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FOODCARBOHYDRATESChemistry, Physical Properties,and ApplicationsCopyright 2005 by Taylor & Francis Group, LLC

Edited bySTEVE W. CUIFOODCARBOHYDRATESChemistry, Physical Properties,and ApplicationsBoca Raton London New York SingaporeA CRC title, part of the Taylor & Francis imprint, a member of theTaylor & Francis Group, the academic division of T&F Informa plc.Copyright 2005 by Taylor & Francis Group, LLC

Published in 2005 byCRC PressTaylor & Francis Group6000 Broken Sound Parkway NW, Suite 300Boca Raton, FL 33487-2742 2005 by Taylor & Francis Group, LLCCRC Press is an imprint of Taylor & Francis GroupNo claim to original U.S. Government worksPrinted in the United States of America on acid-free paper10 9 8 7 6 5 4 3 2 1International Standard Book Number-10: 0-8493-1574-3 (Hardcover)International Standard Book Number-13: 978-0-8493-1574-9 (Hardcover)Library of Congress Card Number 2004058621This book contains information obtained from authentic and highly regarded sources. Reprinted material isquoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable effortshave been made to publish reliable data and information, but the author and the publisher cannot assumeresponsibility for the validity of all materials or for the consequences of their use.No part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic,mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, andrecording, or in any information storage or retrieval system, without written permission from the publishers.For permission to photocopy or use material electronically from this work, please access or contact the Copyright Clearance Center, Inc. (CCC) 222 Rosewood Drive,Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registrationfor a variety of users. For organizations that have been granted a photocopy license by the CCC, a separatesystem of payment has been arranged.Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used onlyfor identification and explanation without intent to infringe.Library of Congress Cataloging-in-Publication DataFood carbohydrates : chemistry, physical properties, and applications / Steve W. Cui, editor.p. cm.Includes bibliographical references and index.ISBN 0-8493-1574-3 (alk. paper)1. Carbohydrates. 2. Food--Carbohydrate content. I. Cui, Steve W.TX553.C28F64 2005664--dc222004058621Visit the Taylor & Francis Web site athttp://www.taylorandfrancis.comTaylor & Francis Groupis the Academic Division of T&F Informa plc.Copyright 2005 by Taylor & Francis Group, LLCand the CRC Press Web site at

1574 Page v Friday, March 25, 2005 2:22 PMPrefaceFood Carbohydrates: Chemistry, Physical Properties, and Applications is intendedas a comprehensive reference book for researchers, engineers, and otherprofessionals who are interested in food carbohydrates. The layout andcontent of the book may be suitable as a reference or text book for advancedcourses on food carbohydrates. The motivation for this book originated froman experience I had six years ago when I was preparing lecture materialsfor a graduate class on food carbohydrates at the Department of Food Science, University of Guelph. After searching several university libraries andthe Internet, I was surprised to find that there was no single book availablein the area of food carbohydrates that could serve the purpose, despitefinding numerous series and monographs found in the library. When I sharedmy observation with colleagues who taught food carbohydrates before orwho are currently teaching the course, all of them agreed with my thoughtthat a comprehensive book covering carbohydrate chemistry and physicalchemistry is in great demand.As an advanced reference book for researchers and other professionals,the aim of this book is not only to provide basic knowledge about foodcarbohydrates, but to put emphasis on understanding the basic principlesof the subject and how to apply the knowledge and techniques in qualitycontrol, product development, and research. There are eight chapters in thebook covering basic chemistry of food carbohydrates (Chapter 1), analyticalmethodologies (Chapter 2), structural analysis of polysaccharides (Chapter3), physical properties (Chapter 4), molecular conformation and characterizations (Chapter 5), and industrial applications of polysaccharide gums(Chapter 6). Chapter 7 is devoted to starch chemistry and functionality, whileChapter 8 presents the most recent developments in starch modification.Emphasis in the last chapter has been given to the reaction principles, andimproved functional properties and practical applications of modifiedstarches.The uniqueness of this book is its broad coverage. For example, it is rareto find analytical methods and structural analysis of polysaccharides in aregular carbohydrate book; however, these two subjects are discussed indetail in this book. The introduction on conformation and conformationanalysis of polysaccharides presented in the book has not been seen in anyother food carbohydrate book. Polysaccharides as stabilizers and hydrocolloids have been described in great detail in several books; the most recentand informative one is the Handbook of Hydrocolloids edited by G.O. Phillipsand P.A. Williams (Woodhead Publishing, 2000). Therefore, the material onpolysaccharide gums (hydrocolloids) introduced in Chapter 6 is brief andCopyright 2005 by Taylor & Francis Group, LLC

1574 Page vi Friday, March 25, 2005 2:22 PMconcise. Information on starch and starch modification is extensive enoughto form separate monographs. The two chapters in this book are concise, butwith the emphasis on understanding the basic principles and applicationsof starches.I would like to acknowledge Dr. Christopher Young for reviewingChapter 3 and Dr. Robin McKellar for proofreading some sections of thebook (both are from the Food Research Program, AAFC, Guelph). My sincerethanks go to Cathy Wang for organizing the references and preparing somefigures and tables for Chapter 3 and Chapter 5. I also would like to thankeach contributor for the hard work and expertise they have contributed tothe book. Lastly, I would like to express my sincere appreciation from thebottom of my heart to my family, Danica, Jennifer (two daughters), andespecially my wife Liqian, for their love, patience, and understanding duringthe course of editing this book.Steve W. CuiCopyright 2005 by Taylor & Francis Group, LLC

1574 Page vii Friday, March 25, 2005 2:22 PMEditorDr. Steve W. Cui is currently a research scientist at the Food ResearchProgram (Guelph, Ontario), Agriculture and Agri-Food Canada, adjunct professor at the Department of Food Science, University of Guelph, and guestprofessor at the Southern Yangtze University (former Wuxi Institute of LightIndustry), Wuxi, China. Dr. Cui is a member of the organizing committee ofthe International Hydrocolloids Conferences and hosted the 6th International Hydrocolloids Conference at Guelph, Canada. He also sits on theeditorial board of Food Hydrocolloids.Dr. Cui’s research interests are on the structure and functional propertiesof hydrocolloids from agricultural products and their applications in foods.His expertise includes extraction, fractionation, analysis of natural polysaccharides, elucidation of polysaccharide structures using methylation analysis, 2D NMR, and mass spectroscopic techniques. He is also interested instudying the structure-function relationship of polysaccharides by examining their conformation, rheological properties, and functionality (as dietaryfiber and stabilizers). He authored a book entitled Polysaccharide Gums fromAgricultural Products: Processing, Structures and Functionality (CRC Press,2000) and edited and co-edited two special issues of Food Hydrocolloids (2003)and a special issue of Trends in Food Science and Technology (Elsevier, 2004)collected from the 6th International Hydrocolloids Conference held inGuelph, Ontario, Canada, in 2002. Dr. Cui holds six patents/patent applications and has published over sixty scientific papers and book chapters in thearea of food carbohydrates. He also gives lectures on food carbohydrates ina biennial graduate course in the Department of Food Science, University ofGuelph, and has delivered several workshops in Asia on structure andfunctionality of food hydrocolloids. He is consulted frequently by researchers and food industries on analytical methods and applications of hydrocolloids in foods and nonfood systems.Dr. Cui graduated from the Peking University (Beijing, China) with a in 1983, from the Southern Yangtze University (Wuxi, China) with aM.Sc. degree in 1986, and from the University of Manitoba (Winnipeg, Manitoba) with a Ph.D. degree in food carbohydrates in 1993.Copyright 2005 by Taylor & Francis Group, LLC

1574 Page ix Friday, March 25, 2005 2:22 PMContributorsYolanda Brummer, M.Sc. Research Technician, Agriculture and Agri-FoodCanada, Guelph, Ontario, CanadaSteve W. Cui, Ph.D. Research Scientist and National Study Leader,Agriculture and Agri-Food Canada and Adjunct Professor, Department ofFood Science, University of Guelph, Ontario, CanadaMarta Izydorczyk, Ph.D. Program Manager, Barley Research, GrainResearch Laboratory, Winnipeg, Manitoba, Canada and Adjunct Professor,Department of Food Science, University of Manitoba, Winnipeg,Manitoba, CanadaQiang Liu, Ph.D. Research Scientist, Agriculture and Agri-Food Canada,Guelph, Ontario, Canada and Adjunct Professor, Department of FoodScience, University of Guelph, Ontario, CanadaQi Wang, Ph.D. Research Scientist, Agriculture and Agri-Food Canada,Guelph, Ontario, Canada and Special Graduate Faculty, Department ofFood Science, University of Guelph, Ontario, CanadaSherry X. Xie, Ph.D. NSERC Visiting Fellow, Agriculture and Agri-FoodCanada, Guelph, Ontario, CanadaCopyright 2005 by Taylor & Francis Group, LLC

1574 Page xi Friday, March 25, 2005 2:22 PMContents1Understanding the Chemistry of Food CarbohydratesMarta Izydorczyk2Understanding Carbohydrate AnalysisYolanda Brummer and Steve W. Cui3Structural Analysis of PolysaccharidesSteve W. Cui4Understanding the Physical Properties of FoodPolysaccharidesQi Wang and Steve W. Cui5Understanding the Conformation of PolysaccharidesQi Wang and Steve W. Cui6Polysaccharide Gums: Structures, Functional Properties,and ApplicationsMarta Izydorczyk, Steve W. Cui, and Qi Wang7Understanding Starches and Their Role in FoodsQiang Liu8Starch Modifications and ApplicationsSherry X. Xie, Qiang Liu, and Steve W. CuiCopyright 2005 by Taylor & Francis Group, LLC

1574 Page 1 Friday, March 25, 2005 2:22 PM1Understanding the Chemistryof Food CarbohydratesMarta IzydorczykCONTENTS1.1 Introduction1.2 Monosaccharides1.2.1 Basic Structure of Monosaccharides1.2.2 Ring Forms of Sugars1.2.3 Stereochemical Transformations1.2.3.1 Mutarotation1.2.3.2 Enolization and Isomerization1.2.4 Conformation of Monosaccharides1.2.4.1 Conformation of the Pyranose Ring1.2.4.2 Conformation of the Furanose Ring1.2.4.3 Determination of Favored Pyranoid Conformation1.2.5 Occurrence of Monosaccharides1.3 Oligosaccharides1.3.1 Formation of Glycosidic Linkage1.3.2 Disaccharides1.3.3 Conformation of Disaccharides1.3.4 Oligosaccharides1.3.5 Cyclic Oligosaccharides1.4 Reaction of Monosaccharides and Derived CarbohydrateStructures1.4.1 Oxidation and Reduction Reactions1.4.2 Deoxy and Amino Sugars1.4.3 Sugar Esters and Ethers1.4.4 Glycosides1.4.5 Browning Reactions1.4.5.1 Maillard Reaction1.4.5.2 CaramelizationCopyright 2005 by Taylor & Francis Group, LLC

1574 Page 2 Friday, March 25, 2005 2:22 PM1.5Polysaccharides1.5.1 General Structures and Classifications1.5.2 Factors Affecting Extractability and Solubility ofPolysaccharides1.5.3 Extraction of Polysaccharides1.5.4 Purification and Fractionation of Polysaccharides1.5.5 Criteria of PurityReferences1.1IntroductionCarbohydrates are the most abundant and diverse class of organic compounds occurring in nature. They are also one of the most versatile materialsavailable and therefore, it is not surprising that carbohydrate-related technologies have played a critical role in the development of new productsranging from foods, nutraceuticals, pharmaceuticals, textiles, paper, and biodegradable packaging materials.1 Carbohydrates played a key role in theestablishment and evolution of life on earth by creating a direct link betweenthe sun and chemical energy. Carbohydrates are produced during the processof photosynthesis:6CO 2 6H 2 O hγ C6H12 O 6 6O 2Carbohydrates are widely distributed both in animal and plant tissues,where they function as: Energy reserves (e.g., starch, fructans, glycogen). Structural materials (e.g., cellulose, chitin, xylans, mannans). Protective substances. Some plant cell wall polysaccharides are elicitors of plant antibiotics (phytoalexins). In soybean, fragments ofpectic polysaccharides (α-4-linked dodecagalacturonide) inducesynthesis of a protein (protein inhibitor inducer factor) that inhibitsinsect and microbial proteinases. Arabinoxylans have been postulatedto inhibit intercellular ice formation, thus ensuring winter survivalof cereals. Cell recognition moieties. Oligosaccharides conjugated to protein(glycoproteins) or to lipids (glycolipids) are important componentsof cell membranes and can be active in cell to cell recognition andsignalling. It is recognized that oligosaccharide moieties serve asprobes through which the cell interacts with its environment. Inaddition, the environment delivers signals to the interior of the cellthrough the cell surface oligosaccharides. Information transfer agents (nucleic acids).Copyright 2005 by Taylor & Francis Group, LLC

1574 Page 3 Friday, March 25, 2005 2:22 PMUnderstanding the Chemistry of Food Carbohydrates3The first carbohydrates studied contained only carbon (C), hydrogen (H),and oxygen (O), with the ratio of H:O the same as in water, 2:1, hence thename carbohydrates or hydrates of carbon, Cx(H2O)y, was given. The composition of some carbohydrates is indeed captured by the empirical formula,but most are more complex. According to a more comprehensive definitionof Robyt (1998),2 carbohydrates are polyhydroxy aldehydes or ketones, orcompounds that can be derived from them by: Reduction of the carbonyl group to produce sugar alcohols Oxidation of the carbonyl group and/or hydroxyl groups to sugaracids Replacement of one or more of the hydroxyl moieties by variouschemical groups, e.g., hydrogen (H) to give deoxysugars, aminogroups (NH2 or acetyl-NH2) to give amino sugars Derivatization of the hydroxyl groups by various moieties, e.g.,phosphoric acid to give phosphosugars, sulphuric acid to give sulphosugars Their polymers having polymeric linkages of the acetal typeFood carbohydrates encompass a wide range of molecules and can beclassified according to their chemical structure into three main groups: Low molecular weight mono- and disaccharides Intermediate molecular weight oligosaccharides High molecular weight polysaccharidesNutritionists divide food carbohydrates into two classes:3 Available, or those which are readily utilized and metabolized. Theymay be either mono-, di-, oligo- or polysaccharides, e.g., glucose,fructose, sucrose, lactose, dextrins, starch. Unavailable, or those which are not utilized directly but insteadbroken down by symbiotic bacteria, yielding fatty acids, and thusnot supplying the host with carbohydrate. This includes structuralpolysaccharides of plant cell walls and many complex polysaccharides, e.g., cellulose, pectins, beta-glucans. Structure of MonosaccharidesMonosaccharides are chiral polyhydroxy aldehydes and polyhydroxyketones that often exist in cyclic hemiacetal forms. As their name indicates,Copyright 2005 by Taylor & Francis Group, LLC

1574 Page 4 Friday, March 25, 2005 2:22 PM4Food Carbohydrates: Chemistry, Physical Properties, and ApplicationsTABLE 1.1Classification of MonosaccharidesNumber ofCarbonAtoms3456789Kind of Carbonyl emonosacharides are monomeric in nature and cannot be depolymerized byhydrolysis to simpler sugars. Monosaccharides are divided into two majorgroups according to whether their acyclic forms possess an aldehyde or aketo group, that is, into aldoses and ketoses, respectively. These, in turn, areeach classified according to the number of carbons in the monosaccharidechain (usually 3 to 9), into trioses (C3), tetroses (C4), pentoses (C5), hexoses(C6), heptoses (C7), octoses (C8), nonoses (C9). By adding the prefix aldo- tothese names, one can define more closely a group of aldoses, e.g., aldohexose,aldopentose. For ketoses it is customary to add the ending -ulose (Table 1.1).Various structural diagrams are available for representing the structuresof sugars.2,4 The system commonly used for linear (acyclic) monosaccharidesis the Fischer projection formula, named after the famous scientist, EmilHerman Fischer (1852 to 1919), which affords an unambiguous way to depictsugar molecules (Figure 1.1), provided the following rules are followed: The carbon chain is drawn vertically, with the carbonyl group at thetop, and the last carbon atom in the chain, i.e., the one farthest fromthe carbonyl group, at the bottom. All vertical lines represent the (C–C) bonds in the chain lying belowan imaginary plane (vertical lines represent bonds below the plane),and all horizontal lines actually represent bonds above the plane. The numbering of the carbon atoms in monosaccharides alwaysstarts from the carbonyl group or from the chain end nearest to thecarbonyl group (Figure 1.1).Formally, the simplest monosaccharide is the three-carbon glyceraldehyde(aldotriose) (Figure 1.1). It has one asymmetric carbon atom (chiral centre)and consequently, it has two enantiomeric forms. Using traditional carbohydrate nomenclature, the two forms are D- and L-glyceraldehydes.5 A chiralatom is one that can exist in two different spatial arrangements (configurations). Chiral carbon atoms are those having four different groups attachedto them. The two different arrangements of the four groups in space arenonsuperimposable mirror images of each other.Copyright 2005 by Taylor & Francis Group, LLC

1574 Page 5 Friday, March 25, 2005 2:22 PMUnderstanding the Chemistry of Food eraldehydeL-glyceraldehydeFIGURE 1.1Structures of D-glyceraldehyde and L-glyceraldehyde.These two compounds have the same empirical formula, C3H6O3, but aredistinct, having different chemical and physical properties. For instance,D-glyceraldehyde rotates the plane polarized light to the right ( ) and has aspecific optical rotation ([α]D) at 25 C of 8.7 ; whereas L-glyceraldehyderotates the plane polarized light to the left (-) and has a different specificoptical rotation, [α]D, at 25 C of –8.7 . Carbon C-2 in glyceraldehyde corresponds to the chiral centre. If the OH group attached to the highest numberedchiral carbon is written to the right in the vertical structure as shown above,a sugar belongs to the D-chiral family; if the OH is written to the left, a sugarbelongs to the L-chiral family. Since the principal purpose of the D and Lsymbols is to distinguish between chiral families of sugars, the structuralspecification should, in fact, be consistent with modern nomenclature of theInternational Union of Pure and Applied Chemistry (IUPAC): R (Latin, rectus, right) should be used instead of D. S (Latin, sinister, left) instead of L.The higher aldoses belongin

Food Carbohydrates: Chemistry, Physical Properties, and Applications is intended as a comprehensive reference book for researchers, engineers, and other professionals who are interested in food carbohydrates. The layout and content of the book may be suitable as a reference or text book for advanced courses on food carbohydrates.

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