E-Book, Englisch, 422 Seiten, Format (B × H): 152 mm x 229 mm
Horton Advances in Carbohydrate Chemistry and Biochemistry
1. Auflage 2009
ISBN: 978-0-08-088598-8
Verlag: Academic Press
Format: EPUB
Kopierschutz: 6 - ePub Watermark
E-Book, Englisch, 422 Seiten, Format (B × H): 152 mm x 229 mm
ISBN: 978-0-08-088598-8
Verlag: Academic Press
Format: EPUB
Kopierschutz: 6 - ePub Watermark
Since its inception in 1945, this serial has provided critical and integrating articles written by research specialists that integrate industrial, analytical, and technological aspects of biochemistry, organic chemistry, and instrumentation methodology in the study of carbohydrates. The articles provide a definitive interpretation of the current status and future trends in carbohydrate chemistry and biochemistry.
Zielgruppe
Researchers in biochemistry, organic chemistry, medicinal chemistry and instrumentation methodology
Fachgebiete
Weitere Infos & Material
1;Front Cover;1
2;Advances in Carbohydrate Chemistry and Biochemistry;4
3;Copyright Page;5
4;Contents;6
5;List of Contributors;10
6;Preface;12
7;Chapter 1: Gerald Aspinall;18
7.1;Keynote Publications;24
8;Chapter 2: Vittorio Crescenzi;28
9;Chapter 3: Developments in the Karplus Equation as They Relate to the Nmr Coupling Constants Of Carbohydrates;32
9.1;I. Introduction;33
9.2;II. The Impact of Improved NMR Instrumentation;34
9.3;III. The Impact of Molecular Modeling;35
9.4;IV. Vicinal Coupling Constants;36
9.4.1;1. ProtonProton Couplings;36
9.4.2;2. ProtonCarbon Couplings;51
9.4.3;3. ProtonNitrogen Couplings;60
9.4.4;4. Phosphorus Couplings;62
9.4.5;5. CarbonCarbon Couplings;66
9.5;V. Other Types of Vicinal Couplings;75
9.5.1;1. Fluorine Couplings;75
9.5.2;2. CarbonTin Couplings;79
9.6;VI. Couplings Over Four Bonds;79
9.6.1;1. ProtonProton Couplings;79
9.7;VII. Couplings Over Five Bonds;83
9.7.1;1. ProtonProton Couplings;83
9.8;VIII. Online Calculators for Coupling Constants and Torsions;85
9.9;IX. Summary;87
9.10;References;88
10;Chapter 4: Computational Studies of the Role of Glycopyranosyl Oxacarbenium Ions in Glycobiology and Glycochemistry;98
10.1;I. Introduction;98
10.1.1;1. Importance of Glycopyranosyl Oxacarbenium Ions;98
10.2;II. Galactopyranosyl Oxacarbenium Ion as an Illustrative Model;99
10.2.1;1. Background;99
10.2.2;2. Isolated CationsRing and C5C6 SideChain Conformations;104
10.2.3;3. Facially Selective MethanolOxacarbenium Ion Complexes;113
10.2.4;4. The Orientations and Conformations of Side Chains at C2, C3, C4, and C5;124
10.2.5;5. The Role of C2O2 Rotations, Including NeighboringGroup Participation;133
10.2.6;6. The Role of Proton Transfer in the Transition State for Glycosylation Reactions;145
10.2.7;7. Differences in Ionization Between and Donors;151
10.3;III. Conclusions and Future Directions;155
10.3.1;1. Summary of Glycosylation Reaction Mechanisms;155
10.3.2;2. Further Calculations Based on Existing Methodology;160
10.3.3;3. Future Calculations Requiring Methodology Development;160
10.3.4;4. Experimental Studies of Glycosylation;161
10.4;Acknowledgments;162
10.5;References;162
11;Chapter 5: Oligosaccharide Synthesis: From Conventional Methods to Modern Expeditious Strategies;176
11.1;I. Introduction;177
11.2;II. Chemical Glycosylation and Conventional Oligosaccharide Synthesis;180
11.2.1;1. Principles of Chemical Glycosylation;180
11.2.2;2. Traditional Linear Oligosaccharide Synthesis;182
11.2.3;3. Convergent Block Synthesis;184
11.3;III. Selective (LeavingGroup Based) Strategies;192
11.3.1;1. Selective Activation;192
11.3.2;2. TwoStep Activation and the In situ Preactivation;197
11.3.3;3. ActiveLatent Strategy;200
11.3.4;4. Orthogonal and Semiorthogonal Strategies;203
11.3.5;5. Deactivation by Steric Hindrance;208
11.3.6;6. Temporary Deactivation Concept;208
11.4;IV. Chemoselective (ProtectingGroup Based) Strategies;211
11.4.1;1. Arming and Disarming with Neighboring Substituents;213
11.4.2;2. ReactivityBased Programmable Strategy;216
11.4.3;3. Disarming by the Remote Substituents;217
11.4.4;4. Disarming by Torsional Effects;218
11.4.5;5. SuperArmed Glycosyl Donors;221
11.5;V. RegioselectivityBased Strategies;223
11.5.1;1. Hydroxyl Reactivity;223
11.5.2;2. Triphenylmethyl Reactivity;225
11.5.3;3. Bidirectional Approaches;226
11.6;VI. Novel Technologies for the Rapid and HighThroughput Oligosaccharide Synthesis;228
11.6.1;1. OnePot Strategies;229
11.6.2;2. PolymerSupported, SolidPhase, and Automated Synthesis;234
11.6.3;3. Fluorous TagSupported and Microreactor Synthesis;241
11.7;VII. Enzymatic Approach;243
11.7.1;1. Oligosaccharide Synthesis with Glycosyltransferases;245
11.7.2;2. Oligosaccharide Synthesis with Glycosidases (Hydrolases);248
11.8;VIII. Outlook;249
11.9;References;251
12;Chapter 6: Stereocontrolled Synthesis of Mannans and Rhamnans;266
12.1;I. Introduction;266
12.2;II. The Mannans and Rhamnans;267
12.2.1;1. Mannan Synthesis in the Absence of NeighboringGroup Participation;267
12.2.2;2. Neighboring GroupDirected Mannan Synthesis;277
12.2.3;3. Synthesis of Rhamnans;296
12.3;III. The Mannans and Rhamnans;301
12.3.1;1. Introduction;301
12.3.2;2. Mannan Synthesis by Indirect Methods;301
12.3.3;3. Rhamnan Synthesis by Indirect Methods;306
12.3.4;4. Mannan Synthesis by Direct Methods;306
12.3.5;5. Rhamnan Synthesis by Direct Methods;314
12.4;References;316
13;Chapter 7: Glycobiology of Trypanosoma cruzi;326
13.1;I. Introduction;327
13.2;II. Life Cycle of the Parasite;327
13.3;III. Specific CellSurface Glycoconjugates;328
13.3.1;1. Glycoinositolphospholipids, Free and as Anchors of Proteins;328
13.3.1.1;a. Glycoinositolphospholipids;328
13.3.1.2;b. GIPL Anchors (GPIs) in T. cruzi Glycoproteins;330
13.3.1.3;c. Biological and Immunological Properties of T. cruzi GIPLs;333
13.3.1.4;d. Biosynthesis of T. cruzi GIPLs;334
13.3.1.5;e. Chemical Synthesis of the T. cruzi GIPLs;336
13.3.2;2. Trypanosoma cruzi Mucins;336
13.3.3;3. T. cruzi Transsialidase (TcTS);351
13.3.4;4. Other Glycoproteins;367
13.4;IV. Concluding Remarks;369
13.5;References;370
14;Author Index;382
15;Subject Index;408
16;Color Plates;426
