Note: Front Cover -- Advances in Carbohydrate Chemistry and Biochemistry -- Copyright -- Contents -- Contributors -- Preface -- Reference -- Robert John (Robin) Ferrier -- Bibliography -- Chapter Two: Synthetic Approaches to l-Iduronic Acid and l-Idose: Key Building Blocks for the Preparation of Glycosaminog... -- 1. Introduction -- 1.1. Background -- 2. Epimerization at C-5 of d-Glucose Derivatives -- 2.1. SN2 Displacement of Sulfonates -- 2.2. The Mitsunobu Reaction -- 2.3. Epimerization via Generation of a C-5 Radical -- 3. Homologation of Tetroses and Pentoses -- 3.1. The Mukaiyama-Type Aldol Reaction -- 3.2. Diastereoselective Cyanohydrin Formation -- 3.3. Addition of Organometallic Reagents -- 3.4. Homologation Using 2-(Trimethylsilyl)thiazole -- 4. Isomerization of Unsaturated Sugars -- 4.1. Diastereoselective Hydroboration of exo-Glycals -- 4.2. From Delta4-Uronates -- 4.3. From 4-Deoxypentenosides -- 4.4. From d-Glucuronic Acid Glycal -- 5. Miscellaneous Methods -- 5.1. Diastereoselective Tishchenko Reaction -- 5.2. Homologation with 5,6-Dihydro-1,4-dithiin-2-yl[(4-methoxybenzyl)oxy]methane -- 5.3. C-H Activation of 6-Deoxy-l-hexoses -- 6. Conclusions -- Acknowledgments -- References -- Chapter Three: Glycosylation of Cellulases: Engineering Better Enzymes for Biofuels -- 1. Introduction -- 2. Glycosylation of Cellulose-Degrading Enzymes -- 2.1. Introduction -- 2.2. Glycan Structures Found on TrCel7A and Additional Secreted Cellulases -- 2.3. Implications of N-Glycosylation of the TrCel7A Catalytic Domain -- 2.4. Implications of O-Glycosylation of TrCel7A Linker Domain -- 2.5. Implications of O-Glycosylation of the CBM -- 3. Recombinant Expression of Fungal Cellulases -- 3.1. Expression of T. reesei Cellulases in Saccharomyces cerevisiae -- 3.2. Glycoengineered Strains of and Heterologous Protein Expression in Pichia pastoris. , 3.3. Glycosylation and Engineering of Expressed Proteins in Aspergillus Species -- 4. Modifications by Glycan-Trimming Enzymes -- 4.1. Introduction -- 4.2. Secreted Glycan-Active α-Mannosidases from T. reesei -- 4.3. Secreted α-Mannosidases from Additional Fungi -- 4.4. endo-β-N-Acetylglucosaminidases Secreted by Fungi -- 5. Summary and Future Perspectives -- Acknowledgments -- Appendix 1. Molecular Dynamics Simulation of a Linker Interacting with Crystalline Cellulose -- References -- Chapter Four: Human Milk Oligosaccharides (HMOS): Structure, Function, and Enzyme-Catalyzed Synthesis -- 1. Introduction -- 2. Structures of HMOS -- 2.1. HMOS Monosaccharide Building Blocks, Core Structures, and Glycosidic Linkages -- 2.2. HMOS Structures -- 3. Biosynthesis of HMOS -- 4. Functions of HMOS -- 4.1. Neutral Non-Fucosylated HMOS -- 4.2. Fucosylated HMOS -- 4.3. Sialylated HMOS -- 5. Production of HMOS by Enzyme-Catalyzed Processes -- 5.1. 2FL -- 5.2. 3SL and 3SLN -- 5.3. 6SL and 6SLN -- 5.4. LNT2, LNnT, LNnH, LNnO, LNnD, LSTd, and Disialyl Oligosaccharides -- 5.5. Fucα1-2LNnT -- 5.6. LNFP III, LNnFP V, and LNnDFH -- 5.7. LNT -- 5.8. 3FL, LDFT, LNFP II, Lea Tetrasaccharide, and LeX Tetrasaccharide -- 5.9. LNFP I and LNDFH I -- 5.10. Other Oligosaccharides -- 6. Perspectives -- Acknowledgments -- References -- Author Index -- Subject Index -- Back Cover.

Note: Front Cover -- Advances in Carbohydrate Chemistry and Biochemistry -- Copyright -- Contents -- Contributors -- Preface -- Chapter One: Stevia Glycosides: Chemical and Enzymatic Modifications of Their Carbohydrate Moieties to Improve the Sweet- ... -- 1. Introduction -- 2. Steviol Glycoside Structures from S. rebaudiana -- 3. Steviol Variants of Glycoside Structures from S. rebaudiana -- 4. Stability of Steviol Glycosides -- 5. Structure-Sweetness Relationship -- 6. Chemical Modifications of Steviol Glycosides -- 7. Enzymatic Modifications of Steviol Glycosides -- 7.1. Cyclodextrin Glycosyl Transferase Systems -- 7.2. α-Glucosidase Transglycosylation Systems -- 7.3. β-Glucosidase Transglycosylation and Deglycosylation Systems -- 7.4. α-Galactosidase Transglycosylation Systems -- 7.5. β-Galactosidase Transglycosylation Systems -- 7.6. β-Fructosidase Transglycosylation Systems -- 7.7. β-Glycosyltransferase Glycosylation Systems Using UDP-Sugars -- 8. Patents Regarding Enzymatic Modifications of Steviol Glycosides -- 9. Concluding Remarks -- Addendum -- Acknowledgments -- References -- Chapter Two: Endoglycosidases for the Synthesis of Polysaccharides and Glycoconjugates -- 1. Introduction -- 1.1. Biological Functions of Glycans and Glycoconjugates -- 1.2. Synthetic Glycans and Glycoconjugates for Deciphering Functions -- 1.3. Enzymes as a Tool for the Synthesis of Glycans and Glycoconjugates -- 2. Endoglycosidases in the Synthesis of Natural and Artificial Polysaccharides -- 2.1. Synthesis of Artificial Cellulose and Derivatives via Enzymatic Polymerization of Glycosyl Fluorides Catalyzed by Ce ... -- 2.2. Chitinase-Catalyzed Synthesis of Artificial Chitin and Derivatives Using Sugar Oxazolines as Activated Substrates -- 2.3. Hyaluronidase-Catalyzed Construction of Glycosaminoglycans Using Sugar Oxazoline as the Activated Substrates. , 2.4. Endo-β-Xylosidase-Catalyzed Transglycosylation in the Synthesis of Proteoglycans -- 3. Endoglycosidases in the Synthesis of N-Glycopeptides and N-Glycoproteins -- 3.1. Exploration of Glycan Oxazolines as Donor Substrates for ENGase-Catalyzed Synthesis of Complex Glycopeptides and Gly ... -- 3.2. Generation of ENGase-Based Glycosynthases for Transglycosylation -- 3.3. ENGase-Catalyzed Synthesis of Selected Biologically Interesting Glycopeptides and Glycoproteins -- 3.4. ENGase-Catalyzed Transglycosylation for Glycosylation Remodeling of Therapeutic Monoclonal Antibodies -- 4. Endoglycosidases for the Synthesis of Neoglycolipids and Glycosphingolipids -- 4.1. Ceramide Glycanase-Catalyzed Transglycosylation for Glycolipid Synthesis -- 4.2. Endoglycoceramidase-Based Glycosynthase for the Synthesis of Glycosphingolipids -- 5. Concluding Remarks -- Acknowledgment -- References -- Chapter Three: Recent Advances Toward Robust N-Protecting Groups for Glucosamine as Required for Glycosylation Strategies -- 1. Introduction -- 2. The Glycosylation Reaction -- 3. Acyclic N-Protecting Groups -- 3.1. The Acetyl (Ac) Group -- 3.2. The Diacetyl [-N(Ac)2] Group -- 3.3. The Chloroacetyl (ClCH2CO) Group -- 3.4. The Dichloroacetyl Group -- 3.5. The Trichloroacetyl (TCA) and Trifluoroacetyl (TFA) Groups -- 3.6. The Pent-4-enoyl Group -- 3.7. The Trichloroethoxycarbonyl (Teoc) Group -- 3.8. The 2,2,2-Trichloro-1,1-dimethylethyloxycarbonyl (TCBOC) Group -- 3.9. The Allyloxycarbonyl (AOC) Group -- 3.10. The Benzyloxycarbonyl (Cbz or Z) Group -- 3.11. The p-Nitrobenzyloxycarbonyl (PNZ) Group -- 3.12. The Methoxycarbonyl Group -- 3.13. The Ethoxycarbonyl, Chloroethyloxycarbonyl, and Phenyloxycarbonyl Groups -- 3.14. The (1,3-Dimethyl-2,4,6-(1H,3H,5H)-trioxopyrimidin-5-ylidene)methyl (DTPM) Group -- 3.15. The 4,4-Dimethyl-2,6-dioxocyclohexylidenemethyl (Dde) Group. , 3.16. The N-2,4-Dinitrophenyl (DNP) Group -- 3.17. The Diphenylphosphoryl (DPPO) and Dimethylphosphoryl (DMPO) Groups -- 3.18. The N-Alkylacetamido Groups -- 3.19. Fluorous-Protecting Groups (Froc) -- 4. Cyclic N-Protecting Groups -- 4.1. Oxazolines -- 4.1.1. Methyloxazoline -- 4.1.2. Phenyloxazoline -- 4.1.3. 2-Alkoxy Glyco-[2,1-d]-2-oxazolines -- 4.2. Nonparticipating Groups -- 4.2.1. The 2,3-Oxazolidinone Group -- 4.2.2. The 2,5-Dimethylpyrrole Group (DMP) -- 4.3. Participating Groups -- 4.3.1. Five-Membered Ring Groups -- 4.3.1.1. The Phthalimido Family -- 4.3.1.2. The Dithiasuccinyl Group (Dts) -- 4.3.1.3. The Dimethylmaleoyl (DMM) Group -- 4.3.1.3.1. Formation of β Glycosides -- 4.3.1.3.2. Transformation of N-DMM to NHAc -- 4.3.1.3.3. β-(1→4)-Mannosyl-Linked Chitobiose-Type Compounds -- 4.3.1.3.4. Glycolipid Synthesis -- 4.3.1.3.5. Glycosaminoglycan (GAG) Syntheses -- 4.3.1.3.6. N-DMM-Protected Glycosyl Iodides -- 4.3.1.3.7. N-DMM-Based Synthesis of Trehalosamines -- 4.3.1.3.8. Synthesis of Chitooligomers -- 4.3.1.3.9. Synthesis of Murin-Type Oligosaccharides -- 4.3.1.3.10. N-Glycan Syntheses -- 4.3.1.3.11. Human Milk Oligosaccharides (HMOs) -- 4.3.1.3.12. Galactofuranosyl-β-(1→4)-GlcNAc -- 4.3.1.3.13. Glycosylation of 3- and 4-OH-Free DMM-Protected d-Glucosamines and d-Allosamines -- 4.3.1.3.14. Solid-Phase Synthesis of N-Glycans and HMOs -- 4.3.1.4. The Diphenylmaleoyl (DPM) Group -- 4.3.2. Six-Membered Ring Groups -- 4.3.2.1. The Thiodiglycolyl (TDG) Group -- 4.3.2.2. The Dimethylglutaroyl (DMG) Group -- 4.3.2.3. The Diglycolyl (DG) Group -- 5. Latent Amino-Protecting Groups -- 5.1. The Azido Glycosylation Method -- 5.2. 2-Nitro Sugars -- 5.2.1. 2-Nitro Glycals -- 5.2.1.1. O-Glycosides via Michael-Type Addition -- 5.2.1.2. Synthesis of N-Nucleosides -- 5.2.1.3. Synthesis of Glycosyl Phosphonates. , 5.2.1.4. Synthesis of β-C-Glycosyl Compounds (``β-C-Glycosides´´) -- 5.2.2. 2-Nitro-1-thioglycosyl Donors -- 6. Conclusions -- Acknowledgments -- References -- Chapter Four: Carbohydrate-Processing Enzymes of the Lysosome: Diseases Caused by Misfolded Mutants and Sugar Mimetics as ... -- 1. Introduction -- 2. Carbohydrate-Processing Enzymes of the Glycosphingolipid Degradation Pathway -- 2.1. Lysosomal β-d-Galactosidase -- 2.2. Lysosomal N-Acetyl-β-d-hexosaminidase -- 2.3. Lysosomal α-d-Galactosidase -- 2.4. Arylsulfatase A -- 2.5. Lysosomal β-d-Galactocerebrosidase -- 3. Lysosomal Glycogen Degradation and Glycogen Storage Disease -- 3.1. Lysosomal α-d-Glucosidase -- 4. Enzymes of the Glycoprotein Degradation Pathway and Glycoproteinoses -- 4.1. Lysosomal α-l-Fucosidase -- 4.2. Neuraminidase 1 -- 4.3. N-Acetyl-α-d-galactosaminidase -- 4.4. Lysosomal α-d-Mannosidase -- 4.5. Lysosomal β-d-Mannosidase -- 4.6. Aspartyl-N-acetyl-d-glucosaminidase -- 5. Enzymes Involved in Mucopolysaccharide Degradation and Mucopolysaccharidoses -- 5.1. Lysosomal α-l-Iduronidase -- 5.2. Lysosomal Heparan-N-sulfatase -- 5.3. Lysosomal N-Acetyl-α-d-glucosaminidase -- 5.4. Heparin Acetyl-CoA:α-d-glucosaminide-N-acetyltransferase -- 5.5. Lysosomal N-Acetyl-d-glucosamine-6-sulfatase -- 5.6. Lysosomal N-Acetyl-d-galactosamine-6-sulfatase -- 5.7. N-Acetyl-d-galactosamine-4-sulfatase (Arylsulfatase B) -- 5.8. Lysosomal β-Glucuronidase -- 5.9. Lysosomal Hyaluronidase -- 6. Conclusions and Outlook -- References -- Author Index -- Subject Index -- Back Cover.

Note: Front Cover -- Advances in Carbohydrate Chemistry and Biochemistry -- Copyright -- Contents -- Contributors -- Preface -- Chapter One: Hyaluronan and Hyaluronan Fragments -- 1. Introduction -- 2. HA in the Solid State and at Surfaces -- 3. HA in Dilute and in Crowded Solutions -- 4. HA Self-association -- 5. HA Size and Why It Matters -- 5.1. High-Molecular-Mass HA Is the Physiological Protector of Cells -- 5.2. Low-Molecular-Mass HA Stimulates Defensive Cellular Responses -- 5.3. Mechanisms for HA Degradation -- 5.3.1. Hyaluronidases -- 5.3.2. Degradation of HA by ROS/RNS -- 5.3.3. Degradation of HA by Other Chemical and Physical Means -- 6. Experimental Determination of HA Content and Size In Vivo -- 6.1. Isolation Methods -- 6.2. Specific Quantification Methods -- 6.3. Methods for Molecular Mass Analysis -- 6.4. Experimental Findings on HA Content and Size -- 6.4.1. HA in Biological Fluids -- 6.4.2. HA in Tissues -- 7. Diagnostic and Therapeutic Applications -- 7.1. Exogenous HA -- 7.2. HA-Based Medical Diagnostics -- 7.3. Therapeutic Modulation of HA Signaling -- Acknowledgments -- References -- Chapter Two: Application of Porous Materials to Carbohydrate Chemistry and Glycoscience -- 1. Introduction -- 2. Glycoproteins, Glycans, and Glycosylation -- 3. Characteristics of Porous Materials -- 4. Methods for Characterizing Porous Materials -- 5. Glycan and Carbohydrate Enrichment -- 6. Mesoporous Silica and Related Materials -- 6.1. Basic Aspects of Mesoporous Silicas -- 6.2. General Applications of Mesoporous and Porous Silica to Glycans -- 6.3. Mesoporous and Porous Silicas Modified for Boronate Affinity Applications -- 6.4. Carbon-Mesoporous Silica Composites -- 6.5. Lectin-Modified Porous Silica -- 6.6. Controlled Release Applications Involving Mesoporous Silica and Glycans -- 7. Porous Alumina -- 8. Porous Titania -- 9. Mesoporous Carbon. , 10. Porous Graphitic Carbon -- 11. Porous Polymers Interacting With or Modified by Carbohydrates -- 11.1. Boronate-Modified Porous Polymers -- 11.2. Hydrophilic Interactions on Porous Polymers -- 11.3. Glycan Release by Enzyme-Modified Porous Polymers -- 11.4. Porous Polymers Modified by or Interacting With Lectins -- 12. Nanoporous Gold -- 13. Future Directions -- Acknowledgments -- References -- Chapter Three: The Synthesis and Biological Characterization of Acetal-Free Mimics of the Tumor-Associated Carbohydrate A ... -- 1. Introduction -- 2. Cancer and Immunotherapy -- 2.1. Overview -- 2.2. TACAs in Cancer -- 3. Synthesis of the Natural TACAs: Historical Overview -- 3.1. Tn Antigen -- 3.2. TF Antigen -- 3.3. sTn Antigen -- 4. Synthetic TACA Antigens as Potential Immunotherapeutics -- 4.1. Overview of Current State of TACA Therapies -- 4.2. Challenges in TACA Vaccine Preparation -- 4.3. Acetal-Free Carbohydrate Antigens -- 5. Synthesis of Carbasugars -- 5.1. Overview -- 5.2. Diels-Alder Approach -- 5.2.1. McCasland Synthesis -- 5.2.2. Ogawa Synthesis -- 5.3. Chemoenzymatic Processes -- 5.4. Ring-Closing Metathesis -- 5.5. Ferrier Type II Rearrangements -- 5.6. Radical Cyclization -- 6. Synthesis of C-Glycosides -- 6.1. Cross-Coupling -- 6.1.1. Heck Reaction -- 6.1.2. Suzuki-Miyaura Coupling -- 6.1.3. Negishi Coupling -- 6.2. Ring-Closing Metathesis -- 6.3. Radical Tethering -- 6.4. Allylation and Related Reactions -- 7. Synthesis of Acetal-Free Tn Antigens -- 8. Synthesis of Acetal-Free TF Antigens -- 9. Synthesis of Acetal-Free sTn Antigens -- 10. Partial Synthesis of Acetal-Free Sialyl Lewis Antigens -- 11. Biological Conjugation and Biological Evaluation of Acetal-Free Mimics -- 11.1. Tn Antigen -- 11.2. TF Antigen -- 11.3. sTn Antigen -- 12. Conclusions and Perspectives -- Acknowledgments -- References -- Author Index -- Subject Index. , Back Cover.