 74 3.1 Introduction ............................................................................
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