Note: Intro -- Recent Trends in Carbohydrate Chemistry: Synthesis and Biomedical Applications of Glycans and Glycoconjugates -- Copyright -- Contents -- Contributors -- Preface -- Part One: Advances in chemical synthesis and biosynthesis of bacterial glycans -- 1: Prokaryotes: Sweet proteins do matter -- 1 Introduction -- 2 Cell surface (S-) layer glycoproteins -- 3 Bacteria -- 3.1 Lactic acid bacteria -- 3.1.1 Lactobacillus buchneri -- 3.1.2 Lactobacillus kefiri -- 3.2 Oral pathogens -- 3.2.1 Tannerella forsythia -- 3.2.2 Porphyromonas gingivalis -- 3.3 Other bacteria -- 3.3.1 Paenibacillus alvei -- 3.3.2 Bacillus anthracis -- 3.3.3 Kuenenia stuttgartiensis -- 3.3.4 Candidatus Brocadia -- 3.4 Archaea -- 3.4.1 Haloferax volcanii -- 3.4.2 Sulfolobus acidocaldarius -- 3.4.3 Antarctic haloarchaea -- 4 Flagella/Archaella and fimbriae -- 4.1 Bacteria -- 4.1.1 Paenibacillus alvei -- 4.1.2 Selenomonas sputigena -- 4.1.3 Porphyromonas gingivalis -- 4.2 Archaea -- 4.2.1 Haloferax volcanii -- 5 Adhesins, bacteriocins, invasins, and glycocins -- 5.1 Streptococcus gordonii -- 5.2 Streptococcus salivarius -- 5.3 Streptococcus agalactiae -- 5.4 Streptococcus mutans -- 5.5 Staphylococcus aureus -- 5.6 Enterococcus durans -- 5.7 Lactobacillus plantarum -- 5.8 Lactobacillus casei -- 5.9 Xanthomonas citri -- 5.10 Escherichia coli -- 5.11 Actinoplanes sp. -- 5.12 Trichomonas vaginalis -- 6 Spores -- 6.1 Bacillus anthracis -- 7 Concluding remarks -- References -- 2: Glycan ligation reactions in the periplasmic space -- 1 Introduction -- 2 WaaL O-antigen ligases -- 3 The ArnT family -- 4 Oligosaccharyl transferases -- 5 Conclusions -- References -- 3: Synthesis of bioactive lipid A and analogs -- 1 Lipid A-Structure, immunobiological function, and potential therapeutic significance. , 1.1 Lipopolysaccharide and lipid A are "pathogen-associated molecular patterns" -- 1.2 Lipid A regulates the innate immune signaling through "PRRs" TLR4 and caspase-4/11 -- 1.3 Structural diversity of lipid A -- 1.4 Challenges in endotoxin research and heterogeneity of lipid A -- 2 Synthesis of lipid A and analogs -- 2.1 Approaches toward the synthesis of lipid A variants -- 2.2 Synthesis of orthogonally protected β (1 → 6)-linked diglucosamine backbone of lipid A. Protective group manipul ... -- 2.3 Divergent s ynthesis of E. coli, S. typhimurium, and N. meningitidis lipid A -- 2.4 Synthesis of a library of P. gingivalis lipid A and analogs -- 2.5 Divergent synthesis of H. pylori lipid A variants -- 2.6 Synthesis of structurally unusual lipid A from Rhizobium sin-1 -- 3 Application of lipid A derivatives as vaccine adjuvants -- 3.1 Synthesis of MPLA variants as potential vaccine adjuvants -- 3.2 Application of MPLA as carrier molecule and "inbuilt" adjuvant for self-adjuvanting vaccine candidates -- 4 Synthesis of lipid A modified by addition of amino sugars at the glycosidic phosphate group -- 4.1 Synthetic challenges in the assembly of 1,1 ′ -glycosyl phosphodiesters -- 4.2 Galactosamine-modified Francisella lipid A -- 4.3 Synthesis of a neoglycoconjugate comprising GalN-modified Francisella lipid A backbone β GlcN(1 → 6)- α GlcN(1 ... -- 4.4 4-Amino-4-deoxy- β - l -arabinose ( β - l -Ara4N)-modified Burkholderia lipid A -- 4.5 Synthesis of a neoglycoconjugate entailing an epitope β GlcN(1 → 6)- α GlcN(1 → P←1)- β - l -Ara4N -- 4.6 Synthesis of 4-amino-4-deoxy- β - l -arabinose ( β - l -Ara4N)-modified Burkholderia lipid A -- 5 Conclusion -- References -- 4: Synthesis of lipopolysaccharide core fragments -- 1 Introduction -- 2 Synthesis of LPS inner core fragments -- 2.1 Recent approaches for Kdo α-glycoside formation. , 2.2 Synthesis of Kdo β-glycosides -- 2.3 Synthesis of LPS inner core fragments of Acinetobacter and Agrobacteria -- 2.4 Synthesis of inner core units containing Ko and Ara4N residues -- 2.5 Synthesis of heptose-containing core fragments -- 2.5.1 Synthesis of glycero-d-manno-heptoses -- 2.5.2 Synthesis of heptose-containing inner core units -- 2.6 Synthesis of Neisseria and Haemophilus core epitopes -- 3 Synthesis of outer core fragments -- 4 Conclusions -- Acknowledgment -- References -- 5: Synthesis of oligosaccharides related to potential bioterrorist pathogens -- 1 Introduction -- 2 Bacillus anthracis -- 3 Burkholderia pseudomallei and Burkholderia mallei -- 3.1 Capsular polysaccharides -- 3.2 Lipopolysaccharides -- 3.3 Exopolysaccharides -- 4 Francisella tularensis -- 5 Yersinia pestis -- 6 Brucella spp. -- 7 Conclusion -- References -- 6: Synthetic teichoic acid chemistry for vaccine applications -- 1 Introduction -- 2 Synthetic teichoic acids -- 2.1 S. aureus TAs -- 2.1.1 S. aureus LTA -- 2.1.2 S. aureus WTA -- 2.2 Enterococcal TAs -- 2.2.1 E. faecalis and E. faecium LTA -- 2.2.2 E. faecium WTA -- 2.3 C. difficile -- 2.3.1 C. difficile LTA (PSIII) -- 3 Conclusions -- References -- 7: NMR characterization of bacterial glycans and glycoconjugate vaccines -- 1 NMR characterization of carbohydrates -- 1.1 Carbohydrate NMR spectra -- 1.2 Assignment of NMR spectra of carbohydrates -- 2 NMR analysis of surface carbohydrates of gram-negative bacteria -- 2.1 Capsular polysaccharides -- 2.2 Lipopolysaccharide -- 2.2.1 Shigella O-antigens -- 2.2.2 Salmonella O-antigens -- 3 NMR analysis of surface carbohydrates of gram-positive bacteria -- 3.1 Surface carbohydrates of Streptococcus pneumoniae -- 3.2 Surface carbohydrates of group B Streptococcus -- 3.3 Surface carbohydrates of other gram-positive bacteria. , 4 NMR analysis of glycoconjugate vaccines -- 4.1 Preparation of glycoconjugate vaccines -- 4.2 NMR monitoring of the conjugation process -- 4.3 NMR characterization of glycoconjugate vaccines -- 5 Investigating antigen-antibody interactions using NMR spectroscopy -- 6 Conclusions -- Acknowledgments -- References -- Part Two: Synthetic carbohydrate-based vaccines: present and future -- 8: Glycoconjugate vaccines, production and characterization -- 1 Introduction -- 2 Conjugation chemistries -- 2.1 Classic methods for conjugation of natural polysaccharides and synthetic carbohydrates -- 2.2 Site-selective glycan-protein conjugation -- 2.3 Conjugation to nanoparticle carriers -- 3 Physicochemical characterization and quality control of glycoconjugate vaccines -- 4 Conclusions -- Disclosures -- References -- 9: Antifungal glycoconjugate vaccines -- 1 Introduction -- 2 Major human fungal pathogens -- 3 Carbohydrates in the molecular architecture of fungal CWs -- 4 Immunity against fungal pathogens -- 5 Glycoconjugates as antifungal vaccines -- 6 Glycoconjugates vaccines against Candida -- 7 Mannan glycoconjugates -- 8 β -Glucan glycoconjugates -- 9 Poly- N -acetyl-(1 → 6)- α -glucosamine glycoconjugates -- 10 Glycoconjugates vaccines against Aspergillus fumigatus -- 11 Glycoconjugates vaccines against Cryptococcus neoformans -- 12 Conclusion -- References -- 10: Site-selective conjugation chemistry for synthetic glycoconjugate vaccine development -- 1 Introduction -- 2 Homogeneous glycoprotein vaccine design -- 2.1 Classical bioconjugation methods -- 2.2 Modern methods targeting canonical amino acids -- 2.2.1 Lysine and N-terminus -- 2.2.2 Tyrosine -- 2.2.3 Cysteine and disulfides -- 2.3 Modern methods targeting noncanonical amino acids -- 2.3.1 Carbonyls -- 2.3.2 Alkynes, alkenes, and dipoles. , 2.4 Transition metal-mediated approaches -- 2.4.1 Canonical amino acids -- 2.4.2 Noncanonical amino acids -- 3 Conclusions and outlook -- Acknowledgments -- References -- 11: Glyconanoparticles as versatile platforms for vaccine development: A minireview -- 1 Glyconanoparticles based on inorganic core -- 1.1 Antiviral vaccines -- 1.2 Antibacterial vaccines -- 1.3 Anticancer vaccines -- 2 Glyconanoparticles based on polymeric core -- 3 Glyconanoparticles based on self-assembling core -- 4 Glyconanoparticles based on OMVs -- 5 Glyconanoparticles based on virus-like particles -- 6 Conclusions -- References -- Index.

Note: Intro -- Recent Trends in Carbohydrate Chemistry: Synthesis, Structure and Function of Carbohydrates -- Copyright -- Contents -- Contributors -- Preface -- Part One: Monosaccharide chemistry toward molecular diversity-Recent findings -- 1: Perspective on the transformation of carbohydrates under green and sustainable reaction conditions -- 1 Introduction -- 2 Synthetic transformations of carbohydrates using nonhazardous environmentally benign solvents -- 3 Transformations of carbohydrates in water -- 4 Transformations of carbohydrates in room temperature ionic liquids -- 5 Use of ionic liquids as reaction solvents -- 6 Ionic liquid tags in enzymatic reactions -- 7 Transformation of carbohydrates in supercritical fluids -- 8 Transformation of carbohydrates in deep eutectic solvents -- 9 Transformation of carbohydrates using fluorous solvents -- 10 Transformation of carbohydrates using nonconventional energy sources -- 11 Oligosaccharide synthesis using microwave irradiation -- 12 Transformation of carbohydrates using ball milling -- 13 Sonication-assisted transformations of carbohydrates -- 14 Ultrasound-mediated functionalization of carbohydrates -- 15 Transformation of carbohydrates under photoinduced reactions -- 16 Photoinduced glycosylation -- 17 Photoinduced synthesis of S-linked glycoconjugates -- 18 Electrochemical glycosylation -- 19 Glycosylation under high pressure -- 20 Conclusion -- Acknowledgments -- References -- 2: 5-(Hydroxymethyl)furfural and 5-(glucosyloxymethyl)furfural in multicomponent reactions -- 1 Introduction -- 1.1 Multicomponent reactions -- 1.2 5-(Hydroxymethyl)furfural -- 1.3 5-( α -d-Glucosyloxymethyl)furfural -- 2 Biginelli-type reactions -- 3 Aza-Morita-Baylis-Hillman reaction -- 4 A 3 -coupling of bio-based furanic aldehydes -- 5 Ugi-type reactions -- 6 Kabachnik-Fields reaction. , 7 Multicomponent dipolar cycloadditions -- 8 Conclusion -- Acknowledgments -- References -- 3: Alkyne dicobalt complexes in carbohydrates: Synthetic applications -- 1 Introduction -- 2 Dicobalt hexacarbonyl-mediated anomerization of alkynyl C-glycosides -- 3 Dicobalt hexacarbonyl-mediated ring-opening of alkynyl C-glycosides -- 4 Dicobalt hexacarbonyl-mediated formation of ether rings from sugar acetylenes -- 5 Glycosylations based on alkyne dicobalt hexacarbonyl complexes -- 6 Dicobalt hexacarbonyl-mediated Ferrier(II)-type carbocyclizations from pyranose derivatives -- 7 Pyranosidic dicobalt hexacarbonyl propargyl oxycarbenium ions versus oxycarbenium ions-Some remarkable features -- 8 Dicobalt hexacarbonyl complexes of alkynyl compounds as precursors of pyranosidic Ferrier-Nicholas cations-Synthesi ... -- 8.1 Ferrier rearrangement or Ferrier(I) reaction-Ferrier- Nicholas cations -- 8.2 C1-Ferrier-Nicholas cations -- 8.3 C3-Ferrier-Nicholas cations -- 8.4 Ferrier-Nicholas systems based on (2-deoxy-2-C-methylenepyranosyl)alkynes -- 9 Conclusion -- Acknowledgments -- References -- 4: Gold-catalyzed methodologies in carbohydrate syntheses -- 1 History -- 2 Introduction -- 3 Gold catalysis in carbohydrate chemistry -- 4 Heterogeneous oxidation of carbohydrates using gold-catalysts -- 5 Homogeneous gold-catalysis in carbohydrate chemistry -- 6 2,2-Dimethylbut-3-ynyl thioglycosides as glycosyl donors -- 7 Activation of orthoesters -- 8 Activation of glycosyl esters -- 9 Activation of glycosyl carbonate -- 10 Synthesis of oligosaccharides -- 11 Gold-catalyzed synthesis of glycolipids -- 12 Gold-catalysis on carbohydrates for the total synthesis of biologically significant molecules -- 13 Conclusion -- Acknowledgments -- References -- 5: Glycomimetics with unnatural glycosidic linkages -- 1 Introduction. , 2 Carbohydrate mimetics with two-bond interglycosidic linkages -- 2.1 Thioglycosides -- 2.1.1 Introduction of sulfur to the anomeric position -- 2.1.2 Introduction of the thio-linkage to a non-anomeric position -- 2.2 Selenoglycosides -- 2.3 N-Glycosides and neoglycosides -- 2.4 C-Glycosides -- 3 Mimetics with three-bond interglycosidic connections -- 3.1 S-S, Se-S, Se-Se-linked mimetics -- 3.2 C-S, C-N, N-O, C-O, SO2-N-linked disaccharides -- 4 Mimetics linked by four-bond bridges -- 5 Conclusion -- References -- 6: Advancements in synthetic and structural studies of septanoside sugars -- 1 Introduction -- 2 Ring-closing reactions of linear precursors to septanoses -- 3 5-Exomethylene pyranoside precursors to septanoses -- 4 Cyclization of linear precursors with terminal diene functionalities -- 5 Septanose formation through fragment assembly of non-sugar precursors -- 6 Cyclopropanated pyrans as one-carbon intramolecular homologation synthons -- 7 Hydrolytic stability of the septanoside glycosidic bond -- 8 Solid-state structures of septanoses -- 9 Solution-phase structural studies of septanoses -- 10 Conclusion -- Acknowledgments -- References -- 7: N- and C-Glycopyranosyl heterocycles as glycogen phosphorylase inhibitors -- 1 Introduction -- 2 Syntheses -- 2.1 Five-membered N-(β-d-glucopyranosyl) heterocycles -- 2.1.1 Imidazoles -- 2.1.2 1,2,3-Triazoles -- 2.1.3 Tetrazoles -- 2.2 Five-membered C-(β-d-glucopyranosyl) heterocycles -- 2.2.1 2,6-Anhydroaldonic acid derivatives as precursors -- 2.2.2 Pyrroles -- 2.2.3 Isoxazoles -- 2.2.4 Pyrazoles -- 2.2.5 Thiazoles -- 2.2.6 Imidazoles -- 2.2.7 Oxadiazoles -- 2.2.8 1,3,4-Thiadiazoles -- 2.2.9 Triazoles -- 1,2,3-Triazoles -- 1,2,4-Triazoles -- 2.2.10 Tetrazoles -- 2.3 Annulated N-(β-d-glucopyranosyl) azoles -- 2.4 Annulated C-(β-d-glucopyranosyl) azoles. , 2.4.1 Indoles -- 2.4.2 Benzothiazoles -- 2.4.3 Annulated imidazoles -- Benzimidazoles and related compounds -- Further imidazo-fused heterocycles -- 2.5 Six-membered N-(β-d-glucopyranosyl) heterocycles -- 2.6 Six-membered C-(β-d-glucopyranosyl) heterocycles -- 2.7 N- and C-Glycopyranosyl heterocycles with modified sugar units -- 3 Glycogen phosphorylase inhibition -- 3.1 Five-membered N- and C-(β-d-glucopyranosyl) heterocycles -- 3.2 Six-membered N- and C-(β-d-glucopyranosyl) heterocycles -- 3.3 N- and C-Glycopyranosyl heterocycles with modified sugar units -- 4 Conclusion -- Acknowledgments -- References -- 8: Recent developments in synthetic methods for sugar phosphate analogs -- 1 Introduction -- 2 Sugar phosphonates -- 2.1 Anomeric sugar phosphonates -- 2.2 Nonanomeric sugar phosphonates -- 3 Glycosyl boranophosphates -- 4 Glycosyl thiophosphates and thiophosphonates -- 5 Glycophostones -- 6 Conclusion -- References -- Part Two: Structure-function relationships in polysaccharides -- 9: Synthetic polysaccharides -- 1 Introduction -- 1.1 Challenges in the chemical synthesis of polysaccharides -- 1.2 Alternatives to the chemical synthesis of polysaccharides -- 2 Polymerization reactions in polysaccharide synthesis -- 2.1 Condensation polymerization -- 2.1.1 Polycondensation of unprotected sugars -- 2.1.2 Polycondensation of protected sugars -- 2.1.3 Polycondensation of trityl ethers cyanoethylidene sugar derivatives -- 2.1.4 Condensation of sugar oxazolines -- 2.2 Ring-opening polymerization -- 2.2.1 ROP of anhydrosugars -- 1,6-Anhydrosugars -- 1,4-, 1,3-, and 1,2-Anhydrosugars -- Anhydrosugar dimers -- Unprotected anhydrosugars -- 2.2.2 ROP of tricyclic orthoesters -- 2.2.3 ROP of cyclodextrins (CDs) -- 3 Well-defined structures: Total synthesis -- 3.1 Solution-phase synthesis -- 3.1.1 Repetitive polysaccharides. , 3.1.2 Non-repetitive polysaccharides -- Synthesis of mycobacterial arabinogalactan -- Synthesis of mycobacterial lipoarabinomannan-related structures -- 3.2 Automated solid-phase synthesis -- 4 Conclusions -- References -- 10: Linear and cyclic amyloses: Beyond natural -- 1 Introduction -- 2 Preparation of linear and cyclic amyloses -- 2.1 Linear amylose and linear-amylose-containing polymers -- 2.2 Cyclic amylose -- 3 Conformation and dilute solution properties -- 3.1 Linear amylose -- 3.2 Cyclic amylose -- 4 Formation of complexes with guest molecules -- 5 Stability of amylose in aqueous solution -- 5.1 Self-assembly and double helix formation -- 5.2 Amylose gels -- 6 Progress toward the industrial application of LA and CA -- 6.1 Amylose films -- 6.1.1 Optical polarization properties of amylose-iodine films -- 6.1.2 Amylose-chitosan blend film -- 6.2 CA as an artificial chaperone for protein refolding -- 6.3 Amylose derivatives -- Acknowledgments -- References -- 11: Modification of xanthan in the ordered and disordered states -- 1 Introduction -- 2 Chemical structure -- 3 Conformation, order-disorder transition, and polyelectrolyte properties -- 4 Stability and degradation: Role of conformational states -- 4.1 Acid hydrolysis -- 5 Rheological properties -- 6 Chemical modification of xanthan -- 6.1 Chemical modification targeting both the alcohol and the acid function of xanthan -- 6.2 Chemical modification targeting the alcohol functions of xanthan -- 6.3 Chemical modification targeting the carboxylate functions of xanthan -- 7 Physicochemical properties of modified xanthan -- 8 Conclusions -- References -- Further reading -- 12: Derivatized polysaccharides on silica and hybridized with silica in chromatography and separation-A mini review -- 1 Introduction. , 2 Porous silica materials surface-modified with PS derivatives.

Note: Cover -- Half Title -- Series Page -- Title Page -- Copyright Page -- Dedication -- Contents -- Foreword -- Introduction -- About the Series Editor -- About the Editors -- Contributors -- PART I: SYNTHETIC METHODS -- Chapter 1: Synthesis of Glycosyl Thiols via 1,4-Dithiothreitol-Mediated Selective Anomeric S-Deacetylation -- Chapter 2: One-Step Transformation of Glycals into 1-Iodo Glycals -- Chapter 3: Optimized Henry Reaction Conditions for the Synthesis of an l-Fucose C-Glycosyl Derivative -- Chapter 4: Microwave-Assisted Synthesis of N-Substituted 1-Azido Glucuronamides -- Chapter 5: Click Approach to Lipoic Acid Glycoconjugates -- Chapter 6: Synthesis of N-Glucosyl Ethyl and Butyl Phosphoramidates -- Chapter 7: p-Tolyl 2,3,4,6-Tetra-O-Benzoyl-1-Thio-β-d-Galactopyranoside: Direct Synthesis from the Readily Available α-per-O-Benzoyl Derivative -- Chapter 8: One-Pot Chemoselective S- vs O-Deacetylation and Subsequent Thioetherification -- Chapter 9: Sakurai Anomeric Allylation of Methyl α-Pyranosides -- Chapter 10: Conversion of Simple Sugars to Highly Functionalized Fluorocyclopentanes -- Chapter 11: Carbene-Mediated Quaternarization of the Anomeric Position of Carbohydrates -- PART II: SYNTHETIC INTERMEDIATES -- Chapter 12: Glucose and Glucuronate 2,2,2-Trichloroethyl Sulfates: Precursors for Multiply Sulfated Oligosaccharides -- Chapter 13: Synthesis of Allyl α-(1→2)-Linked α-Mannobioside from a Common 1,2-Orthoacetate Precursor -- Chapter 14: Synthesis of 2I-O-Propargylcyclo-Maltoheptaose and Its Peracetylated and Hepta(6-O-Silylated) Derivatives -- Chapter 15: Synthesis of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-d-Galactopyranose -- Chapter 16: Regioselective Palladium Catalyzed Oxidation at C-3 of Methyl Glucoside -- Chapter 17: Synthesis of Dibenzyl 2,3,4,6-Tetra-O-Benzyl-α-D-Mannopyranosyl Phosphate. , Chapter 18: Synthesis and Characterization of (+)-3-C-Nitromethyl- 1,2:5,6-di-O-Isopropylidene-α-d-Allofuranose -- Chapter 19: Synthesis and Characterization of Propargyl 2,3,4,6-Tetra-O-Acetyl-β-d-Glucopyranoside -- Chapter 20: 3-(2′,3′,4′-Tri-O-Acetyl-α-l-Fucopyranosyl)-1-Propene -- Chapter 21: Synthesis and Characterization of 4-Methylphenyl 2,3,4,6- Tetra-O-Benzoyl-1-Thio-β-d-Galactopyranoside -- Chapter 22: Alternative Synthesis of 1,2,4,6-Tetra-O-Acetyl-3-Deoxy-3-Fluoro-α,β-d-Glucopyranose -- Chapter 23: Synthesis of Methyl 4-O-Benzoyl-2,3-O-Isopropylidene-α-d-Rhamnopyranoside: A Precursor to d-Perosamine -- Chapter 24: Synthesis of Allyl and Dec-9-Enyl α-d-Mannopyranosides from d-Mannose -- Chapter 25: Synthesis of 2,2,2-Trifluoroethyl Glucopyranoside and Mannopyranoside via Classical Fischer Glycosylation -- Chapter 26: Synthesis of 2-{2-[2-(N-Tert-Butyloxycarbonyl)Ethoxy]Ethoxy}Ethyl β-d-Glucopyranoside -- Chapter 27: Synthesis of 2-Propynyl 2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-1-Thio-β-d-Glucopyranoside, 2-Propynyl 3,4,6-Tri-O-Acetyl-2-Deoxy-2-Phthalimido-1-Thio-β-d-Glucopyranoside and Their 2-(2-Propynyloxy-ethoxy)ethyl Analogs -- Chapter 28: Synthesis of 1′-(4′-Thio-β-d-Ribofuranosyl) Uracil -- Chapter 29: Synthesis of an Orthogonally Protected l-Idose Derivative Using Hydroboration/Oxidation -- Chapter 30: 4-O-Acetyl-2-Azido-3,6-di-O-Benzyl-2-Deoxy-α/β-d-Glucopyranose -- Chapter 31: 2,3,4-Tri-O-Benzoyl-6-O-(Tert-Butyldiphenylsilyl)-1- Thio-β-d-Glucopyranose -- Chapter 32: Phenyl 2-Azido-4,6-di-O-Benzyl-2,3-Dideoxy-3-Fluoro-1-Thio-α- and β-d-Glucopyranosides -- Chapter 33: An Alternative Synthesis of 3-Azidopropyl 2,4,6-Tri-O- Benzyl-β-d-Galactopyranosyl-(1→4)-2,3,6-Tri-O-Benzyl- β-d-Glucopyranoside -- Index.

Note: Intro -- Anticarbohydrate Antibodies -- Preface -- Contents -- Contributors -- 1: Multidisciplinary Approaches to Study O-Antigen: Antibody Recognition in Support of the Development of Synthetic Carbohydrate-Based Enteric Vaccines -- 1.1 Introduction -- 1.2 Vibrio cholerae -- 1.2.1 LPSs as the Targets of Protection -- 1.2.2 Immune Recognition of Ogawa and Inaba LPSs -- 1.2.2.1 On the Antigenic Determinants -- Immunochemical Investigation Towards Ogawa and Inaba Common Antigenic Motifs -- Ogawa O-Ag Specificity Derived from Structural Analysis and Immunochemistry -- 1.2.2.2 On the Search for Potent Synthetic OS-Based Immunogens -- Vibrio cholerae O1 Serotype Ogawa -- Vibrio cholerae O1 Serotype Inaba -- 1.2.2.3 On the Quality of the Anti-LPS Ab Response -- 1.3 Shigella the Causing Agent of Bacillary Dysentery -- 1.3.1 On the Shigella O-Ag Targets -- 1.3.1.1 Need for a Pediatric Vaccine Against Prevalent Serotypes -- 1.3.1.2 dLPS Conjugates as Advanced Investigational Shigella Vaccines -- 1.3.1.3 Towards Better Standardized Shigella Glycoconjugate Vaccines -- 1.3.2 SD1: Knowledge and Hopes from Synthetic O-Ag Fragments -- 1.3.2.1 Molecular Modeling in Support to Immunochemistry to Uncover a SD1 Immunodominant Epitope -- 1.3.2.2 Synthetic OS-Protein Conjugates are more Potent Immunogens than Their dLPS-Protein Counterparts -- 1.3.3 S. flexneri: A Fabulous System Thanks to O-Ag Large Antigenic Diversity but High Chemical Similarity -- 1.3.3.1 α-d-Glucosylation and O-Acetylation as Sources of Serotype and Serogroup Specificity -- 1.3.3.2 Potential for Inducing Cross-Protective Abs: Insights Gained from Molecular Dynamics Simulations -- 1.3.3.3 Multidisciplinary Approaches to Identify SF5a Immunodominant Epitopes: On the α-d-Glcp-(13)-α-l-Rhap Branching Pattern -- Investigation on the Seric Immune Response. , Investigation on the Mucosal Immune Response: The Input of Secretory IgAs -- Is Short OS Antigenicity Predictive of Their Immunogenicity? -- 1.3.3.4 Multidisciplinary Approaches Towards Potent SFY O-Ag Mimics -- Combined Immunochemical, Physicochemical, Conformational and Structural Analysis to Identify SFY Immunodominant Epitopes -- On the Search for Functional Mimics of SFY O-Ag -- 1.3.3.5 Towards Potent SF2a Glycovaccines: The α-d-Glcp-(14)-α-l-Rhap Branching Pattern -- Combined Immunochemical and Physicochemical Analysis to Identify SF2a Immunodominant Epitopes -- On the Importance of OS Length for Ab Recognition: Input from Structural and Conformational Analysis -- Knowledge Gained from Immunological Studies: En Route Towards a Clinical Trial for the First SF2a Synthetic OS-Based Vaccine Canditate -- Future Prospects: The SF2a O-Ag is O-Acetylated -- 1.3.3.6 On the Road Towards a SF Glycovaccine in the Context of Multivalency -- 1.3.4 Conclusion and Perspectives: OS-Based Enteric Vaccines: Dream or Reality? -- References -- 2: Synthetic Oligosaccharide Bacterial Antigens to Produce Monoclonal Antibodies for Diagnosis and Treatment of Disease Using Bacillus anthracis as a Case Study -- 2.1 Introduction -- 2.2 The Anthrax Tetrasaccharide -- 2.2.1 Synthesis of Anthrax Tetrasaccharide 1 -- 2.2.2 Immunology -- 2.2.3 Analysis of Anthrax Carbohydrate-Antibody Interactions -- 2.3 The Anthrax Hexasaccharide -- 2.3.1 Synthesis of the Hexasaccharide Repeating Unit -- 2.3.2 Immunology -- 2.4 Conclusion and Outlook -- References -- 3: The Role of Sialic Acid in the Formation of Protective Conformational Bacterial Polysaccharide Epitopes -- 3.1 Introduction -- 3.2 Group B Neisseria meningitidis -- 3.2.1 Structure of the Group B Meningococcal Polysaccharide -- 3.2.2 Immunology of GBMP -- 3.2.3 Extended Helical Epitope of PSA. , 3.3 N-Propionylated PSA Conjugate Vaccine -- 3.3.1 Extended Helical Epitope of NPrPSA -- 3.3.2 Mimicked Protective Capsular Epitope -- 3.4 Group B Streptococcus -- 3.4.1 Structure of the Group B Streptococcus (GBS) Polysaccharides -- 3.4.2 Immunology of GBSP -- 3.4.3 Extended Helical Epitope of GBSPIII -- 3.4.4 GBSP Epitopes Independent of Sialic Acid Control -- 3.5 Concluding Remarks -- References -- 4: Antibody Recognition of Chlamydia LPS: Structural Insights of Inherited Immune Responses -- 4.1 Overview -- 4.2 The Antibody Response to Carbohydrate Antigens -- 4.3 The Specificity of Anti-Carbohydrate Antibodies -- 4.4 Structural Studies with Immunoglobulin Fragments -- 4.5 Early Structural Studies of Carbohydrate-Specific Antibodies -- 4.6 LPS as a Probe of the Antibody Response -- 4.7 Antibodies to Chlamydiaceae LPS -- 4.8 Chlamydial LPS as a Probe of the Antibody Response to Carbohydrates -- 4.9 Related Carbohydrate Antigens Induce the Same Germline Response -- 4.10 V-Region Restriction to Chlamydial Antigens -- 4.11 The Germline Pocket Binds Kdo Using Multiple Molecular Interactions -- 4.12 A Flexible Groove Accommodates Additional Carbohydrate Residues -- 4.13 S25-2 is Permissive to Modified Epitopes and Unnatural Antigens -- 4.14 S25-2 Utilizes an Unusual CDR L3 Canonical Conformation -- 4.15 Modest Levels of Somatic Mutation can Significantly Improve Binding -- 4.16 CDR H3 Significantly Affects Specificity -- 4.17 An Inward CDR H3 Tilt Precludes Binding of Certain Epitopes -- 4.18 An Outward Tilt to CDR H3 Encourages Cross-Reactivity -- 4.19 An Unusual CDR H3 Conformation Exposes Hydrophobic Residues -- 4.20 Antibody Specificity and Affinity Maturation -- 4.21 Induced Fit of CDR H3 in Antigen Recognition -- 4.22 Different V Gene Combinations Recognize Kdo-Based Antigens -- References. , 5: Designing a Candida albicans Conjugate Vaccine by Reverse Engineering Protective Monoclonal Antibodies -- 5.1 Introduction -- 5.2 Cell Wall Carbohydrate Antigens -- 5.3 Protection by Vaccines and Monoclonal Antibodies -- 5.3.1 Recognition Epitope -- 5.3.2 Epitope Mapping -- 5.3.3 Location of the Disaccharide Epitope -- 5.4 Designing a Conjugate Vaccine -- 5.4.1 Preparation of glycoconjugates -- 5.4.2 Induction of Anti-beta-Mannan Antibodies -- 5.4.3 Protection Experiments -- 5.4.4 Vaccination Reduces Candida Burden in Vital Organs -- 5.5 Efficacy of Trisaccharide Conjugate Vaccine in Mice -- References -- 6: The Neutralizing Anti-HIV Antibody 2G12 -- 6.1 The Anti HIV-1 Neutralizing Antibody 2G12 and It´s Neutralizing Activity -- 6.2 Binding of mAb 2G12 to gp120 -- 6.2.1 Glycans of HIV-1 gp120 -- 6.2.2 Analysis of the 2G12 Epitope -- 6.3 Structural Peculiarities of mAb 2G12 -- 6.4 Binding of Lectins -- 6.5 Expression and Large Scale Production of mAb 2G12 for Clinical Studies -- 6.6 Natural Development of mAb 2G12 and the Implications for Vaccine Design -- References -- 7: Immune Recognition of Parasite Glycans -- 7.1 Introduction -- 7.2 Trypanosomatids -- 7.2.1 Plasmodium (Malaria) -- 7.2.2 Entamoeba and Other Protozoa -- 7.3 Helminths -- 7.3.1 Schistosomes and Other Trematodes -- 7.3.1.1 Anti-Glycan Antibody Responses in Schistosomes: Host or Parasite Protective? -- 7.3.2 Cestodes -- 7.3.3 Nematodes -- 7.3.3.1 Ascarids -- 7.3.3.2 Filarial Parasites -- 7.3.3.3 Strongylid Parasites -- 7.3.3.4 The Trichuroid Group of Nematodes -- 7.4 General Implications of Parasite Glycans -- 7.4.1 Immunomodulatory Effects of Helminth Glycans -- 7.4.2 Diagnostic Applications for Helminth Glycans -- 7.5 Concluding Summary -- References -- 8: Human IgE Antibodies Against Cross-Reactive Carbohydrate Determinants -- 8.1 Introduction. , 8.2 Cross-Reactive Carbohydrate Determinants (CCDs): N-Linked Oligosaccharides with Core α(13)-Fucose and/or beta(12)-Xylose -- 8.2.1 Distribution and Structure of Allergenic N-Glycans -- 8.2.1.1 Cross-Reactive Carbohydrate Determinants of Plants -- 8.2.1.2 Cross-Reactive Carbohydrate Determinants of Insects/Insect Venoms -- 8.2.1.3 Cross-Reactive Carbohydrates of Other Invertebrates (Parasitic Helminths, Mollusks) -- 8.2.2 Specificity of Anti-CCD Antibodies -- 8.2.3 Prevalence and Origin of Anti-CCD IgE Antibodies in Allergic Patients -- 8.2.4 Clinical Significance of Anti-CCD IgE -- 8.2.5 Reasons for the Clinical Insignificance of CCDs -- 8.2.6 Diagnostic Implications of Anti-CCD IgE Antibodies -- 8.3 Allergenic O-Glycans -- 8.4 α-Gal, a Mammalian IgE-Binding Glycan -- 8.5 Summary -- References -- 9: Structural Glycobiology of Antibody Recognition in Xenotransplantation and Cancer Immunotherapy -- 9.1 Introduction -- 9.2 Antibody Recognition of Carbohydrate Xenoantigens -- 9.2.1 Structural Studies of Antibodies Against αGal Carbohydrate Xenoantigens -- 9.2.2 Potential Non-αGal Carbohydrate Xenoantigens -- 9.2.3 Progress Towards Clinical Xenotransplantation -- 9.3 Antibody Targeting of Tumor-Associated Carbohydrate Antigens -- 9.3.1 Recognition of Blood Group Related Lewis Carbohydrates by Antibodies -- 9.3.2 Antibody Recognition of Gangliosides -- 9.3.3 Other Antigens Resulting from Modified Glycosylation in Tumors -- 9.3.4 Potential Clinical Application for Antibody Targeting of Carbohydrates in Cancer -- 9.4 Concluding Remarks -- References -- 10: Carbohydrate Mimetic Peptide Vaccines: -- 10.1 Introduction -- 10.2 Nature of Carbohydrate-Binding Antibodies -- 10.2.1 IgM Antibodies at the Forefront -- 10.2.2 Affinity Maturation and Structural Consequences -- 10.2.3 A Case in Point. , 10.3 Molecular Mimicry Approach to Augment Anticarbohydrate Responses.