DOCSLIB.ORG

An Introduction to Polysaccharide Biotechnology, Second Edition

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
An Introduction to Polysaccharide Biotechnology, Second Edition BIOCHEMISTRY BIOTECHNOLOGY AN INTRODUCTION TO POLYSACCHARIDE Stephen E. Harding • Michael P. Tombs An Introduction to Gary G. Adams • Berit Smestad Paulsen POLYSACCHARIDE Kari Tvete Inngjerdingen • Hilde Barsett BIOTECHNOLOGY An Introduction to SECOND EDITION Polysaccharides and related high molecular weight glycans are hugely diverse with wide application in biotechnology and great opportunities for further exploitation. POLYSACCHARIDE An Introduction to Polysaccharide Biotechnology – a second edition of the popular original text by Tombs and Harding – introduces students, researchers, clinicians and industrialists to the properties of some of the key materials involved, how these are applied, some of the economic factors concerning their production and how they BIOTECHNOLOGY are characterised for regulatory purposes. FEATURES • Basic properties of polysaccharides and how they are very different to proteins SECOND EDITION • How these properties are affected by enzymes and how the effects of enzymes can be controlled • An introduction to some ‘patent preferred’ methodologies for polysaccharide EDITION SECOND characterisation, such as molecular weight distribution • Applications in biopharma, food and other industries • The application of marker-assisted selection to fruit ripening and preservation, the development of glycovaccines against meningitis and other serious diseases • Barsett Paulsen • Inngjerdingen • Adams Harding • Tombs • A whole chapter dedicated to a case study on bioactivity and how modern research is unlocking the way polysaccharides are at the core of many HG HG traditional medicines • Further Reading sections for follow up K23616 6000 Broken Sound Parkway, NW Suite 300, Boca Raton, FL 33487 RG-I RG-II 711 Third Avenue New York, NY 10017 2 Park Square, Milton Park Abingdon, Oxon OX14 4RN, UK www.crcpress.com An Introduction to Polysaccharide Biotechnology An Introduction to Polysaccharide Biotechnology By Stephen E. Harding, Michael P. Tombs and Gary G. Adams University of Nottingham, UK and Berit Smestad Paulsen, Kari Tvete Inngjerdingen and Hilde Barsett University of Oslo, Norway 2nd Edition CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2017 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed on acid-free paper International Standard Book Number-978-1-4822-4697-1 (Hardback) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, 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, and recording, 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 www.copyright.com (http:// www.copyright.com/) 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 registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data Names: Harding, S. E. (Stephen E.) Title: An Introduction to Polysaccharide Biotechnology. Description: Second edition / Stephen E. Harding [and five others]. | Boca Raton : CRC Press, [2017] | Includes bibliographical references and index. Identifiers: LCCN 2016040404 | ISBN 9781482246971 (hbk : alk. paper) | ISBN 9781315372730 (ebk : alk. paper) Subjects: LCSH: Polysaccharides--Biotechnology. | Polysaccharides--Metabolism. | Glucosidases--Biotechnology. Classification: LCC TP248.65.P64 T66 2017 | DDC 660.6/3--dc23 LC record available at https://lccn.loc.gov/2016040404 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Preface to First Edition ............................................................................................................................................................................ xi Preface to Second Edition ..................................................................................................................................................................xiii Chapter 1 Polysaccharides and Their Potential for Biotechnology ....................................................................... 1 1.1 An Introduction to Polysaccharides .................................................................................................. 1 1.1.1 Glycosubstances and Glycans ........................................................................................... 2 1.1.2 Structures, Nomenclature and Abbreviations ......................................................... 3 1.1.3 Polysaccharide Polydispersity: Molecular Weight Averages ........................... 9 1.1.4 Solution Properties and Characterization Methods ..........................................10 1.1.5 Measurement of Molecular Weight Averages and Molecular Weight Distribution ...............................................................................................................10 1.1.6 Polysaccharide Conformation in Solution ...............................................................16 1.1.6.1 Overall or ‘Gross’ Conformation: Haug Triangle .............................16 1.1.6.2 Effect of Ionic Strength of the Surrounding Medium ................18 1.1.6.3 Intrinsic Viscosity ...............................................................................................18 1.1.6.4 Conformation Zones.......................................................................................19 1.1.6.5 More Specific Conformation Information: Rigid Structures ..................................................................................................20 1.1.6.6 Flexible Structures: Worm-Like Coil and Persistence Length ...........................................................................................21 1.1.6.7 Ordered Structure ............................................................................................21 1.1.7 Imaging of Polysaccharides: X-Ray Fibre Diffraction, Electron Microscopy and Atomic Force Microscopy .............................................................21 1.1.8 Polysaccharide Rheology ...................................................................................................23 1.1.9 Classification of Polysaccharides ....................................................................................25 1.1.10 The Cell Wall ...............................................................................................................................26 1.1.10.1 Cellulose .................................................................................................................26 1.1.10.2 Mannans .................................................................................................................26 1.1.10.3 Callose .....................................................................................................................26 1.1.10.4 Heteropolymers .................................................................................................26 1.1.10.5 Heteroglucans ....................................................................................................27 1.1.10.6 Heteroxylans ........................................................................................................27 1.1.10.7 Galactomannans, Glucomannans and Galactoglucomannans ..................................................................................27 1.1.10.8 Pectins .....................................................................................................................27 1.1.10.9 Glycoproteins or Extensins ..........................................................................28 1.1.10.10 Lignins .....................................................................................................................28 1.1.10.11 Alginates .................................................................................................................28 1.1.10.12 Carrageenans ......................................................................................................28 1.1.10.13 Furcellaran .............................................................................................................29 1.1.10.14 Fucans ......................................................................................................................29 1.1.10.15 Other Components
Load more

Recommended publications
  • Structure of an Acidic Polysaccharide Elaborated by Acetobacter Sp
    Agric. Biol. Chem., 50 (5), 1271 ~1278, 1986 1271 Structure of an Acidic Polysaccharide Elaborated by Acetobacter sp. NBI 10051" Kenji Tayama, Hiroyuki Minakami, Seiichi Fujiyama, Hiroshi Masai and Akira Misaki* NakanoBiochemical Research Institute, NakanoVinegar Co., Ltd., Handa, Aichi 475, Japan * Faculty of Science of Living, Osaka City University, Sugimoto-cho, Sumiyoshi, Osaka 558, Japan Received November 19, 1985 An extracellular acidic polysaccharide elaborated by Acetobacter sp. NBI1005 was composed of D-glucose, D-galactose, D-mannose, and D-glucuronic acid (approximate molar ratio, 6 : 2 : 1 : 1). Methylation and fragmentation analysis by partial acid hydrolysis indicated that the polysaccharide has a branched structure containing a backbone chain of /?-(l ->4)-linked D-glucose residues, two out of every four glucose residues being substituted at the 0-3 positions to form two kinds of branches, one consisting of D-mannose and D-glucuronic acid residues and the other of (l ->6)-linked D-galactose and D-glucose residues. Some microorganisms belonging to Ace- cosyl-(l ->4)-D-glucuronosyl-(l ->2)-D-man- tobacter species have been knownto produce nose.9) This paper reports the structural fea- extracellular polysaccharides, such as cellu- ture of polysaccharide AM-1, as revealed by lose,1* dextran,2) levan,3) and an acidic poly- methylation, fragmentation analysis, and en- saccharide,4* and also soluble, /?-(l-»2)- zymatic degradation. branched, £-(1 ^4)-D-glucan5) and )8-(l -»2)- D-glucan.6) In the course of study on acetic MATERIALS AND METHODS acid bacteria (genera Acetobacter and Glu- conobacter) having a high productivity of Materials. Polysaccharide AM-1of Acetobacter sp.
    [Show full text]
  • Download Author Version (PDF)
    Environmental Science: Nano CdS Nanoparticles in Soil Induce Metabolic Reprogramming in Broad Bean (Vicia faba L.) Roots and Leaves Journal: Environmental Science: Nano Manuscript ID EN-ART-08-2019-000933.R1 Article Type: Paper Page 1 of 36 Environmental Science: Nano 1 2 3 4 The rapid development of nanotechnology has raised concern regarding the 5 6 7 environmental toxicity of nanoparticles (NPs). However, little is known about the 8 9 molecular mechanisms underlying NP toxicity in plants. Understanding toxic 10 11 12 mechanisms in organisms at molecular level, especially in crop plants, is important for 13 14 their sustainable use and development. In this study, although none of the phenotypic 15 16 17 parameters of broad bean plants (photosynthetic pigments contents, biomass, and lipid 18 19 20 peroxidation) were overtly impacted in response to CdS-NPs in soil during 28 d of 21 22 exposure, metabolomics revealed marked and statistically significant alterations in the 23 24 25 metabolite profiles of plant roots and leaves. The reprogramming of antioxidant 26 27 metabolite production presumably reflected the molecular defense response of the 28 29 30 plants to CdS-NPs stress. The sensitive responses of flavone, putrescine and 31 32 33 noradrenaline in the leaves suggests the use of these compounds in legumes as 34 35 biomarkers of oxidative stress induced by the presence of CdS-NPs in soil. 36 37 38 Metabolomics might thus be a suitable approach for the early detection of soil 39 40 contamination by Cd. In the plants, the reprogramming of carbon and nitrogen 41 42 43 metabolism (including sugars, organic acids, amino acids, and N-containing 44 45 46 compounds) alleviated the toxicity of CdS-NPs, which may have been caused by free 47 48 Cd2+ ions or perhaps by a particle-specific response.
    [Show full text]
  • Electronic Supplementary Information
    Electronic Supplementary Material (ESI) for Chemical Science. This journal is © The Royal Society of Chemistry 2019 Electronic Supplementary Information Poly(ionic liquid)s as a Distinct Receptor Material to Create Highly- Integrated Sensing Platform for Efficiently Identifying a Myriad of Saccharides Wanlin Zhang, Yao Li, Yun Liang, Ning Gao, Chengcheng Liu, Shiqiang Wang, Xianpeng Yin, and Guangtao Li* *Corresponding authors: Guangtao Li ([email protected]) S1 Contents 1. Experimental Section (Page S4-S6) Materials and Characterization (Page S4) Experimental Details (Page S4-S6) 2. Figures and Tables (Page S7-S40) Fig. S1 SEM image of silica colloidal crystal spheres and PIL inverse opal spheres. (Page S7) Fig. S2 Adsorption isotherm of PIL inverse opal. (Page S7) Fig. S3 Dynamic mechanical analysis and thermal gravimetric analysis of PIL materials. (Page S7) Fig. S4 Chemical structures of 23 saccharides. (Page S8) Fig. S5 The counteranion exchange of PIL photonic spheres from Br- to DCA. (Page S9) Fig. S6 Reflection and emission spectra of spheres for saccharides. (Page S9) Table S1 The jack-knifed classification on single-sphere array for 23 saccharides. (Page S10) Fig. S7 Lower detection concentration at 10 mM of the single-sphere array. (Page S11) Fig. S8 Lower detection concentration at 1 mM of the single-sphere array. (Page S12) Fig. S9 PIL sphere exhibiting great pH robustness within the biological pH range. (Page S12) Fig. S10 Exploring the tolerance of PIL spheres to different conditions. (Page S13) Fig. S11 Exploring the reusability of PIL spheres. (Page S14) Fig. S12 Responses of spheres to sugar alcohols. (Page S15) Fig.
    [Show full text]
  • BASICS of the FODMAP DIET Elizabeth English RD, CLC OBJECTIVES
    BASICS OF THE FODMAP DIET Elizabeth English RD, CLC OBJECTIVES Describe sources of FODMAP carbohydrate Recognize appropriate patient populations for the FODMAP diet Identify high FODMAP foods which are necessary to restrict when following the FODMAP diet Identify low FODMAP foods which are allowed when following the FODMAP diet FODMAP • Fermentable • Oligosaccharides • Disaccharides • Monosaccharides • And • Polyols POPULATION • Prevalence of IBS varies between 8% - 20% of the US population depending on diagnostic criteria and population evaluated • Most studies report a higher prevalence of IBS in women than men • Average medical expenditure for IBS in the US is estimated to be $1.35 billion in direct costs and $205 million in indirect costs • IBS accounts for almost half of all visits to gastroenterologists MAGGE & LEMBO . GASTORENTEROLOGY & HEPATOLOGY 2012 KIDS • Kids with FGID (functional gastrointestinal disorders) report lower quality of life than healthy controls •Increased incidence of school absenteeism •Decreased energy •Less likely to be physically active •Less likely to be involved in school activities •Increased feelings of sadness and loneliness YOUSSEF ET AL. PEDIATRICS 2014 TARGET POPULATION • Patients diagnosed with functional gastrointestinal diseases (FGIDs) including IBS, abdominal migrane & childhood functional abdominal pain • Diagnosis by exclusion • Celiac disease • IBD • Food allergies • EoE • Cancer • Gastritis FODMAP HISTORY • Sue Shepherd developed the FODMAP diet in 1999 at her Shepherd Works RD practice • Realized that FODMAP foods were triggers for IBS • In 2005, the first paper describing FODMAPs was published with Dr. Peter Gibson • In 2006, the first research trial was a retrospective audit of patients with IBS and fructose malabsorption on a low fructose/fructan diet with 74% of patients reporting symptomatic improvement on this dietary regimen • Early research continued until 2009 when the FODMAP diet became well known throughout the digestive community BARRETT & GIBSON.
    [Show full text]
  • Sugars and Plant Innate Immunity
    Journal of Experimental Botany Advance Access published May 2, 2012 Journal of Experimental Botany, Page 1 of 10 doi:10.1093/jxb/ers129 REVIEW PAPER Sugars and plant innate immunity Mohammad Reza Bolouri Moghaddam and Wim Van den Ende* KU Leuven, Laboratory of Molecular Plant Biology, Kasteelpark Arenberg 31, B-3001 Leuven, Belgium * To whom correspondence should be addressed. E-mail: [email protected] Received 27 January 2012; Revised 25 March 2012; Accepted 30 March 2012 Abstract Sugars are involved in many metabolic and signalling pathways in plants. Sugar signals may also contribute to Downloaded from immune responses against pathogens and probably function as priming molecules leading to pathogen-associated molecular patterns (PAMP)-triggered immunity and effector-triggered immunity in plants. These putative roles also depend greatly on coordinated relationships with hormones and the light status in an intricate network. Although evidence in favour of sugar-mediated plant immunity is accumulating, more in-depth fundamental research is required to unravel the sugar signalling pathways involved. This might pave the way for the use of biodegradable http://jxb.oxfordjournals.org/ sugar-(like) compounds to counteract plant diseases as cheaper and safer alternatives for toxic agrochemicals. Key words: immunity, pathogen, priming, signal, sugar. Introduction by guest on March 24, 2016 Sugars such as glucose, fructose, and sucrose are recognized Chisholm et al., 2006). Sugars are well known to activate as signalling molecules in plants (Rolland et al., 2006; various pattern recognition genes (Herbers et al., 1996a,b; Bolouri-Moghaddam et al., 2010), in addition to their Johnson and Ryan, 1990).
    [Show full text]
  • Improving the Utilization of Isomaltose and Panose by Lager Yeast Saccharomyces Pastorianus
    fermentation Article Improving the Utilization of Isomaltose and Panose by Lager Yeast Saccharomyces pastorianus Javier Porcayo Loza 1,2,† , Anna Chailyan 3, Jochen Forster 3 , Michael Katz 3, Uffe Hasbro Mortensen 2,* and Rosa Garcia Sanchez 3,* 1 Novo Nordisk Foundation Center for Biosustainability, Technical University of Denmark, 2800 Kongens Lyngby, Denmark; [email protected] 2 Department of Bioengineering, Technical University of Denmark, 2800 Kongens Lyngby, Denmark 3 Carlsberg A/S, Carlsberg Research Laboratory, 1799 Copenhagen V, Denmark; [email protected] (A.C.); [email protected] (J.F.); [email protected] (M.K.) * Correspondence: [email protected] (U.H.M.); [email protected] (R.G.S.) † Current address: Graphenea S.A., 20009 San Sebastian, Spain. Abstract: Approximately 25% of all carbohydrates in industrial worts are poorly, if at all, fermented by brewing yeast. This includes dextrins, β-glucans, arabinose, xylose, disaccharides such as isomaltose, nigerose, kojibiose, and trisaccharides such as panose and isopanose. As the efficient utilization of carbohydrates during the wort’s fermentation impacts the alcohol yield and the organoleptic traits of the product, developing brewing strains with enhanced abilities to ferment subsets of these sugars is highly desirable. In this study, we developed Saccharomyces pastorianus laboratory yeast strains with a superior capacity to grow on isomaltose and panose. First, we designed a plasmid toolbox for Citation: Porcayo Loza, J.; Chailyan, the stable integration of genes into lager strains. Next, we used the toolbox to elevate the levels of A.; Forster, J.; Katz, M.; Mortensen, the α-glucoside transporter Agt1 and the major isomaltase Ima1.
    [Show full text]
  • Sweetness and Sensory Properties of Commercial and Novel Oligosaccharides Of
    1 Sweetness and sensory properties of commercial and novel oligosaccharides of 2 prebiotic potential 3 4 Laura Ruiz-Aceitunoa, Oswaldo Hernandez-Hernandeza, Sofia Kolidab, F. Javier 5 Morenoa,* and Lisa Methvenc 6 7 a Institute of Food Science Research, CIAL (CSIC-UAM), Nicolás Cabrera 9, 28049 8 Madrid (Spain) 9 b OptiBiotix Health plc, Innovation Centre, Innovation Way, Heslington, York YO10 10 5DG (UK) 11 c Sensory Science Centre, Department of Food and Nutritional Sciences, The University 12 of Reading, PO Box 226, Whiteknights, Reading RG6 6AP (UK) 13 14 *Corresponding author: [email protected] Tel (+34) 91 0017948 1 15 Abstract 16 This study investigates the sweetness properties and other sensory attributes of ten 17 commercial and four novel prebiotics (4-galactosyl-kojibiose, lactulosucrose, lactosyl- 18 oligofructosides and raffinosyl-oligofructosides) of high degree of purity and assesses the 19 influence of their chemical structure features on sweetness. The impact of the type of 20 glycosidic linkage by testing four sucrose isomers, as well as the monomer composition 21 and degree of polymerization on sweetness properties were determined. Data from the 22 sensory panel combined with principal component analysis (PCA) concludes that chain 23 length was the most relevant factor in determining the sweetness potential of a 24 carbohydrate. Thus, disaccharides had higher sweetness values than trisaccharides which, 25 in turn, exhibited superior sweetness than mixtures of oligosaccharides having DP above 26 3. Furthermore, a weak non-significant trend indicated that the presence of a ketose sugar 27 moiety led to higher sweetness. The novel prebiotics tested in this study had between 18 28 and 25% of relative sweetness, in line with other commercial prebiotics, and samples 29 varied in their extent of off flavour.
    [Show full text]
  • Enzymatic Synthesis of Α-Glucosides Using Various Enzymes
    Chapter 1 Reviews: Enzymatic Synthesis of α-Glucosides Using Various Enzymes 1.1 Introduction In recent years, transglycosylation or reverse hydrolysis reactions catalyzed by glycosidases have been applied to in vitro synthesis of oligosaccharides1-8) and alkylglycosides7-14). Glucosylation is considered to be one of the important methods for the structural modification of compounds having -OH groups with useful biological activities since it increases water solubility and improves pharmacological properties of the original compounds. Enzymatic synthesis is superior to the chemical synthesis methods in such cases that the enzymatic reactions proceed regioselectively and stereoselectively without protection and deprotection processes. In addition, the enzymatic reactions occur usually under mild conditions: at ordinary temperature and pressure, and a pH value around neutrality. Various compounds, such as drugs13, 17), vitamins and their analogues15, 16), and phenolic compounds17), have been anomer-selectively glucosylated by microbial glycosidases. In this chapter, the methods for enzymatic synthesis of several glucosides and mechanism of xanthan gum synthesis by Xanthomonas campestris are reviewed in details. 1 1.2 Enzymatic synthesis of glucosides 1.2.1 Neohesperidin α-glucoside synthesis using cyclodextrin glucanotransferase of Bacillus sp. A2-5a18) Citrus fruits contain two groups of flavonoid glycosides that have either rutinose (L-rhaminopyranosyl-α-1, 6-glucopyranoside) or neohesperidose (L- rhaminopyranosyl-α-1, 2-glucopyranoside) as their saccharide components. Hesperidin from mandarin oranges is tasteless. Neohesperidin from grapefruits is intensely bitter and important in citrus juices since it is converted into sweet dihydrochalcone derivatives by hydrogenation. However, since their solubilities in water are very low, enzymatic modification of neohesperidin was expected for applications in the food industry.
    [Show full text]
  • Congenital Sucrase-Isomaltase Deficiency
    Congenital sucrase-isomaltase deficiency Description Congenital sucrase-isomaltase deficiency is a disorder that affects a person's ability to digest certain sugars. People with this condition cannot break down the sugars sucrose and maltose. Sucrose (a sugar found in fruits, and also known as table sugar) and maltose (the sugar found in grains) are called disaccharides because they are made of two simple sugars. Disaccharides are broken down into simple sugars during digestion. Sucrose is broken down into glucose and another simple sugar called fructose, and maltose is broken down into two glucose molecules. People with congenital sucrase- isomaltase deficiency cannot break down the sugars sucrose and maltose, and other compounds made from these sugar molecules (carbohydrates). Congenital sucrase-isomaltase deficiency usually becomes apparent after an infant is weaned and starts to consume fruits, juices, and grains. After ingestion of sucrose or maltose, an affected child will typically experience stomach cramps, bloating, excess gas production, and diarrhea. These digestive problems can lead to failure to gain weight and grow at the expected rate (failure to thrive) and malnutrition. Most affected children are better able to tolerate sucrose and maltose as they get older. Frequency The prevalence of congenital sucrase-isomaltase deficiency is estimated to be 1 in 5, 000 people of European descent. This condition is much more prevalent in the native populations of Greenland, Alaska, and Canada, where as many as 1 in 20 people may be affected. Causes Mutations in the SI gene cause congenital sucrase-isomaltase deficiency. The SI gene provides instructions for producing the enzyme sucrase-isomaltase.
    [Show full text]
  • Rational Design of an Improved Transglucosylase for Production of the Rare Sugar Nigerose† Cite This: Chem
    ChemComm COMMUNICATION Rational design of an improved transglucosylase for production of the rare sugar nigerose† Cite this: Chem. Commun., 2019, 55,4531 Jorick Franceus,a Shari Dhaene,a Hannes Decadt,a Judith Vandepitte,a Received 25th February 2019, Jurgen Caroen,b Johan Van der Eycken,b Koen Beerensa and Tom Desmet *a Accepted 26th March 2019 DOI: 10.1039/c9cc01587f rsc.li/chemcomm The sucrose phosphorylase from Bifidobacterium adolescentis (BaSP) can be used as a transglucosylase for the production of rare sugars. We designed variants of BaSP for the efficient synthesis of nigerose from sucrose and glucose, thereby adding to the inventory of rare sugars that can conveniently be produced from bulk sugars. Rare sugars hold tremendous potential for practical applications in various industries.1 Regardless, few of them have been exploited Fig. 1 Transglucosylation of glucose by mutant Q345F of the B. adoles- centis sucrose phosphorylase, resulting in the synthesis of maltose and commercially due to their scarcity in nature which prevents nigerose. them from being isolated in large quantities. These compounds have consequently become attractive targets for biocatalytic production processes starting from affordable and widely avail- kojibiose, but instead produces an equimolar mixture of maltose able carbohydrates.2 and nigerose (Fig. 1).9–12 The sucrose phosphorylase from Bifidobacterium adolescentis Nigerose is the rare a-(1,3)-bonded disaccharide of glucose that (BaSP; carbohydrate-active enzyme database family GH13) is a occurs in nature as a constituent of polysaccharides such as nigeran. particularly interesting candidate enzyme for the production of It is also found in Japanese rice wine or sake, hence its alternative such rare sugars.
    [Show full text]
  • Structural Features
    1 Structural features As defined by the International Union of Pure and Applied Chemistry gly- cans are structures of multiple monosaccharides linked through glycosidic bonds. The terms sugar and saccharide are synonyms, depending on your preference for Arabic (“sukkar”) or Greek (“sakkēaron”). Saccharide is the root for monosaccha- rides (a single carbohydrate unit), oligosaccharides (3 to 20 units) and polysac- charides (large polymers of more than 20 units). Carbohydrates follow the basic formula (CH2O)N>2. Glycolaldehyde (CH2O)2 would be the simplest member of the family if molecules of two C-atoms were not excluded from the biochemical repertoire. Glycolaldehyde has been found in space in cosmic dust surrounding star-forming regions of the Milky Way galaxy. Glycolaldehyde is a precursor of several organic molecules. For example, reaction of glycolaldehyde with propenal, another interstellar molecule, yields ribose, a carbohydrate that is also the backbone of nucleic acids. Figure 1 – The Rho Ophiuchi star-forming region is shown in infrared light as captured by NASA’s Wide-field Infrared Explorer. Glycolaldehyde was identified in the gas surrounding the star-forming region IRAS 16293-2422, which is is the red object in the centre of the marked square. This star-forming region is 26’000 light-years away from Earth. Glycolaldehyde can react with propenal to form ribose. Image source: www.eso.org/public/images/eso1234a/ Beginning the count at three carbon atoms, glyceraldehyde and dihydroxy- acetone share the common chemical formula (CH2O)3 and represent the smallest carbohydrates. As their names imply, glyceraldehyde has an aldehyde group (at C1) and dihydoxyacetone a carbonyl group (at C2).
    [Show full text]
  • WO 2013/070444 Al 16 May 2013 (16.05.2013) W P O P C T
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2013/070444 Al 16 May 2013 (16.05.2013) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A23G 4/00 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/US20 12/062043 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 26 October 2012 (26.10.2012) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, (26) Publication Language: English RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (30) Priority Data: ZM, ZW. 61/556,546 7 November 20 11 (07. 11.201 1) US (84) Designated States (unless otherwise indicated, for every (71) Applicant (for all designated States except US): WVI. kind of regional protection available): ARIPO (BW, GH, WRIGLEY JR. COMPANY [US/US]; 1132 Blackhawk GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, Street, Chicago, IL 60642 (US).
    [Show full text]