DOCSLIB.ORG

General Biochemistry Chemistry of Polysaccharides

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
General Biochemistry Chemistry of Polysaccharides General Biochemistry BIOC 201 Chapter IV Chemistry of Polysaccharides Objectives 11.. The main objective of this chapter is getting the student to know the polysaccharides constituents of human food. 22. The chapter is designed to familiarize the student with the basic biochemical classification of polysaccharides. 33.. To provide the student with the occurrence of different polysaccharides in nature. Most carbohydrates found in nature occur as polysaccharide polymers of medium to high molecular weight. Polysaccharides, also called glycans They differ from each other in: the identity of their monosaccharide units in the length of their chains in the types of bonds linking the units and in the degree of branching Polysaccharides Homopolysaccharides Heteropolysaccharides (same sugar units) (sugar units + other groups) Homopolysaccharides (same sugar units) Glucosans Fructosans Only glucose Only fructose Starch, Dextrin Inulin Glycogen, Cellulose Heteropolysaccharides (sugar units + other groups) Neutral Acidic Some Homopolysaccharides Are Stored Forms of Fuel Starch and dextrin * present only in plants. * formed of thousands of D-glucose units linked by α 1-4 and α 1-6 glucosidic linkage. (Branched) Glycogen is the main storage in humans (Liver and Muscles ) Glycogen and starch ingested in the diet are hydrolyzed by α amylases , enzymes in saliva and intestinal secretions that break (α 1-4 ) glycosidic bonds between glucose units. Most animals cannot use cellulose as a fuel source, because they lack an enzyme to hydrolyze the (β 1- 4 ) linkages. Dextrans are bacterial and yeast polysaccharides made up of (α 1-6 )-linked poly-D-glucose; all have (α 1-3) branches, and some also have ( α 1-2) or (α 1-4) branches. Dental plaque , formed by bacteria growing on the surface of teeth, is rich in dextrans. Some Homopolysaccharides Serve Structural Roles Cellulose , a fibrous, tough, water-insoluble substance, is found in the cell walls of plants. Cellulose constitutes much of the mass of wood, and cotton is almost pure cellulose. The cellulose molecule is a linear, unbranched homopolysaccharide, consisting of 10,000 to 15,000 D-glucose units. Cellulose cont., In cellulose the glucose residues have the β configuration Not digested in our gut Stimulate intestinal peristalsis and prevent constipation Amylopectin Cellulose breakdown by fungi Chitin Chitin is a linear homopolysaccharide composed of N-acetylglucosamine residues in β linkage The only chemical difference from cellulose is the replacement of the hydroxyl group at C-2 with an acetylated amino group Chitin Chitin forms extended fibers similar to those of cellulose, and like cellulose cannot be digested by vertebrates Chitin is the principal component of the hard exoskeletons of nearly a million species of arthropods, insects, lobsters, and crabs, for example and is probably the second most abundant polysaccharide, next to cellulose, in nature Chitin Inulin is a homopolysaccharide of fructose (fructosan ) found in tubers and roots of artichokes. It is readily soluble in water. Heteropolysaccharides Heteropolysaccharides provide extracellular support for organisms of all kingdoms. Rigid layer of the bacterial cell envelope (the peptidoglycan ) Peptidoglycan Peptidoglycan confers mechanical support and prevents bacteria from bursting in response to their high internal osmotic pressure. Heteropolysaccharides (sugar units + other groups) (Mucopolysaccharide) Neutral Acidic Mucopolysaccharides Complex carbohydrates characterized by their content of amino sugars and uronic acids. When attached to a protein molecule, the result is a proteoglycan. Proteoglycans provide the ground or packing substance of connective tissues. Neutral Mucopolysaccharides Almost all the plasma proteins of humans except albumin are glycoproteins . A number of the blood group substances are glycoproteins, whereas others are glycosphingolipids. Antigens, eg, ABO blood group substances are Neutral Mucopolysaccharides Acidic Mucopolysaccharides Sulfate free ( Hyaluronic acid )) Ground substance of connective tissues Hydrolysis = acetic acid, glucosamine & glucuronic acid Sulfate containing Acidic Mucopolysaccharides Chnodroitin sulfate contributes to the tensile strength of cartilage, tendons, ligaments, and the walls of the aorta. (Cartilages and bones) Hydrolysis = acetic acid Galactose amine Sulfuric acid Glucuronic acid Sulfate containing Acidic Mucopolysaccharides Heparin is a natural anticoagulant made in mast cells (a type of leukocyte) Released into the blood, where it inhibits blood coagulation by binding to the protein antithrombin and inhibit thrombin, a protease essential to blood clotting. Hydrolysis = glucosamine Sulfuric acid Glucuronic acid.
Load more

Recommended publications
  • Structure-Function Relationships of Glucansucrase and Fructansucrase Enzymes from Lactic Acid Bacteria Sacha A
    MICROBIOLOGY AND MOLECULAR BIOLOGY REVIEWS, Mar. 2006, p. 157–176 Vol. 70, No. 1 1092-2172/06/$08.00ϩ0 doi:10.1128/MMBR.70.1.157–176.2006 Copyright © 2006, American Society for Microbiology. All Rights Reserved. Structure-Function Relationships of Glucansucrase and Fructansucrase Enzymes from Lactic Acid Bacteria Sacha A. F. T. van Hijum,1,2†* Slavko Kralj,1,2† Lukasz K. Ozimek,1,2 Lubbert Dijkhuizen,1,2 and Ineke G. H. van Geel-Schutten1,3 Centre for Carbohydrate Bioprocessing, TNO-University of Groningen,1 and Department of Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen,2 9750 AA Haren, The Netherlands, and Innovative Ingredients and Products Department, TNO Quality of Life, Utrechtseweg 48 3704 HE Zeist, The Netherlands3 INTRODUCTION .......................................................................................................................................................157 NOMENCLATURE AND CLASSIFICATION OF SUCRASE ENZYMES ........................................................158 GLUCANSUCRASES .................................................................................................................................................158 Reactions Catalyzed and Glucan Product Synthesis .........................................................................................161 Glucan synthesis .................................................................................................................................................161 Acceptor reaction ................................................................................................................................................161
    [Show full text]
  • Polysaccharides
    Polysaccharides: Homopolysaccharide Heteropolysaccharide Glucose is the most common monomer Mostly homo, however, if hetero, it will be two monosaccharides in a repeating sequence Complete characterization of a polysaccharide: monomers, sequence & type of glycosidic linkage Cellulose & chitin: β-glycosidic linkages, and both are structural materials Starch and glycogen: α-glycosidic linkages, and they serve as carbohydrate storage polymers in plants and animals, respectively The major structural component of plants, especially wood and plant fibers A linear polymer of approximately 2800 D-glucose units per molecule joined by β-1,4-glycosidic bonds Extensive intra- and intermolecular hydrogen bonding between chains Cellulases, animals? Energy storage in plants A polymers of α-D-glucose units A mylose (10-20 %): continuous, unbranched chains of up to 4000 α-D-glucose units joined by α-1,4-glycosidic bonds Amylopectin (80-90 %): a highly branched polymer consisting of 24-30 units of D-glucose joined by α-1,4- glycosidic bonds and branches created by α- 1,6-glycosidic bonds Amylases catalyze hydrolysis of α-1,4-glycosidic bonds β-amylase is an exoglycosidase and cleaves from the non- reducing end of the polymer α-amylase is an endoglycosidase and hydrolyzes glycosidic linkages anywhere along the chain to produce glucose and maltose Can amylose & amylopectin be completely degraded to glucose and maltose by the two amylases? Debranching enzymes catalyze the hydrolysis of α-1,6-glycosidic bonds A branched-chain polymer of
    [Show full text]
  • Bio-Based Polymer Electrolytes for Electrochemical Devices: Insight Into the Ionic Conductivity Performance
    materials Review Bio-Based Polymer Electrolytes for Electrochemical Devices: Insight into the Ionic Conductivity Performance Marwah Rayung 1, Min Min Aung 1,2,* , Shah Christirani Azhar 2, Luqman Chuah Abdullah 3 , Mohd Sukor Su’ait 4, Azizan Ahmad 4,5 and Siti Nurul Ain Md Jamil 2 1 Institute of Tropical Forestry and Forest Products, Universiti Putra Malaysia, Serdang 43400, Malaysia; [email protected] 2 Unit Chemistry, Center of Foundation Studies and Agricultural Science, Universiti Putra Malaysia, Serdang 43400, Malaysia; [email protected] (S.C.A.); [email protected] (S.N.A.M.J.) 3 Department of Chemical and Environmental Engineering, Faculty of Engineering, Universiti Putra Malaysia, Serdang 43400, Malaysia; [email protected] 4 Solar Energy Research Institute (SERI), Universiti Kebangsaan Malaysia, Bangi 43600, Malaysia; [email protected] (M.S.S.); [email protected] (A.A.) 5 School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, Bangi 43600, Malaysia * Correspondence: [email protected] Received: 10 October 2019; Accepted: 4 December 2019; Published: 12 February 2020 Abstract: With the continuing efforts to explore alternatives to petrochemical-based polymers and the escalating demand to minimize environmental impact, bio-based polymers have gained a massive amount of attention over the last few decades. The potential uses of these bio-based polymers are varied, from household goods to high end and advanced applications. To some extent, they can solve the depletion and sustainability issues of conventional polymers. As such, this article reviews the trends and developments of bio-based polymers for the preparation of polymer electrolytes that are intended for use in electrochemical device applications.
    [Show full text]
  • Carbohydrate Naturally Occurring Polysaccharide in Food Sea Weed Polysaccharide Sources And
    Carbohydrate Naturally occurring polysaccharide in food sea weed polysaccharide sources and use Carbohydrate- • Carbohydrates are commonly called as sugars - composed of C, H and O • Term saccharide is derived from the Latin word “sacchararum" from the sweet taste of sugars. • Compounds like glucose, fructose, starch and cellulose are called as carbohydrates. • types - Monosaccharides, Disaccharides and Polysaccharides • Monosaccharides are the simplest form of carbohydrate and contain different classes such as Trioses, Tetroses, etc. CARBOHYDRATE: • “The organic compounds which yield polyhydric aldehyde or ketone on hydrolysis are called as carbohydrates.” • empirical formula as (CH2O)n. • The name "carbohydrate" means a "hydrate of carbon.“ • For example glucose is written,C6H12O6. CLASSIFICATION OF CARBOHYDRATE A) Monosaccharides B) Oligosaccharides C) Polysaccharides - Homopolysaccharides and Heteropolysaccharides MONOSACCHARIDES: • They are simplest group of carbohydrate which cannot be hydrolyzed into simplest sugar. • They are divided into different classes on the basis of number of carbon atoms present in it like TRIOSES, TETROSES, PENTOSES etc. OLIGOSACCHARIDES: • They are formed by the condensation of a few monosaccharide units (2-10) • During the union of monosaccharide units water molecule is eliminated and the remaining units are linked through an oxygen bridge called as glycosides bond • They are being divided into Disaccharide and Trisaccharides. • DISACCHARIDE – SUCROSE, MALTOSE, LACTOSE Polysaccharides • Polysaccharides
    [Show full text]
  • 7 | Carbohydrates and Glycobiology
    7 | Carbohydrates and Glycobiology Aldoses and Ketoses; Representative monosaccharides. (a)Two trioses, an aldose and a ketose. The carbonyl group in each is shaded. • An aldose contains an aldehyde functionality • A ketose contains a ketone functionality The Glycosidic Bond • Two sugar molecules can be joined via a glycosidic bond between an anomeric carbon and a hydroxyl carbon • The glycosidic bond (an acetal) between monomers is less reactive than the hemiacetal at the second monomer – Second monomer, with the hemiacetal, is reducing – Anomeric carbon involved in the glycosidic linkage is nonreducing • The disaccharide formed upon condensation of two glucose molecules via 1 4 bond is called maltose • Formation of maltose. A disaccharide is formed from two monosaccharides (here, two molecules of D-glucose) when an —OH (alcohol) of one glucose molecule (right) condenses with the intramolecular hemiacetal of the other glucose molecule (left), with elimination of H2O and formation of a glycosidic bond. The reversal of this reaction is hydrolysis—attack by H2O on the glycosidic bond. The maltose molecule, shown here as an illustration, retains a reducing hemiacetal at the C-1 not involved in the glycosidic bond. Because mutarotation interconverts the α and β forms of the hemiacetal, the bonds at this position are sometimes depicted with wavy lines, as shown here, to indicate that the structure may be either α or β. Nonreducing Disaccharides • Two sugar molecules can be also joined via a glycosidic bond between two anomeric carbons • The product has two acetal groups and no hemiacetals • There are no reducing ends, this is a nonreducing sugar • Trehalose is a constituent of hemolymph of insects • Two common disaccharides.
    [Show full text]
  • Chem331 Lect 12 Carbos
    Carbohydrates • Of the macromolecules that we will cover in this class, those involving carbohydrates are the most abundant in nature. • Via photosynthesis, over 100 billion metric tons of CO2 and H2O are converted into cellulose and other plant products. • The term carbohydrate is a generic one that refers primarily to carbon-containing compounds that contain hydroxyl, keto, or aldehydic functionalities. • Carbohydrates can range in sizes, from simple monosaccharides (sugars) to oligosaccharides, to polysaccharides. What Roles Do Carbohydrates Play In Vivo? Energy—Photosynthesis, (CO2+ lightàSugar + O2) Structure—cell walls and extracellular structures in plants, animals and bacteria Conjugation onto lipids, proteins—glycosylation – Molecular Recognition – Protein Folding – Solubility DNA – DNA backbone – DNA capping Carbohydrate Naming Monosaccharides—simple sugars, can’t be broken down, molecular formula (CH2O)n Oligosaccharides—a few (2-10) monosaccharides linked together (conventional names: disaccharide, etc.) Polysaccharides—polymers of simple sugars. Can have molecular weights >1x106 g/mol Monosaccharide Structure and Naming The simplest aldose and ketose are both trioses—containing 3 carbon atoms HEXOSES are the most abundant sugar in nature (think: glucose) Stereochemistry Aldoses >3 carbons and Ketoses > 4 carbons all have chiral centers. Nomenclature for sugars specifies chirality—compared to glyceraldehyde: Aldose and Ketose Tree – see your book for figure Enantiomers and Diastereomers Diastereomers have opposite conformations
    [Show full text]
  • Metabolism of Lactic Acid Bacteria in Wheat Sourdough and Bread Quality
    University of Alberta Metabolism of Lactic Acid Bacteria in Wheat Sourdough and Bread Quality by Chonggang Zhang A thesis submitted to the Faculty of Graduate Studies and Research in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Food Science and Technology Agricultural, Food and Nutritional Science ©Chonggang Zhang Fall 2011 Edmonton, Alberta Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission. Dedication I would like to dedicate this thesis to my mother and my wife. Thanks for always supporting me during the hard time. Without you I couldn’t have gone so far. Abstract Study on metabolism of lactic acid bacteria in wheat sourdough can improve bread quality such as bread flavour, texture and shelf life. This dissertation focused on several metabolic pathways in Lactobacillus strains on both biochemical and genetic level to fulfill three objectives. The first objective was to produce bread preservative propionate from lactate by cometabolism of Lactobacillus buchneri and Lactobacillus diolivorans to extend bread shelf life.
    [Show full text]
  • Tarteel Sabrah Dr.Ma'moun Ahram
    7 Faculty of medicine – JU2018 Tarteel Sabrah Tarteel Sabrah Tarteel Sabrah Dr.Ma'moun Ahram Raffinose We talked about monosaccharide, we talked about disaccharide let's get big now . we will talk about oligosaccharide which is basically carbohydrates made of 3 to 10 monosaccharides or sugar residues Raffinose is an example . Raffinose is a trisaccharide that is made of three monosaccharides ( sugar residues) . If you look at structure first one is galactose then glucose and then fructose . from left to right It is Found in beans and vegetables like cabbage, Brussels, sprouts, broccoli, asparagus . And we can't digest raffinose because of Humans lack the Alpha-galactosidase enzyme that is needed to break down raffinose, but intestinal bacteria can ferment it into hydrogen, methane, and other gases but It is not as bad as lactose intolerance. Look at these monosaccharides and how are connected to each other as a practice whenever you see something like this look at each residue and try to identify it is it glucose, galactose and so on identify the anomeric configuration identify the glycosidic linkage between these different subunits Type of glycosidic bond between galactose and glucose [α: 16 ] Type of glycosidic bond between glucose and fructose [β: 12] 1 | P a g e We have oligosaccharide that can be larger and oligosaccharide that can be modified in certain ways so we can use them as antibiotics Oligosaccharides as drugs Streptomycin and erythromycin anticancer agents Doxorubicin Digoxin cardiovascular drug. STRUCTURES NOT
    [Show full text]
  • Resolution of Galactose, Glucose, Xylose and Mannose in Sugarcane
    *Manuscript Resolution of galactose, glucose, xylose and mannose in sugarcane bagasse employing a voltammetric electronic tongue formed by metals oxy- hydroxide/MWCNT modified electrodes Acelino Cardoso de Sá*1,2, Andrea Cipri2, Andreu González-Calabuig2, Nelson Ramos Stradiotto1 and Manel del Valle*,2 1Department of Analytical Chemistry, Institute of Chemistry, Universidade Estadual Paulista (UNESP), 55 Rua Francisco Degni, Araraquara 14800-060, SP, Brazil. 2Sensors and Biosensors Group, Department of Chemistry, Universitat Autònoma de Barcelona, Edifici Cn, 08193 Bellaterra, Barcelona, Spain *e-mail: [email protected] ABSTRACT Second generation ethanol is produced from the carbohydrates released from the cell wall of bagasse and straw of sugarcane. The objective of this work is the characterization and application of a voltammetric electronic tongue using an array of glassy carbon electrodes modified with multi-walled carbon nanotubes containing metal (Paladium, Gold, Copper, Nickel and Cobalt,) oxy-hydroxide nanoparticles (GCE/MWCNT/MetalsOOH) towards a simpler analysis of carbohydrates (glucose, xylose, galactose and mannose). The Artificial Neural Network (ANN) based prediction model has resulted satisfactory for all carbohydrates and the obtained response had shown an adequate accuracy. In this manner 192 architectures were evaluated. The final architecture of the back-propagation ANN model had 36 input neurons, a hidden layer with 5 neurons and the tansig transfer function, an output layer with 4 neurons and the purelin transfer function. All species a comparison correlation coefficient of r ≥ 0.99 for the training subset and of r ≥ 0.96 for the test subset, being close to the ideal value. Keywords: Electronic Tongue, Carbohydrates, Artificial Neural Network, Multi-walled carbon nanotubes, Metal nanoparticles, Second generation ethanol.
    [Show full text]
  • Pulp and Paper Chemistry and Technology Volume 1
    Pulp and Paper Chemistry and Technology Volume 1 Wood Chemistry and Wood Biotechnology Edited by Monica Ek, Göran Gellerstedt, Gunnar Henriksson Pulp and Paper Chemistry and Technology Volume 1 This project was supported by a generous grant by the Ljungberg Foundation (Stiftelsen Erik Johan Ljungbergs Utbildningsfond) and originally published by the KTH Royal Institute of Technology as the “Ljungberg Textbook”. Wood Chemistry and Biotechnology Edited by Monica Ek, Göran Gellerstedt, Gunnar Henriksson Editors Dr. Monica Ek Professor (em.) Dr. Göran Gellerstedt Professor Dr. Gunnar Henriksson Wood Chemistry and Pulp Technology Fibre and Polymer Technology School of Chemical Science and Engineering KTH Ϫ Royal Institute of Technology 100 44 Stockholm Sweden ISBN 978-3-11-021339-3 Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available in the Internet at http://dnb.d-nb.de. ” Copyright 2009 by Walter de Gruyter GmbH & Co. KG, 10785 Berlin. All rights reserved, including those of translation into foreign languages. No part of this book may be reproduced or transmitted in any form or by any means, electronic or mechanic, including photocopy, recording, or any information storage retrieval system, without permission in writing from the publisher. Printed in Germany. Typesetting: WGV Verlagsdienstleistungen GmbH, Weinheim, Germany. Printing and binding: Hubert & Co. GmbH & Co. KG, Göttingen, Germany. Cover design: Martin Zech, Bremen, Germany. Foreword The production of pulp and paper is of major importance in Sweden and the forestry industry has a profound influence on the economy of the country. The technical development of the industry and its ability to compete globally is closely connected with the combination of high-class education, research and development that has taken place at universities, institutes and industry over many years.
    [Show full text]
  • Polysaccharides
    Block 2 Carbohydrates ......................................................................................................................................................................................... UNIT 7 POLYSACCHARIDES Structure 7.1 Introduction 7.5 Glycoconjugates Proteoglycans Expected Learning Outcomes Glycoproteins 7.2 Classification of Polysaccharides Glycolipids and 7.3 Storage Polysaccharides Lipopolysaccharides Starch 7.6 Summary Glycogen 7.7 Terminal Questions 7.4 Structural Polysaccharides 7.8 Answers Cellulose 7.9 Further Readings Chitin Glycosaminoglycans 7.1 INTRODUCTION In the previous units, we discussed about structures and properties of monosaccharides and oligosaccharides. We also learnt how nature of the glycosidic bonds affects the properties of the oligosaccharides and their digestion by enzymes in human body. In this unit, we shall discuss about polysaccharides. Most of the carbohydrates in nature are polysaccharides. Some of them are simply polymers of monosaccharides like starch, glycogen and cellulose while others in addition to being polymeric saccharides are also linked covalently to other biomolecules like amino acids, peptides, proteins and lipids. These show not only structural diversity but also perform diverse functions. Let us now look at these aspects by studying different examples of polysaccharides. Objectives After going through this unit, you should be able to: v classify polysaccharides; v draw structures of energy storing forms of sugars; starch, glycogen, and discuss their properties;
    [Show full text]
  • Full Text in DIVA
    Aspects of optimizing pulp fibre properties for tissue and packaging materials Hafizur Rahman Main supervisor: Prof. Armando Cordova Co-supervisors: Prof. Per Engstrand Asst. Prof. Börje Norlin Faculty of Science, Technology and Media Thesis for Doctoral degree in Chemical Engineering Mid Sweden University Sundsvall, 2021-06-14 Akademisk avhandling som med tillstånd av Mittuniversitetet i Sundsvall framläggs till offentlig granskning för avläggande av teknologie doktorsexamen i kemiteknik, Måndagen den 14:e juni, 2021 klockan 10:00 i sal C312 , Mittuniversitetet Sundsvall. Seminariet kommer att hållas på engelska. Aspects of optimizing pulp fibre properties for tissue and packaging materials © Hafizur Rahman, 2021-06-14 Printed by Mid Sweden University, Sundsvall, Sweden ISSN: 1652-893X ISBN: 978-91-89341-15-9 Faculty of Science, Technology and Media Mid Sweden University, SE-851 70 Sundsvall, Sweden Phone: +46 (0)10 142 80 00 Mid Sweden University Doctoral Thesis 348 iii iv Table of contents ABSTRACT ....................................................................................................... viii SAMMANFATTNING .......................................................................................... ix LIST OF PAPERS ................................................................................................ x CONTRIBUTION TO THE PAPERS .................................................................... xi LIST OF RELATED PAPERS AND PUBLICATIONS ........................................ xii CONFERENCES AND SEMINARS ..................................................................
    [Show full text]