102. Carbohydrates: The Essential Molecules Of Life

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102. Carbohydrates: The Essential Molecules Of Life

 

 

CATEGORY: Diet Nutrition Supplementation – 500 Courses

COURSE NUMBER: 102

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Syllabus

Preface and Acknowledgements xvii
Abbreviations xix
CHAPTER 1: The ‘Nuts and Bolts’ of Carbohydrates 1
The Early Years 1
The Constitution of Glucose and Other Sugars 7
The Cyclic Forms of Sugars, and Mutarotation 15
The Shape (Conformation) of Cyclic Sugars,
and the Anomeric Effect 23
References 32
CHAPTER 2: Synthesis and Protecting Groups 35
Esters 36
Acetates 36
Benzoates 38
Chloroacetates 39
Pivalates 39
Levulinates 39
Carbonates, borates, phosphates, sulfates and nitrates 40
Sulfonates 41
Ethers 42
Methyl ethers 42
Benzyl ethers 43
4-Methoxybenzyl ethers 44
Allyl ethers 45
Trityl ethers 45
Silyl ethers 45
Acetals 47
Cyclic acetals 49

Benzylidene acetals 50
4-Methoxybenzylidene acetals 53
Isopropylidene acetals 54
Diacetals 57
Cyclohexylidene acetals 58
Dithioacetals 58
Thioacetals 58
Stannylene acetals 59
The Protection of Amines 61
Orthogonality 66
References 67

CHAPTER 3: The Reactions of Monosaccharides 75
Oxidation 75
Reduction 80
Halogenation 84
Non-anomeric halogenation 85
Anomeric halogenation 89
Alkenes and Carbocycles 93
Non-anomeric alkenes 93
Anomeric alkenes 94
Carbocycles 96
Anhydro Sugars 98
Non-anomeric anhydro sugars 99
Anomeric anhydro sugars 101
Deoxy, Amino Deoxy and Branched-chain Sugars 105
Deoxy sugars 105
Amino deoxy sugars 107
Branched-chain sugars 111
Miscellaneous Reactions 112
Wittig reaction 112
Thiazole-based homologation 113
Mitsunobu reaction 114
Orthoesters 115

Industrially Important Ketoses 117
D-Fructose 117
L-Sorbose 119
Isomaltulose 119
Lactulose 120
Aza and Imino Sugars 121
References 124

CHAPTER 4: Formation of the Glycosidic Linkage 133
General 135
The different glycosidic linkages 135
The mechanism of glycosidation 136
Ion pairs and the solvent 136
The substituent at C2 137
The ‘armed/disarmed’ concept 137
The ‘torsional control’ concept 138
The ‘latent/active’ concept 139
Activation of the glycosyl acceptor 139
The concept of ‘orthogonality’ 140
‘Reciprocal donor/acceptor selectivity’ 140
Hemiacetals 141
Glycosyl Esters 144
Glycosyl Halides and Orthoesters 145
The Koenigs–Knorr reaction (1,2-trans) 146
The orthoester procedure (1,2-trans) 148
Halide catalysis (1,2-cis) 150
Glycosyl fluorides (1,2-cis and 1,2-trans) 152
Glycosyl Imidates (1,2-cis and 1,2-trans) 153
Thioglycosides (1,2-cis and 1,2-trans) 156
Seleno- and Telluroglycosides 160
Glycosyl Sulfoxides (sulfinyl glycosides; 1,2-cis and 1,2-trans) 162
Glycals 164
4-Pentenyl Activation (1,2-cis and 1,2-trans) 166

b-D-Mannopyranosides (1,2-cis) 169
Glycosyl halides 169
Glycosyl sulfoxides (and thioglycosides) 170
b-D-Glucopyranoside to b-D-mannopyranoside 171
Intramolecular aglycon delivery 172
Other methods 173
b-Rhamnopyranosides (1,2-cis) 174
2-Acetamido-2-deoxy Glycosides 174
2-Deoxy Glycosides 178
Sialosides 180
Furanosides 181
Miscellaneous Methods 182
Alkenyl glycosides 182
Remote activation 183
C-Glycosides 186
The addition of carbanions to anomeric electrophiles 187
The addition of electrophiles to anomeric carbanions 188
Glycosyl radicals 190
Miscellaneous 191
References 191
CHAPTER 5: Oligosaccharide Synthesis 203
Strategies in Oligosaccharide Synthesis 203
Linear syntheses 204
Convergent syntheses 206
Two-directional syntheses 206
‘One-pot’ syntheses 207
Polymer-supported Synthesis 210
Types of polymers 211
Linkers 212
Attachment of the sugar to the linker/polymer 213
The glycosyl donors used 213
Insoluble versus soluble polymers 213
Trichloroacetimidates 214
Pentenyl glycosides 215

Glycosyl sulfoxides 215
Thioglycosides 216
Glycals 216
Automated oligosaccharide synthesis 217
Combinatorial synthesis and the generation of ‘libraries’ 217
References 219

CHAPTER 6: Monosaccharide Metabolism 225
The Role of Charged Intermediates in Basic Metabolism 225
Glucose-6-phosphate: a Central Molecule in Carbohydrate Metabolism 226
Glycolysis 227
The Fate of Pyruvate in Primary Metabolism 230
Under aerobic conditions 230
Under anaerobic conditions 230
Gluconeogenesis 231
The Pentose Phosphate Pathway 232
The Glyoxylate Cycle 234
Biosynthesis of Sugar Nucleoside Diphosphates 235
Nucleotidylyltransferases 235
Biosynthesis of UDP-glucose, UDP-galactose and galactose 236
Biosynthesis of UDP-glucuronic acid and UDP-xylose 238
Biosynthesis of GDP-mannose 239
Biosynthesis of UDP-N-acetylglucosamine and
UDP-N-acetylgalactosamine 240
Biosynthesis of UDP-N-acetylmuramic acid 242
Biosynthesis of GDP-fucose 242
Biosynthesis of furanosyl nucleoside diphosphates:
UDP-galactofuranose and UDP-arabinofuranose 243
Biosynthesis of Sialic Acids and CMP-Sialic Acids 244
Biosynthesis of myo-Inositol 246
Biosynthesis of L-Ascorbic Acid 247
References 249

CHAPTER 7: Enzymatic Cleavage of Glycosides: Mechanism,

Inhibition and Synthetic Applications 253
Glycoside Hydrolases 253
Retaining and Inverting Mechanisms 255
Sequence-based classification of glycoside hydrolases 255
Mechanism of inverting glycoside hydrolases 256
Mechanism of retaining glycoside hydrolases that use
carboxylic acids as nucleophiles 256
Mechanism of retaining glycoside hydrolases that use tyrosine
as a catalytic nucleophile 258
Mechanism of retaining glycoside hydrolases that use
substrate-assisted catalysis 258
Unusual Enzymes that Catalyse Glycoside Cleavage 259
Transglycosidases 262
Structure-based Studies of Glycoside Hydrolases 263
Reagents and Tools for the Study of Glycoside Hydrolases 265
Non-covalent Glycoside Hydrolase Inhibitors 268
Exploitation of Glycoside Hydrolases in Synthesis 272
Thermodynamic control (reversed hydrolysis) 273
Kinetic control (transglycosidation) 273
Glycosynthases: Mutant Glycosidases for Glycoside Synthesis 276
Thioglycoligases: Mutant Glycosidases for Thioglycoside Synthesis 278
Hehre Resynthesis/Hydrolysis Mechanism 279
References 280
CHAPTER 8: Glycosyltransferases 285
Classification and Mechanism 285
Classification 286
Mechanism 286
Glycosyltransferases and the ‘One-enzyme One-linkage’
Hypothesis 291
Sequence-based Classification and Structure 292
Reversibility of Glycosyl Transfer by Glycosyltransferases 293

Inhibitors of Glycosyltransferases 294
‘Direct’ inhibition of glycosyltransferases 294
Therapeutically-useful glycosyltransferase inhibitors 299
‘Indirect’ inhibition of glycosyltransferases by metabolic
interference 301
Chemical Modification of Glycoconjugates Using Metabolic
Pathway Promiscuity 303
Use of Glycosyltransferases in Synthesis 305
Enzymatic synthesis using glycosyltransferases and sugar
(di)phosphonucleoside donors 306
Multienzyme systems including sugar (di)phosphonucleoside
generation and recycling 311
Synthesis using glycosyltransferases in engineered whole cell
systems 314
References 316
CHAPTER 9: Disaccharides, Oligosaccharides and Polysaccharides 321
Cellulose and Cellobiose 321
Starch, Amylopectin, Amylose and Maltose 324
Glycogen 326
Cyclodextrins 327
Sucrose, Sucrose Analogues and Sucrose Oligosaccharides 328
Lactose and Milk Oligosaccharides 331
Fructans 333
Chitin and Chitosan 334
Trehalose and Trehalose Oligosaccharides 335
1,3-b-Glucans 337
Mannans 338
References 339
CHAPTER 10: Modifications of Glycans and Glycoconjugates 343
Epimerization 344
Sulfation 345

Sulfotransferases 345
Sulfatases 345
Sulfated glycosaminoglycans 346
Heparin 347
Nodulation factors 349
Sulfated carbohydrates from halophilic bacteria 349
Mycobacterial sulfoglycolipids 350
Sulfated nucleosides 351
Sulfation in inflammation 351
Sulfatide and seminolipid 352
Phosphorylation 353
Mannose-6-phosphate 353
Phosphoglycosylation in Leishmania and other protists 354
Teichoic acids 355
Other phosphoglycans 356
Carboxylic Acid Esters 357
Acylated bacterial antigens 357
Mycobacterial fatty acid esters 359
Carboxylic acid esters in hemicelluloses 360
Modifications of Sialic Acids 362
Other Carbohydrate Modifications 363
References 364

CHAPTER 11: Glycoproteins and Proteoglycans 369
N-Linked Glycosylation 370
Biosynthesis of the lipid-linked oligosaccharide 371
Transfer of the lipid-linked oligosaccharide 372
N-Glycan trimming and the calnexin/calreticulin cycle 373
Golgi processing of N-linked glycans 374
ER-associated protein degradation 375
Diversity of N-linked glycans 376
Inhibitors of N-linked glycoprotein biosynthesis 377
Modification of N-Linked Glycans for Lysosomal Targeting 378
O-Linked Mucins/Proteoglycans, Blood Group Antigens and
Xenorejection 379
‘Mucin-type’ O-linked glycosylation 379

The blood group antigens 382
Xenotransplantation and the a-1,3-Gal epitope 386
O-Linked N-Acetyl-b-D-glucosamine 387
Glycosylphosphatidylinositol Membrane Anchors 389
Other Types of Protein Glycosylation 392
O-Fucose 392
C-Mannose 393
O-Mannose glycans 393
Rare protein modifications 394
Proteoglycans and Glycosaminoglycans 395
Hyaluronan 396
Chondroitin sulfate/dermatan sulfate 397
Keratan sulfate 398
Heparin and heparan sulfate 399
Lysosomal Degradation of Glycoconjugates 402
N-Linked glycoprotein degradation 403
Glycosaminoglycan degradation 404
Treatment of lysosomal storage disorders with imino sugar inhibitors 408
References 410

CHAPTER 12: Classics in Carbohydrate Chemistry and Glycobiology 413
The Immucillins: Transition-state Analogue Inhibitors of Enzymic
N-Ribosyl Transfer Reactions 413
Development of a Candidate Anti-toxic Malarial Vaccine 422
Synthetic Carbohydrate Anti-tumour Vaccines 428
New and Improved Anticoagulant Therapeutics Based on Heparin 435
References 442

APPENDIX I 445
Reagents for O-Protecting Group Removal 445
Reagents for N-Protecting Group Removal 446

APPENDIX II 447
Carbohydrate Nomenclature 447
The Literature of Carbohydrates 447
Reference literature 447
Primary literature 448
Monographs and related works 448
Recent edited works 449
Recent textbooks 450
Miscellaneous 451
EPILOGUE 453
INDEX 461

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