Handbook of Polysaccharides
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Handbook of Polysaccharides Toolbox for Polymeric sugars Polysaccharide Review I 2 Global Reach witzerland - taad lovakia - Bratislava Synthetic laboratories Synthetic laboratories Large-scale manufacture Large-scale manufacture Distribution hub Distribution hub apan - Tokyo Sales office United Kingdom - Compton India - Chennai Synthetic laboratories Sales office United tates - an iego Distribution hub Distribution hub China - Beijing, inan, uzhou outh Korea - eoul Synthetic laboratories Sales office Large-scale manufacture Distribution hub Table of contents Section Page Section Page 1.0 Introduction 1 6.2 Examples of Secondary & Tertiary Polysaccharide Structures 26 About Biosynth Carbosynth 2 6.2.1 Cellulose 26 Product Portfolio 3 6.2.2 Carrageenan 27 Introduction 4 6.2.3 Alginate 27 2.0 Classification 5 6.2.4 Xanthan Gum 28 3.0 Properties and Applications 7 6.2.5 Pectin 28 4.0 Polysaccharide Isolation and Purification 11 6.2.6 Konjac Glucomannan 28 4.1 Isolation Techniques 12 7.0 Binary & Ternary Interactions Between Polysaccharides 29 4.2 Purification Techniques 12 7.1 Binary Interactions 30 5.0 Polysaccharide Structure Determination 13 7.2 Ternary Interactions 30 5.1 Covalent Primary Structure 13 8.0 Polysaccharide Review 31 5.1.1 Basic Structural Components 13 Introduction 32 5.1.2 Monomeric Structural Units and Substituents 13 8.1 Polysaccharides from Higher Plants 32 5.2 Linkage Positions, Branching & Anomeric Configuration 15 8.1.1 Energy Storage Polysaccharides 32 5.2.1 Methylation Analysis 16 8.1.2 Structural Polysaccharides 33 5.2.2 Retro Analysis by Partial Degradation 17 8.1.3 Polysaccharides from Seeds & Legumes 39 5.2.3 Spectroscopic Methods of Analysis 17 8.1.4 Exudate Gums 41 5.3 Molecular Weight Determination 19 8.1.5 Polysaccharides from Tubers 43 5.3.1 Light Scattering 19 8.2 Polysaccharides from Lichens 44 5.3.2 Size Exclusion Chromatography 20 8.2.1 Lichenan and Isolichenan 44 5.3.3 Ultracentrifugation 20 8.2.2 Pustulan 45 5.3.4 Viscosity 20 8.3 Polysaccharides from Algae 45 5.4 Polysaccharide Physical Properties 21 8.3.1 Polysaccharides from Rhodophyceae (Red algae) 45 5.4.1 Rheology 21 8.3.2 Polysaccharides from Phaeophyceae (Brown algae) 48 5.4.2 Gelation 22 8.3.3 Polysaccharides from Chlorophyceae (Green algae) 49 5.4.3 Surface, Emulsification and Film-Forming Properties 23 8.4 Polysaccharides from Microorganisms 50 6.0 Secondary/Tertiary Structure and Function 25 8.4.1 Polysaccharides from Gram-negative Bacteria 50 6.1 Introduction 26 8.4.2 Polysaccharides from Gram-positive Bacteria 53 Section Page Section Page 8.5 Polysaccharides from Yeasts & Fungi 53 8.7.14 Carboxymethyl Dextran 68 8.5.1 Beta Glucans 53 8.7.15 Diethylaminoethyl Dextran 68 8.5.2 Mannan from Saccharomyces cerevisiae 54 8.7.16 Fluorescein Isothiocyanate Dextran 69 8.5.3 Curdlan 54 8.7.17 Carboxymethyl Curdlan 69 8.5.4 Pullulan 55 8.7.18 Propylene Glycol Alginate 69 8.5.5 Schizophyllan 55 8.8 Formulated Polysaccharides 70 8.5.6 Scleroglucan 56 8.8.1 Danaparoid 70 8.5.7 Glucuronoxylomannan from Cyptococcus neoformans 56 8.8.2 Polyglycoplex 70 8.5.8 Nigeran 56 8.9 Artificial Polysaccharides 70 8.6 Polysaccharides from Animal or Fish Tissues 57 8.9.1 Polydextrose 70 8.6.1 Energy Storage Polysaccharides 57 9.0 References 71 8.6.2 Structural Polysaccharides 58 Acknowledgements 79 8.6.3 Polysaccharides with Key Physiological Functions 60 8.7 Functionally Modified Polysaccharides 62 8.7.1 Methyl and Ethyl Cellulose 62 8.7.2 Hydroxypropyl Cellulose, Hydroxyethyl Cellulose and Ethyl Hydroxyethyl Cellulose 62 8.7.3 Hydroxypropyl Methyl Cellulose 63 8.7.4 Hydroxypropyl Methylcellulose Phthalate 64 8.7.5 Sodium Carboxymethyl Cellulose 64 8.7.6 Cellouronic Acid 65 8.7.7 Cellulose Acetete Hydrogen Phthalate 65 8.7.8 Cellulose Acetate 65 8.7.9 Carboxymethyl Chitosan 66 8.7.10 Glycol Chitosan 66 8.7.11 Hyaluronate Fluorescein 66 8.7.12 Dextran Biotin and Rhodamine 67 8.7.13 Dextran Sulphate 68 Section1 & 2 Introduction and Classification Introduction and Classification I 1 1 About Biosynth Carbosynth The Carbohydrate and Nucleoside Experts We pride ourselves in being the world-leading experts in the field of enzyme substrates, carbohydrate and nucleoside chemistry. Our mission is to expand the reach of our world-leading expertise in carbohydrates and nucleosides, and to provide it to innovators developing cutting-edge products that will improve the quality of life for millions of people worldwide. We are committed to continuous improvement and are working towards becoming the favourite resource for scientists developing revolutionary medicines and diagnostics. With sites on three continents, we have a global reach and serve customers around the globe. The two divisions Pharmaceutical & Diagnostic Products Division Research Products Division We are here to tailor products and services to your needs. We are here to support innovators with their cutting-edge research. We have extensive experience in serving customers on high- profile projects with rich internal know-how and process We are proud of opening the door to new discoveries by development skills across all our sites. We are proud of offering rare carbohydrates and nucleosides as well as being extremely successful in project work by providing newly characterised biochemical probes. Our products the solutions to a very high standard. support scientists working in organic chemistry, glycobiology, microbiology, immunology, cancer and neuroscience research. Our P&D team is composed of highly qualified professionals with extensive experience of working with pharmaceutical Our R&D team ensures that our diverse selection of research and diagnostics customers. products is of the highest quality and on the way to your lab. Services Ordering • Our offering of services include: You can conveniently order products online via our website www.biosynth-carbosynth.com Chemistry • Custom synthesis You can also place an order or make a product • Large-scale manufacturing enquiry via email at [email protected] • API manufacturing • Quality control and quality assurance For more information, please visit our website • CDMO services www.biosynth-carbosynth.com • Custom filling and packaging • Logistics and warehousing • Sourcing Biology 2 I About Biosynth Carbosynth 1 Product Portfolio Carbohydrates Fine Chemicals Nucleosides Enzyme Substrates Chemistry Reducing Agent Phospholipids Antimicrobials Natural Products Detergents Biology Product Portfolio I 3 1 Introduction Welcome to the Biosynth Carbosynth(R) toolbox and catalogue of polysaccharides and related biopolymers. These important products have a huge range of uses that exploit their unique functionalities across the food, pharmaceutical and industrial sectors. However, due to their complexity and diverse attributes, other laboratory suppliers have included them in general biochemical listings. In recognition of this, Biosynth Carbosynth(R) has assembled these products in a dedicated toolbox and catalogue to provide comprehensive support for your research, development and application requirements. Biosynth Carbosynth(R) has recently acquired the speciality polysaccharide business Glycomix and the combined strengths of products, applications, analysis and process development will provide you with a fully integrated range of products and services. This new toolbox and catalogue will guide you through the complexities of these important carbohydrates in some detail including sources, properties, applications and the relationship between their primary, secondary & tertiary structures and functionality. The most important analytical procedures for structural determination will also be discussed. As an additional tool to provide background detail, a review section has been included covering the product range. Each polysaccharide has been examined in some detail outlining the source, covalent structure, important functionalities and key references. Finally, the catalogue section contains the comprehensive range of polysaccharides that Biosynth Carbosynth(R) now offers for research and development. 4 I Introduction 2 Classification Polysaccharides have been recognized and exploited by man for centuries. As far as is known, they occur as energy reserves and structural materials in the tissues of all living things. In animals their structural role is performed in connective tissue, in plants in the cell walls, and in microorganisms as cell-wall materials and extracellular capsules. A large number of polysaccharides obtained from plants, animals and microorganisms including seeds, algae, fruits, plant cell walls, animal tissues, bacteria and fungi have been developed into commercially important products known collectively as industrial gums (Whistler, 1993) and, in Table 1, examples of these are listed and categorized according to source and type. In addition, a large number of carbohydrate polymers have been developed as reaction products of the natural polysaccharides listed in Table 1. Examples of these are the ethers, esters and sulphated derivatives of cellulose, starch, dextran, chitin and curdlan. Other derivatives are the creation of fluorescent derivatives that are used as markers in medical scanning procedures. Other products are the result of random polymerisation of sugar residues through the treatment of starch with acid under conditions of low water activity. Polydextrose is an example of this type of product. Classification I 5 Table 1 Classification of polysaccharides Origin Source Type Example Higher plants Trees Celluloses Cotton Hemicelluloses