SPRINGER BRIEFS IN MOLECULAR SCIENCE CHEMISTRY OF FOODS Dongliang Ruan Hui Wang Faliang Cheng The Maillard Reaction in Food Chemistry Current Technology and Applications SpringerBriefs in Molecular Science Chemistry of Foods Series editor Salvatore Parisi, Industrial Consultant, Palermo, Italy The series Springer Briefs in Molecular Science: Chemistry of Foods presents compacttopicalvolumesintheareaoffoodchemistry.Theserieshasaclearfocus on the chemistry and chemical aspects of foods, topics such as the physics or biology offoods are not part of its scope. The Briefs volumes in the series aim at presenting chemical background information or an introduction and clear-cut overviewonthechemistryrelatedtospecifictopicsinthisarea.Typicaltopicsthus include: – Compound classes in foods—their chemistry and properties with respect to the foods (e.g. sugars, proteins, fats, minerals, …) – Contaminants and additives in foods—their chemistry and chemical transformations – Chemical analysis and monitoring offoods – Chemical transformations in foods, evolution and alterations of chemicals in foods, interactions between food and its packaging materials, chemical aspects of the food production processes – Chemistry and the food industry—from safety protocols to modern food production The treated subjects will particularly appeal to professionals and researchers concerned with food chemistry. Many volume topics address professionals and current problems in the food industry, but will also be interesting for readers generally concerned with the chemistry of foods. With the unique format and characterofSpringerBriefs(50to125pages),thevolumesarecompactandeasily digestible. Briefs allow authors to present their ideas and readers to absorb them withminimaltimeinvestment.BriefswillbepublishedaspartofSpringer’seBook collection,withmillionsofusersworldwide.Inaddition,Briefswillbeavailablefor individual print and electronic purchase. Briefs are characterized by fast, global electronic dissemination, standard publishing contracts, easy-to-use manuscript preparation and formatting guidelines, and expedited production schedules. Both solicitedandunsolicitedmanuscriptsfocusingonfoodchemistryareconsideredfor publication in this series. More information about this series at http://www.springer.com/series/11853 Dongliang Ruan Hui Wang (cid:129) Faliang Cheng The Maillard Reaction in Food Chemistry Current Technology and Applications 123 Dongliang Ruan Faliang Cheng DongguanUniversity of Technology DongguanUniversity of Technology Dongguan,Guangdong, China Dongguan,Guangdong, China HuiWang Lacombe Research Centre Agriculture andAgri-FoodCanada Lacombe,AB, Canada ISSN 2191-5407 ISSN 2191-5415 (electronic) SpringerBriefs inMolecular Science ISSN 2199-689X ISSN 2199-7209 (electronic) Chemistry of Foods ISBN978-3-030-04776-4 ISBN978-3-030-04777-1 (eBook) https://doi.org/10.1007/978-3-030-04777-1 LibraryofCongressControlNumber:2018962133 ©TheAuthor(s),underexclusivelicensetoSpringerNatureSwitzerlandAG2018 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpart of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission orinformationstorageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilar methodologynowknownorhereafterdeveloped. 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ThisSpringerimprintispublishedbytheregisteredcompanySpringerNatureSwitzerlandAG Theregisteredcompanyaddressis:Gewerbestrasse11,6330Cham,Switzerland Preface Maillardreaction,thewell-knownnon-enzymaticreactionbetweenreducingsugars andproteins,isoneofthemostimportantreactionsinfoodsciences.Aminoacids, peptidesandproteinsarethekeyconstituentsoffoodandalsodirectlycontributeto the changes in colour, flavor, and nutritive value but also for the formation of stabilizing and mutagenic compounds during thermal or enzymatic reactions in production,processingandstorageoffood.Proteinsalsocontributesignificantlyto thephysicalpropertiesoffoodthroughtheirabilitytobuildorstabilizegels,foams and emulsions properties. Due to the complexity of the Maillard reaction, mass spectrometry(MS)isausefulandpowerfultechnologytocharacterizetheMaillard reaction products and we have apply MS-based technologies to systematically investigate Maillard reaction from amino acids, peptides, proteins, to characterize the Maillard reaction products and to identify the modification sites of proteins. Studies demonstrate that glucosylation increased emulsification activity index and emulsifyingstabilityindex.ThepresentinvestigationdemonstratesthatMS-related technologies are important tools to analyze and characterize the Maillard reaction products and functional properties offood proteins. Dongguan, China Dongliang Ruan Lacombe, Canada Hui Wang Dongguan, China Faliang Cheng v Acknowledgements The authors would like to thank Prof. C. Y. Ma and Dr. Ivan K. Chu for their invaluable advices, constant encouragement and inspiring discussion during the studies and writing process. The authors would like to thank Prof. Michael Siu, Dr. Wang Mingfu, Dr. K. H. Sze and Dr. Huang Junchao for their stimulating discussion and helpful comments in the research. The authors would like to thank my friends, colleagues and members of our laboratories for reading and comments on chapters: Dr. Siu Shiu On, Dr. Emily Choi, Dr. Song Tao, Dr. Edward Lau and Dr. Corey N. W. Lam for the valuable friendship, help and support. The authors would like to express my appreciation to all the staff and technical servicecrewintheSchoolofBiologicalScienceandtheChemistryDepartment,the University of Hong Kong. Finally, the authors would like to dedicate the whole-heart thanks to Hui, Irene and Max, and all the family members for their love, care and understanding throughout my research. vii Contents 1 The Maillard Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.2 The Maillard Reaction and Food Properties . . . . . . . . . . . . . . . . 2 1.3 The Chemistry of the Maillard Reaction. . . . . . . . . . . . . . . . . . . 2 1.4 Conditions Affecting the Maillard Reaction . . . . . . . . . . . . . . . . 5 1.5 The Analysis of MRPs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7 1.5.1 ESI-MS and MALDI-TOF-MS. . . . . . . . . . . . . . . . . . . . 8 1.5.2 MS Characterization of ARPs. . . . . . . . . . . . . . . . . . . . . 9 1.5.3 Protein Glycation and Glycation Site Analysis. . . . . . . . . 10 1.6 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 12 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13 2 Characterization of the Maillard Reaction in Amino Acid–Sugar Systems . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23 2.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23 2.2 MS Analysis of Amino Acid–Sugar System. . . . . . . . . . . . . . . . 23 a 2.3 Structure Determination of Glucosylated N -Acetyl-Lysine by Nuclear Magnetic Resonance (NMR) Spectroscopy . . . . . . . . 25 2.4 ARPs in Amino Acid–Sugar Systems . . . . . . . . . . . . . . . . . . . . 28 2.4.1 MS/MS of ARPs with D-Glucose . . . . . . . . . . . . . . . . . . 28 2.4.2 MS/MS of ARPs with Disaccharides. . . . . . . . . . . . . . . . 28 2.5 MS/MS and MS3 of ARPs . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30 2.6 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32 3 Characterization of Glycated Lysine in Peptide–Sugar System. . . . . 33 3.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 3.2 Solid-Phase Peptide Synthesis (SPPS) . . . . . . . . . . . . . . . . . . . . 34 3.2.1 Synthesis Procedure. . . . . . . . . . . . . . . . . . . . . . . . . . . . 34 3.2.2 Cleavage of the Peptide . . . . . . . . . . . . . . . . . . . . . . . . . 35 ix x Contents 3.3 ESI-MS Analysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35 3.4 Effects of the Maillard Reaction . . . . . . . . . . . . . . . . . . . . . . . . 35 3.5 Fragmentation Sugar Moieties . . . . . . . . . . . . . . . . . . . . . . . . . . 36 3.6 Fragmentation of Peptide Moieties. . . . . . . . . . . . . . . . . . . . . . . 43 3.6.1 Fragmentation of [M-84+H]+ . . . . . . . . . . . . . . . . . . . . . 43 3.6.2 MS3 of Glucosylated Di-peptides . . . . . . . . . . . . . . . . . . 45 3.6.3 MS3 Spectra of [M-84+H]+ from Glucosylated Tri-Peptides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46 3.7 Fragmentation of Lysine-Containing Tetra-Peptides . . . . . . . . . . 49 3.8 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53 4 Determination of the Maillard Reaction Sites and Properties’ Effects of Lysozyme . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55 4.1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55 4.2 Sample Preparation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56 4.3 MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57 4.3.1 MALDI-TOF-MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57 4.3.2 MALDI-TOF/TOF-MS. . . . . . . . . . . . . . . . . . . . . . . . . . 57 4.3.3 Nano-LC-QqTOF-MS . . . . . . . . . . . . . . . . . . . . . . . . . . 57 4.4 Emulsifying Properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58 4.5 Differential Scanning Calorimetry (DSC) . . . . . . . . . . . . . . . . . . 59 4.6 Deconvolution of ESI-MS Spectra. . . . . . . . . . . . . . . . . . . . . . . 60 4.7 MS Analysis of Intact Lysozyme. . . . . . . . . . . . . . . . . . . . . . . . 60 4.8 Effects of Glucosylation on Lysozyme. . . . . . . . . . . . . . . . . . . . 65 4.8.1 Effect on Emulsifying Properties. . . . . . . . . . . . . . . . . . . 65 4.8.2 Effect on Thermal Properties . . . . . . . . . . . . . . . . . . . . . 67 4.9 Characterization of Glycation of Lysozyme . . . . . . . . . . . . . . . . 68 4.9.1 MALDI-TOF-MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 68 4.9.2 MALDI-TOF/TOF-MS. . . . . . . . . . . . . . . . . . . . . . . . . . 72 4.9.3 Nano-LC-MS/MS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73 4.10 Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 79 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80 Abbreviations 12-crown-4 1,4,7,10-tetraacyclododecane ACN Acetonitrile CID Collision induced dissociation ECD Electron capture dissociation EI Electron impact ESI Electrospray ESI* Emulsifying stability index ETD Electron transfer dissociation eV Electron voltage FAB Fast atom bombardment FTICR Fourier transform ion cyclotron resonance GC Gas chromatography HPLC High pressure/performance liquid chromatography HRP Horseradish peroxidase LIT Linear ion trap m/z Mass to charge ratio MALDI Matrix-assisted laser desorption/ionization MeOH Methanol MS Mass spectrometry MS2 or MS/MS Tandem mass spectrometry MSn Multistage tandem mass spectrometry NMR Nuclear magnetic resonance NP Normal phase PMF Peptide mass fingerprint PNGaseF Peptide N-glycosidase F PTMs Posttranslational modifications Q Quadrupole QIT Quadrupole ion trap QqQ Triple quadrupole RNaseB Ribonuclease B xi