Stacey Obituary / P. Finch ; W.G. Overend |
Nomenclature of Carbohydrates / A.D. McNaught |
Thioglycosides as Glycosyl Donors in Oligosaccharide Synthesis / P.J. Garegg |
Dihexulose Dianhydrides / M. Manley-Harris ; G.N. Richards |
Sugars and Nucleotides and the Biosynthesis of Thiamine / S. David ; B. Estramareix |
Molecular Architecture of Polysaccharide Helices in Oriented Fibers / R. Chandrasekaran |
Sucrose Decomposition in Aqueous Solution, and Losses in Sugar Manufacture and Refining / M.A. Clarke ; L.A. Edye ; G. Eggleston |
Author Index |
Subject Index |
Nikolay Konstantinovich Kochetkov, 1915-2005 International Carbohydrate SymposiaA History / S. J. Angyal |
Mass Spectrometry Of Carbohydrates: Newer Aspects / J. A. Rodrigues ; A. M. Taylor ; D. P. Sumpton ; J. C. Reynolds ; R. Pickford ; J. Thomas-Oates |
Deoxy sugars: Occurrence and synthesis / R. M. de Lederkremer ; C. Marino |
Sucrose Chemistry and Applications of Sucrochemicals / Y. Queneau ; S. Jarosz ; B. Lewandowski ; J. Fitremann |
Anti-influenza Drug Discovery: Are we ready for the Next Pandemic? / T. Islam ; M. von Itzstein |
Chemoselective Neoglycosylation / F. Nicotra ; L. Cipolla ; F. Peri ; B. La Ferla ; C. Redaelli |
Hamao Umezawa 1914-11986 / T. Tsuchiya ; K. Maeda ; D. Horton |
Carba-Sugars Chemistry of (Pseudo-Sugars) and Their Derivatives / T. Suami ; S. Ogawa |
Chemistry and Developments of Fluorinated Carbohydrates |
Components of Bacterial Polysaccharides / B. Lindberg |
Glycoside Hydrolases: Mechanistic Information from Studies with Reversible and Irreversible Inhibitors / G. Legler |
Index |
Anthony Charles Richardson / Karl J. Hale |
Detection and Structural Characterization of Oxo-Chromium(V) Sugar Complexes by Electron Paramagnetic Resonance / Luis F. Sala ; Juan C. González ; Silvia I. García ; María I. Frascaroli ; Sabine Van Doorslaer |
Synthesis and Properties of Septanose Carbohydrates / Jaideep Saha ; Mark W. Peczuh |
Imino Sugars and Glycosyl Hydrolases: Historical Context, Current Aspects, Emerging Trends / Arnold E. Stütz ; Tanja M. Wrodnigg |
Contributors |
Preface |
Roger W. Jeanloz 1917-2007 / Nathan Sharon ; R. Colin Hughes |
Bengt Lindberg 1919-2008 / Lennart Kenne ; Olle Larm ; Alf Lindberg |
Zeolites and Other Silicon-Based Promoters in Carbohydrate Chemistry / Amélia P. Rauter ; Nuno M. Xavier ; Susana D. Lucas ; Miguel Santos |
Introduction / I: |
Zeolites, Clays, and Silica Gel as Heterogeneous Catalysts and Their Use in Organic Synthesis / II: |
Catalysis of Key Transformations in Carbohydrate Chemistry / III: |
Glycosylation / 1: |
Sugar Protection and Deprotection / 2: |
Hydrolysts/Isomerizalion of Saccharides and Glycosides / 3: |
Dehydration / 4: |
Oxidation / 5: |
Other Synthetic Applications / 6: |
Conclusion / IV: |
References |
Tools in Oligosaccharide Synthesis: Current Research and Application / Jürgen Seibel ; Klaus Buchholz |
Modified Enzymes and Substrates |
Glycosidases, Glycosynthases, Thioglycosidases |
Glucansucrases |
Fructansucrase Enzymes |
Sucrose Analogues |
Oligo-and Poly-saccharide Synthesis with Sucrose Analogues |
Sucrose Isomerase |
Commercial Products |
Acknowledgment |
Multivalent Lectin-Carbohydrate Interactions: Energetics and Mechanisms of Binding / Tarun K. Dam ; C. Fred Brewer |
Mucins: Background |
Binding of Lectins to Mucins |
Affinities of SBA and VML for Mucins |
Thermodynamics of SBA Binding Tn-PSM |
Thermodynamics of SBA Binding 81-mer Tn-PSM |
Thermodynamics of SBA Binding 38/40-mer Tn-PSM |
Thermodynamics of SBA Binding Fd-PSM |
Thermodynamics of VML Binding Tn-PSM |
Thermodynamics of VML Binding 81-mer Tn-PSM and 38/40-mer Tn-PSM / 7: |
Thermodynamics of VML Binding Fd-PSM / 8: |
Mechanisms of Binding of SBA and VML to PSM: The Bind and Jump Model |
Thermodynamics of Lectin-Mucin Crosslinking Interactions / V: |
Hill Plots Show Evidence of Increasing Negative Cooperativity |
Analysis of the Stoichiometry of Binding of SBA to the Mucins |
Crosslinking of Lectins with the Mucins Correlate with Decreasing Favorable Entropy of Binding |
Conclusions and Perspective / VI: |
The Bind and Jump Model for Lectin-Mucin Interactions |
Implications of Increasing Negative Cooperativity and Decreasing Favorable Binding Entropy of Lectins-Mucin Crosslinking Interactions |
Design and Creativity in Synthesis of Multivalent Neoglycoconjugates / Yoann M. Chabre ; René Roy |
Multivalency: Definition and Role |
Multivalency in Protein-Carbohydrate Interactions |
Synthesis and Applications of Multivalent Glycoconjugates |
Glycoclusters |
Glycoclusters from Branched Aliphatic Scaffolds |
Glycoclusters from Branched Aromatic Scaffolds |
Glycoclusters from Carbohydrate Scaffolds |
Glycoclusters from Peptide Scaffolds |
Other Glycoclusters |
Glycosylated Carbon-Based Nanostructures |
Glycofullerenes |
Glyconanotubes |
Multivalent Glycoconjugates by Self-Assembly |
Sell-Assembly Using Coordinating Metals |
Self-Assembly of Glycodendrons in Solution |
Glycodendrons and Glycodendrimers |
Glycodendrons |
Glyeodendrimers |
Jean Montreuil 1920-2010 / Jean-Claude Michalski |
Laurance David Hall 1938-2009 / Bruce Coxon |
Potential Trehalase Inhibitors: Syntheses of Trehazolin and its Analogues / Ahmed El. Nemr ; El Sayed H. El Ashry |
Natural Occurrence and Characterization of Trehazolin |
Biosynthesis of Trehazolin / IIII: |
Retrosynthetic Analysis of Trehazolin and Its Analogues |
Synthesis of the Sugar Isothiocyanate Fragment |
Synthesis of the Trehazolamine Fragment |
Synthesis from D-Glucose |
Synthesis from D-Mannose |
Synthesis from D-Ribose |
Synthesis from D-Arabinose |
Synthesis from D-Mannitol |
Synthesis from Sugar 1,5-Lactones |
Synthesis from myo-Inositol |
Synthesis from D-Ribonolactone |
Synthesis from Cyclopentadiene / 9: |
Synthesis from Acylated Oxazolidinones / 10: |
Synthesis from cis-2-Butene-1,4-diol / 11: |
Synthesis from Norbornyl Derivatives / 12: |
Synthesis from 3-Hydroxymethylpyridine / 13: |
Synthesis of Trehazolins / VII: |
Trehazolins Having Trehazolamines at the Anomeric Center |
Trehazolines with Trehazolamines on Positions Other than the Anomeric Center |
Synthesis of 1-Thiatrehazolin |
Deoxynojirimycin Analogues |
Acknowledgments |
Polysaccharides of the Red Algae / Anatolii I. Usov |
Storage Carbohydrates: Floridean Starch |
Neutral Structural Polysaccharides: Cellulose, Mannans, and Xylanp119 |
Sulfated Galactans |
General Information and Nomenclature |
Isolation of Galactans |
Chemical Methods of Structural Analysis |
Physicochemical Methods of Structural Analysis |
Enzymatic and Immunological Methods |
Polysaccharides of the Agar Group |
Polysaccharides of the Carrageenan Group |
DL-Hybrids |
Biological Activity of Sulfated Galactans |
Sulfated Mannans |
Glycuronans |
Heteropolysaccharides of Unicellular and Freshwater Red Algae. Miscellaneous Polysaccharides |
Algal Systematics and Polysaccharide Composition / VIII: |
Background |
Proteomics and Glycomics: Glycan Expression is Not Template-Driven |
Unmet Needs In Glycobiology and Glycotechnology |
Emerging Glycomics Technologies |
Progress In Mass Spectrometry|o234 |
The Rate-Determining Stage in Glycomics and Glycoproteomics |
Toward Automated Glycan Analysis |
Roy Lester Whistler 1912-2010 / James N. BeMiller |
Per Johan Garegg 1933-2008 / Stefan Oscarson |
Structure and Engineering of Celluloses / Serge Pérez ; Daniel Samain |
Cellulose in Its Cell-Wall Environment |
Conformations and Crystalline Structures of Cellulose |
Chemical Structure of the Cellulose Macromolecule |
Crystallinity and Polymorphism of Cellulose |
Crystalline Structures of Native Celluloses |
Cellulose II |
Cellulose III |
Cellulose IV |
Alkali Cellulose and Other Solvent Complexes |
Cellulose Acetate and Cellulose Derivatives |
Morphologies of Celluloses |
Polarity of Cellulose Crystals |
Crystalline Morphology of Native Celluloses |
Whiskers and Cellulose Microfibrils |
Surface Features of Cellulose |
Microfibril Organization |
Chemistry and Topochemistry of Cellulose |
Conditions for the Reactions of Cellulose |
Main Reactions Sites in Cellulose |
Etherification Reactions of Cellulose |
Acylation Reactions of Cellulose |
Deoxygenation of Cellulose |
Topochemistry of Cellulose |
Enzymatic Alterations and Modifications of Cellulose Fibers |
Tomorrow's Goal: An Economy Based on Cellulose |
Cellulose-Synthetic Polymer Composites |
Protective Films |
Cellulose-Cellulose Composites |
Conclusions |
Chemical Structure Analysis of Starch and Cellulose Derivatives / Petra Mischnick ; Dane Momcilovic |
History |
Polysaccharide Derivatives as Functional Polymers of Renewable Resources |
Chemical Modification of (1?4)-Glucans |
Cellulose |
Starch |
Kinetically Controlled Reactions |
Thermodynamically Controlled Reactions |
Structural Complexity of Glucan Derivatives |
Structure Analysis of (1?4)-Glucan Derivatives |
Average Degree of Substitution |
Monomer Composition: Substituent Distribution in the Glucose Residue |
Distribution of Monomer Residues along the Polymer Chain |
Heterogeneities in the Bulk Material |
Summary and Perspectives for the Future |
Glyconanoparticles: Polyvalent Tools to Study Carbohydrate-based Interactions / Marco Marradi ; Manuel MartÃn-Lomas ; Soledad Penadés |
Glyconanoparticles and Glyconanotechnology |
Glyconanoparticles: Synthesis, Characterization, and Types |
Noble-Metal Glyconanoparticles |
Magnetic GNPs |
Glyco Quantum Dots |
Applications of GNPs |
GNPs in Carbohydrate-Carbohydrate Interaction Studies |
GNPs in Carbohydrate-Protein Interactions |
Other Interaction Studies |
Glyconanoparticles as Antiadhesion Agents |
GNPs in Cellular and Molecular Imaging |
Other Applications of GNPs |
Future and Perspectives |
1-Amino-1-deoxy-D-fructose ("Fructosamine") and its Derivatives / Valeri V. Mossine ; Thomas P. Mawhinney |
Historical Perspective |
Nomenclature |
Methods of Formation |
Non-Enzymatic |
Enzymatic |
Structure and Reactivity |
Tautomers in the Solid State and Solutions |
Analytical Methods |
Acid/Base- and Metal-Promoted Reactions |
Enzyme-Catalyzed Reactions |
Fructosamines as Intermediates and Scaffolds |
The Maillard Reaction in Foods and in vivo |
Neoglycoconjugates |
Synthons |
Biological Functions and Therapeutic Potential |
Endogenous Fructosamines in Plants and Animals |
Fructosamines as Potential Pharma- and Nutra-ceuticals |
Concluding Remarks |
Sialidases in Vertebrates: A Family of Enzymes Tailored for Several Cell Functions / Eugenio Monti ; Erik Bonten ; Alessandra D' Azzo ; Roberto Bresciani ; Bruno Venerando ; Giuseppe Borsani ; Roland Schauer ; Guido Tettamanti |
The Lysosomal Sialidase NEU1 |
Lysosomal Routing and Formation of the Multienzyme Complex |
Human NEU1 Deficiency |
New Functions of NEU1 in Tissue Remodeling and Homeostasis |
Mouse Model of NEU1 Deficiency and Study of Disease Pathogenesis |
The Cytosolic Sialidase NEU2 |
General Properties of NEU2 |
Crystal Structure of Human Sialidase NEU2 |
Functional Implication of NEU2 |
The Plasma Membrane-Associated Sialidase NEU3 |
General Properties of NEU3 |
Functional Implication of NEU3 |
The Particulate Sialidase NEU4 |
General Properties of NEU4 |
Functional Implication of NEU4 |
Sialidases and Cancer |
Sialidases and Immunity |
Further Evidence for Possible Functional Implications of Sialidases |
in silico Analysis of Sialidase Gene Expression Patterns / IX: |
Amino Acid Sequence Variants in Human Sialidases / X: |
Sialidases in Teleosts / XI: |
Trans-Sialidases: What Distinguishes Them from Sialidases? / XII: |
Final Remarks / XIII: |
Gerald Aspinall, 1924-2005 / Robin Ferrier ; Mario A. Monteiro |
Vittorio Crescenzi, 1932-2007 / Roberto Rizzo |
Developments in the Karplus Equation as they Relate to the NMR Coupling Constants of Carbohydrates |
The Impact of Improved NMR Instrumentation |
The Impact of Molecular Modeling |
Vicinal Coupling Constants |
Proton-Proton Couplings |
Proton-Carbon Couplings |
Proton-Nitrogen Couplings |
Phosphorus Couplings |
Carbon-Carbon Couplings |
Other Types of Vicinal Couplings |
Fluorine Couplings |
Carbon-Tin Couplings |
Couplings Over Four Bonds |
Couplings Over Five Bonds |
Online Calculators for Coupling Constants and Torsions |
Summary |
Computational Studies of the Role of Glycopyranosyl Oxacarbenium Ions in Glycobiology and Glycochemistry / Dennis M. Whitfield |
Importance of Glycopyranosyl Oxacarbenium Ions |
Galactopyranosyl Oxacarbenium Ion as an Illustrative Model |
Isolated Cations-Ring and C-5-C-6 Side-Chain Conformations |
Facially Selective Methanol-Oxacarbenium Ion Complexes |
The Orientations and Conformations of Side Chains at C-2, C-3, C-4, and C-5 |
The Role of C-2-O-2 Rotations, Including Neighboring-Group Participation |
The Role of Proton Transfer in the Transition State for Glycosylation Reactions |
Differences in Ionization Between ?- and ?-Donors |
Conclusions and Future Directions |
Summary of Glycosylation Reaction Mechanisms |
Further Calculations Based on Existing Methodology |
Future Calculations Requiring Methodology Development |
Experimental Studies of Glycosylation |
Oligosaccharide Synthesis: From Conventional Methods to Modern Expeditious Strategies / James T. Smoot ; Alexei V. Demchenko |
Chemical Glycosylation and Conventional Oligosaccharide Synthesis |
Principles of Chemical Glycosylation |
Traditional Linear Oligosaccharide Synthesis |
Convergent Block Synthesis |
Selective (Leaving-Group Based) Strategies |
Selective Activation |
Two-Step Activation and the In situ Preactivation |
Active-Latent Strategy |
Orthogonal and Semi-orthogonal Strategies |
Deactivation by Steric Hindrance |
Temporary Deactivation Concept |
Chemoselective (Protecting-Group Based) Strategies |
Arming and Disarming with Neighboring Substituents |
Reactivity-Based Programmable Strategy |
Disarming by the Remote Substituents |
Disarming by Torsional Effects |
Super-Armed Glycosyl Donors |
Regioselectivity-Based Strategies |
Hydroxyl Reactivity |
Triphenylmethyl Reactivity |
Bidirectional Approaches |
Novel Technologies for the Rapid and High-Throughput Oligosaccharide Synthesis |
One-Pot Strategies |
Polymer-Supported, Solid-Phase, and Automated Synthesis |
Fluorous Tag-Supported and Microreactor Synthesis |
Enzymatic Approach |
Oligosaccharide Synthesis with Glycosyltransferases |
Oligosaccharide Synthesis with Glycosidases (Hydrolases) |
Outlook |
Stereocontrolled Synthesis of Mannans and Rhamnans / Feng Cai ; Baolin Wu ; David Crich |
The ?-Mannans and ?-Rhamnans |
?-Mannan Synthesis in the Absence of Neighboring-Group Participation |
Neighboring Group-Directed ?-Mannan Synthesis |
Synthesis of ?-Rhamnans |
?-Mannan Synthesis by Indirect Methods |
?-Rhamnan Synthesis by Indirect Methods |
?-Mannan Synthesis by Direct Methods |
?-Rhamnan Synthesis by Direct Methods |
Glycobiology of Trypanosoma cruzi / Rosa M. de Lederkremer ; Rosalia Agusti |
Life Cycle of the Parasite |
Specific Cell-Surface Glycoconjugates |
Glycoinositolphospholipids, Free and as Anchors of Proteins |
Trypanosoma cruzi Mucins |
T. cruzi Trans-sialidase (TcTS) |
Other Glycoproteins |
Combining Computational Chemistry and Crystallography for a Better Understanding of the Structure of Cellulose / Nathan Sharon 1925-2011 ; David Mirelman ; Edward A. Bayer ; Yair Reisner ; Alfred D. French |
Information from Crystals of Related Small Molecules |
Shape of the D-Glucopyranose Ring |
Linkage Geometry |
Conversion to Polymer-Shape Notation |
Orientation of O-6 |
Crystal Packing and Intermolecular Interactions |
Summary of Section on Extrapolation |
Energy Calculations |
Results on Individual Isolated Molecules with Empirical Methods |
Results with Quantum Methods |
Assessment of φψ Mapping |
Hydroxyl-Group Orientations |
Detection of New Stabilizing Interactions in Cellulose with Atoms-in-Molecules Theory |
Modeling Crystals of Cellulose |
Molecular Structure Drawings for Saccharide Analogues Having β-(l→4) Linkages / Appendix: |
Strategies in Synthesis of Heparin/Heparan Sulfate Oligosaccharides: 2000-Present / Steven B. Dulaney ; Xuefei Huang |
Challenges in Synthesis of Oligosaccharides of Heparin and HS |
Linear Synthesis |
Solution Phase |
Polymer-Supported Synthesis |
Active-Latent Glycosylation Strategy |
Reactivity-Based Chemoselective Glycosylation |
Reactivity-Independent, Pre-Activation-Based, Chemoselective Glycosylation |
Chemoenzymatic Synthesis |
Future Outlook |
Chemical Synthesis of Glycosylphosphatidylinositol Anchors / Benjamin M. Swarts ; Zhongwu Guo |
Classic Approaches to GPI Synthesis |
Synthesis of a Trypanosoma brucei GPI Anchor by the Ogawa Group (1991) |
Synthesis of a Yeast GPI Anchor by the Schmidt Group (1994) |
Synthesis of a Rat Brain Thy-1 GPI Anchor by the Fraser-Reid Group (1995) |
Synthesis of a T. brucei GPI Anchor by the Ley Group (1998) |
Synthesis of a Rat Brain Thy-1 GPI Anchor by- the Schmidt Group (1999, 2003) |
Synthesis of a Human Sperm CD52 Antigen GPI Anchor Containing an Acylated Inositol by the Guo Group (2003) |
Synthesis of a Plasmodium falciparum GPI Anchor Containing an Acylated Inositol by the Fraser-Reid Group (2004) |
Synthesis of a P. falciparum GPI Anchor Containing an Acylated Inositol by the Seeberger Group (2005) |
Synthesis of a T. cruzi GPI Anchor by the Vishwakarma Group (2005) |
Synthesis of a Fully Phosphorylated and Lipidated Human Sperm CD52 Antigen GPI Anchor by the Guo group (2007) |
Diversity-Oriented Approaches to GPI Synthesis |
Synthesis of T. cruzi GPI Anchors Containing Unsaturated Lipids by the Nikolaev Group (2006) |
Synthesis of a GPI Anchor Containing Unsaturated Lipid Chains by the Guo Group (2010) |
Synthesis of a Human Lymphocyte CD52 Antigen GPI Anchor Containing a Polyunsaturated Arachidonoyl Lipid by the Guo Group (2011) |
Synthesis of "Clickable" GPI Anchors by the Guo Group (2011) |
General Synthetic Strategy for Branched GPI Anchors by the Seeberger Group (2011) |
Conclusions and Outlook |
Effect of Protein Dynamics and Solvent in Ligand Recognition by Promiscuous Aminoglycoside-Modifying Enzymes / Engin H. Serpersu ; Adrianne L. Norris |
Aminoglycoside Antibiotics |
Aminoglycoside-Modifying Enzymes |
Thermodynamic Properties of Enzyme-AG Complexes |
Enthalpy, Entropy, and Gibbs Energy Changes for AG Binding |
Proton Linkage |
Heat-Capacity Changes |
Solvent Effects |
Protein Dynamics in Substrate Recognition and Substrate Promiscuity of AGMEs |
Conclusions and Future Considerations |
Molecular Architecture and Therapeutic Potential of Lectin Mimics / Yu Nakagawa ; Yukishige Ito |
Synthetic Lectin Mimics |
Molecular Architecture of Boronic Acid-Dependent Lectin Mimics |
Antiviral Potential of Boronic Acid-Dependent Lectin Mimics |
Molecular Architecture of Boronic Acid-Independent Lectin Mimics |
Antiviral and Antimicrobial Potential of Boronic Acid-Independent Lectin Mimics |
Naturally Occurring Lectin Mimics |
Antimicrobial and Carbohydrate-Binding Profiles of Pradimicins and Benanoimicins |
Molecular Basis of Carbohydrate Recognition by PRMs |
Antiviral Profile and Mode of Action of Pradimicins |
Conclusion and Future Prospects |
Enzymatic Conversions of Starch / Piotr Tomasik ; Derek Horton |
Introduction and General Remarks |
Historical Background |
Former Reviews |
Enzymes and Microorganisms for Conversion of Starch |
Alpha Amylases (EC 3.2.1.1) |
Beta Amylases (EC 3.2.1.2) |
Glucoamylase (EC 3.2.1.3) |
Other Amylases |
α-Glucosidase (EC 3.2.1.20) |
Pullulanase (EC 3.2.1.41) |
Neopullulanase (EC 3.2.1.135) |
Isoamylase (EC3.2.1.68) |
Other Hydrolases |
Enzymatic Cocktails |
Glycosyltransferases (EC 2.4.1) |
Microorganisms |
Hydrolysis Pathways and Mechanisms |
Role of Adsorption |
Mechanism of Inhibition |
Mathematical Models of Enzymatic Hydrolysis |
Effect of Light, Microwaves, and External Electric Field |
Kinetics |
Amylolytic Starch Conversions |
Pulping |
Malting |
Mashing |
Liquefaction |
Saccharification |
Effect of the Botanical Origin of Starch |
Role of Starch Pretreatment |
Role of Temperature |
Role of the Substrate Concentration |
Role of Water |
Role of Elevated Pressure |
Role of pH |
Role of Admixed Inorganic Salts / 14: |
Role of Inhibitors / 15: |
Stimulators of Hydrolysis / 16: |
Engineering Problems / 17: |
Applications of the Enzymatic Processes / 18: |
Starch as a Feedstock for Fermentations |
General Remarks on Fermentation |
Alcohol and Alcohol-Acetone Fermentations |
Carboxylic Acid Fermentations |
Nonamylolytic Starch Conversions |
Esterification and Hydrolysis |
Methanogenic and Biosulfidogenic Conversions |
Isomerization |
Hydrogen Production |
Trehalose |
Bacterial Polyester Formation |
Branching of Starch |
Polymerization |
Cyclodextrins |
Starch Metabolism in Human and Animal Organisms |
Digestible Starch |
Resistant Starch |
Starch Analytics Involving Enzymes |
Starch Evaluation and Analysis |
Enzyme Evaluation |