Keywords:
Carbohydrates-Biotechnology.
;
Electronic books.
Description / Table of Contents:
Synthetic Glycomes aims to provide a comprehensive review of the current state of the synthetic glycome, synthetic strategies toward generating glycans with comprehensive structures, as well as the glycoarrays to unveil the glycan functions.
Type of Medium:
Online Resource
Pages:
1 online resource (487 pages)
Edition:
1st ed.
ISBN:
9781788017770
Series Statement:
Issn Series
URL:
https://ebookcentral.proquest.com/lib/geomar/detail.action?docID=5754672
DDC:
572.56
Language:
English
Note:
Cover -- Synthetic Glycomes -- Preface -- Contents -- Chapter 1 - Introduction: Glycome and theGlyco-toolbox -- 1.1 Introduction -- 1.2 Diversity of Glycans -- 1.3 Limited Glycan Backbone Structures -- 1.4 Access -- 1.5 Application -- 1.6 Conclusion -- References -- Chapter 2 - Methodologies in Chemical Syntheses of Carbohydrates -- 2.1 Introduction -- 2.2 Before Glycosylation -- 2.2.1 Protecting Groups -- 2.2.2 De Novo Syntheses of Carbohydrates -- 2.3 Amidst Glycosylation -- 2.3.1 Reactivity -- 2.3.2 Stereochemistry -- 2.4 Applications Beyond Glycosylation -- 2.4.1 Oligosaccharides and Polysaccharides -- 2.4.2 Glycoconjugates -- 2.4.3 Natural Products -- 2.5 Conclusion -- References -- Chapter 3 - Synthetically Useful Glycosyltransferases for the Access of Mammalian Glycomes -- 3.1 Introduction -- 3.2 Glycosyltransferases (GTs) and Their Usage in Mammalian Glycan Preparation -- 3.2.1 Leloir GTs and Non-LeloirGTs -- 3.2.2 Mammalian GTs and Bacterial GTs -- 3.2.3 Wild-typeGTs and Engineered GTs -- 3.3 Synthetically Useful Glycosyltransferases -- 3.3.1 N-Acetylglucosaminyltransferases(GlcNAcTs) -- 3.3.2 Galactosyltransferases (GalTs) -- 3.3.3 Fucosyltransferases (FucTs) -- 3.3.4 Sialyltransferases (SiaTs) -- 3.3.5 N-Acetylgalactosaminyltransferases(GalNAcTs) -- 3.3.6 Glucuronosyltransferases (GlcATs) -- 3.3.7 Mannosyltransferases (ManTs) -- 3.4 Strategies in GT-catalyzed Glycan Syntheses -- 3.4.1 Direct GT-catalyzedReactions -- 3.4.2 GT-catalyzed Reaction with Sugar Nucleotide In Situ Regeneration -- 3.4.3 One-pot Multienzyme (OPME) Syntheses and Enzymatic Modular Assembly (EMA) -- 3.4.4 Whole-cellCatalysis -- 3.4.5 Living Cell Factory -- 3.5 Prospective -- References -- Chapter 4 - Chemical Synthesis of N-Glycans -- 4.1 Introduction -- 4.2 Chemical Synthesis of N-Glycans -- 4.2.1 Chemical Synthesis of Core Trisaccharide in N-Glycans.
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4.2.2 Chemical Synthesis of High-mannose Type N-Glycans -- 4.2.3 Chemical Synthesis of Hybrid Type N-Glycans -- 4.2.4 Chemical Synthesis of Complex Type N-Glycans -- 4.2.4.1 Synthesis of Symmetric Biantennary Complex Type N-Glycans -- 4.2.4.2 Synthesis of Symmetric Triantennary Complex Type N-Glycans -- 4.2.4.2.1 Synthesis of Symmetric 2,2,6-Armed Triantennary Complex Type N-Glycans -- 4.2.4.2.2 Synthesis of Symmetric 2,4,2-ArmedTriantennary Complex Type N-Glycans. -- 4.2.4.3 Synthesis of Symmetric Tetraantennary Complex Type N-Glycans -- 4.2.5 Synthesis of Neu5Ac-containing Complex Type N-Glycans -- 4.2.6 Synthesis of Asymmetric Complex Type N-Glycans -- 4.2.7 Synthesis of Bisecting Type N-Glycans -- 4.2.8 Synthesis of Core-fucosylated N-Glycans -- 4.3 Discussion -- 4.4 Summary -- References -- Chapter 5 - Chemoenzymatic Synthesis of N-Glycans -- 5.1 Introduction -- 5.2 Enzymes Employed in the Preparation of N-Glycans -- 5.2.1 Sialyltransferases -- 5.2.2 Galactosyltransferases -- 5.2.3 Fucosyltransferases -- 5.2.4 N-Acetylhexosaminyltransferases -- 5.2.5 Glycosidases -- 5.2.6 Glycosynthases -- 5.3 Enzymatic Preparation of N-Glycans -- 5.4 Chemoenzymatic Preparation of N-GlycanLibraries -- 5.4.1 A General Strategy for Chemoenzymatic Synthesis of Asymmetric Complex Type N-Glycans -- 5.4.2 Core Synthesis/Enzymatic Extension (CSEE) Strategy forthe Synthesis of Hybrid and Complex Type N-Glycans -- 5.4.3 Enzymatic Synthesis of Complex Type N-Glycansfrom One Chemically Prepared Precursor -- 5.5 Modular Synthesis of All Types of N-Glycans -- 5.6 Summary -- References -- Chapter 6 - Chemoenzymatic Synthesis of α-Dystroglycan O-Mannose Glycans -- 6.1 Introduction -- 6.2 Biosynthetic Pathway and Functional Roles of O-Mannose Glycans -- 6.2.1 Biosynthesis Pathway of O-MannosylGlycans -- 6.2.2 Dystroglycanopathies and Implicated Genes.
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6.2.3 Roles of O-Mannosylationin Tumor Metastasis -- 6.2.4 Function of Core M1 and M2 Structures -- 6.2.5 O-MannosylatedSubstrates Beyond α-DG -- 6.3 Synthesis of O-MannoseGlycans -- 6.3.1 Chemical or Chemoenzymatic Synthesis of Core M1 Structures -- 6.3.2 Chemical or Chemoenzymatic Synthesis of Core M2 O-Mannose Glycans -- 6.3.3 Chemical Synthesis of Phosphorylated Core M3 Trisaccharide -- 6.4 Conclusion -- Abbreviations -- Acknowledgement -- References -- Chapter 7 - Chemical Synthesis of Glycopeptides and Glycoproteins -- 7.1 Introduction -- 7.2 Synthesis of Glycopeptide -- 7.2.1 Synthesis of Polypeptide Chain -- 7.2.2 Synthesis of PSGL-1 -- 7.2.3 Synthesis of CD52 -- 7.3 Ligation Method -- 7.3.1 Basic Strategies -- 7.3.2 Glycopeptide Thioester Synthesis -- 7.4 Synthesis of O-linkedGlycoproteins -- 7.4.1 Synthesis of Antifreeze Glycoprotein -- 7.4.2 Synthesis of MUC2 Model -- 7.4.3 Synthesis of Interleukin-2 -- 7.5 Synthesis of N-linkedGlycoprotein -- 7.5.1 Strategies for N-linked Glycoprotein Synthesis -- 7.5.2 Synthesis of Human Interferon-β -- 7.5.3 Synthesis of TIM-3 -- 7.5.4 Synthesis of Ig Domain of Emmprin -- 7.6 Conclusion -- References -- Chapter 8 - Synthesis of Chondroitin Sulfate Oligosaccharides and Chondroitin Sulfate Glycopeptides -- 8.1 Introduction to Chondroitin Sulfate (CS) and Chondroitin Sulfate Proteoglycan (CSPG) -- 8.2 Chemical Synthesis of CS -- 8.2.1 General Synthetic Design for Chemical Synthesis of CS -- 8.2.2 Strategies Addressing N-protective Groups -- 8.2.2.1 Azide Protective Group -- 8.2.2.2 N-AcetamideGroup -- 8.2.2.3 N-Trichloroacetamide Group -- 8.2.2.4 N-Trifluoroacetamide -- 8.2.2.5 N-Tetrachlorophthalimide Group -- 8.2.2.6 Lactose Derived CS Mimetics -- 8.2.3 Semi-synthesisof CS, Expediting Building Block Preparation Using Natural Sources -- 8.2.4 Solid Phase Synthesis of CS Oligosaccharides.
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8.2.5 Chemical Synthesis of a CS Disaccharide Library and Biotinylated CS -- 8.2.6 Chemical Synthesis of Heterologous Sulfated CS Oligosaccharides -- 8.2.7 Chemical Synthesis of CS Oligosaccharides with Linkage Region -- 8.3 Chemoenzymatic Synthesis of CS Oligosaccharides -- 8.4 Chemical Synthesis of CS Glycopolymers and Glycoconjugates -- 8.5 Synthesis of CS Glycopeptide -- 8.6 Conclusions -- Abbreviations -- Acknowledgement -- References -- Chapter 9 - Chemoenzymatic Synthesis of Heparan Sulfate and Heparin -- 9.1 Introduction -- 9.1.1 Heparan Sulfate -- 9.1.2 Heparin -- 9.1.3 Chemoenzymatic Synthesis of HS and Heparin -- 9.2 Key Techniques of Synthesis -- 9.2.1 Design of Sugar Nucleotides for the Chemoenzymatic Synthesis of HS -- 9.2.2 Sequences of Enzymatic Modifications for the Synthesis of Different Oligosaccharides -- 9.3.1 Synthesis of HS Oligosaccharide Library and a New Antithrombin-binding Octasaccharide -- 9.3.2 HS Microarray to Target HS and Protein Interaction -- 9.3.3 Design of Heparin Drugs -- 9.3.4 Scale-up Synthesis of HS 12-mer -- 9.4 Conclusion -- References -- Chapter 10 - Synthesis of Glycosphingolipids (GSLs) -- 10.1 Introduction -- 10.2 Chemical Strategies for Synthesizing Glycosphingolipids -- 10.2.1 Synthesis Using Glycosyl Trichloroacetimidate Donors -- 10.2.2 Synthesis with Glycosyl N-Phenyl Trifluoroacetimidates -- 10.2.3 Synthesis Using Glycosyl Fluoride Donors -- 10.2.4 Synthesis Using Koenigs-Knorr Glycosylation Reactions -- 10.2.5 Synthesis Using Thioglycoside Glycosyl Donors -- 10.2.6 Synthesis Using α-GlycosylIodide Donors -- 10.2.7 Synthesis Using Glycosyl Mesylate Donors -- 10.2.8 Synthesis Using Glycal Donors -- 10.2.9 Synthesis of α-Galactosylceramide Analogs from Naturally Configured α-Galactosides -- 10.3 Chemoenzymatic Synthesis of GSLs -- 10.3.1 Endoglycoceramidase-derived Glycosynthase-catalyzed Synthesis.
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10.3.2 Enzymatic Synthesis of Gb3 and iGb3 Using Lactosyl Ceramide as Acceptor Substrate -- 10.3.3 Enzymatic Assembly of Oligosaccharides Followed by Chemical Glycosylation -- 10.3.4 Enzymatic Sialylation of Glycolipids -- 10.3.5 One-pot Multienzyme (OPME) Chemoenzymatic Strategies -- 10.4 Conclusion -- Acknowledgement -- References -- Chapter 11 - Enzymatic and Chemoenzymatic Synthesis of Human Milk Oligosaccharides (HMOS) -- 11.1 Introduction -- 11.2 Bacterial and Mammalian Glycosyltransferases (GTs) that Have Been Used for the Synthesis of HMOS -- 11.3 Synthesis of HMOS via One-pot Multienzyme(OPME) Approaches -- 11.3.1 One-potMultienzyme (OPME) Glycosylation Systems -- 11.3.2 OPME Synthesis of Core Glycans LNTri II (Lc3) and LNnT -- 11.3.3 OPME Enzymatic Synthesis of Fucose-containing HMOS -- 11.3.3.1 OPME Synthesis of LNFP I -- 11.3.3.2 OPME Synthesis of LNFP III -- 11.3.3.3 OPME Synthesis of 3- FL, LNFP III, LNDFH II, and LNDFH III -- 11.3.4 OPME Synthesis of Sialylated HMOS -- 11.3.4.1 OPME Synthesis of 3′-SLand 6′-SL -- 11.3.4.2 OPME Synthesis of LST a, LST d, Sialylated LNFP III -- 11.3.4.3 OPME Synthesis of LSTc -- 11.3.4.4 OPME Synthesis of Disialylated HMOS -- 11.4 Glycosyltransferase-catalyzed Enzymatic Synthesis of HMOS -- 11.5 Enzymatic Synthesis of HMOS Using Transglycosidases, Glycosidases and Mutants -- 11.6 Chemoenzymatic Synthesis of HMOS -- 11.7 Whole-cell Production and Fermentation of Engineered E. coli Cells -- 11.8 Conclusion -- Acknowledgement -- References -- Chapter 12 - Synthesis of Marine Polysaccharides/Oligosaccharides and Their Derivatives -- 12.1 Introduction -- 12.2 Synthesis of Marine Polysaccharides -- 12.2.1 Biosynthesis of Marine Polysaccharides -- 12.2.2 Semi-synthesisof Marine-derived Polysaccharides -- 12.2.3 Synthesis of Glycopolymers and Glycoclusters to Mimic Natural Marine Polysaccharides.
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12.2.4 Synthesis and Modification of Marine Polysaccharide Derivatives.
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