Carbohydrates: the essential molecules of life
Gespeichert in:
| Beteiligte Personen: | , |
|---|---|
| Format: | Buch |
| Sprache: | Englisch |
| Veröffentlicht: |
Amsterdam [u.a.]
Elsevier Science
2009
|
| Ausgabe: | 2. ed. |
| Schlagwörter: | |
| Links: | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016769146&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| Abstract: | This book provides the "nuts and bolts" background for a successful study of carbohydrates - the essential molecules that not only give you energy, but are an integral part of many biological processes. A question often asked is 'Why do carbohydrate chemistry?' The answer is simple: It is fundamental to a study of biology. Carbohydrates are the building blocks of life and enable biological processes to take place. Therefore the book will provide a taste for the subject of glycobiology. |
| Beschreibung: | Previous ed.: San Diego, Calif.; London: Academic, 2001 |
| Umfang: | XXI, 474 S. 24cm |
| ISBN: | 0240521188 9780240521183 |
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| 245 | 1 | 0 | |a Carbohydrates |b the essential molecules of life |c Robert V. Stick ; Spencer J. Williams |
| 250 | |a 2. ed. | ||
| 264 | 1 | |a Amsterdam [u.a.] |b Elsevier Science |c 2009 | |
| 300 | |a XXI, 474 S. |c 24cm | ||
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| 500 | |a Previous ed.: San Diego, Calif.; London: Academic, 2001 | ||
| 520 | 3 | |a This book provides the "nuts and bolts" background for a successful study of carbohydrates - the essential molecules that not only give you energy, but are an integral part of many biological processes. A question often asked is 'Why do carbohydrate chemistry?' The answer is simple: It is fundamental to a study of biology. Carbohydrates are the building blocks of life and enable biological processes to take place. Therefore the book will provide a taste for the subject of glycobiology. | |
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Datensatz im Suchindex
| DE-BY-TUM_call_number | 0302 CHE 850f 2009 A 9367(2) |
|---|---|
| DE-BY-TUM_katkey | 1710153 |
| DE-BY-TUM_location | 03 |
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| _version_ | 1821933772436668416 |
| adam_text | Contents
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
Acetáis
47
Cyclic
acetáis
49
viii Contents
Benzylidene
acetáis
50
4-Methoxybenzylidene
acetáis
53
Isopropylidene
acetáis
54
Diacetals 57
Cyclohexylidene
acetáis
58
Dithioacetals 58
Thioacetals 58
Stannylene
acetáis
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
Contents ix
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
torsionai
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
(1,2475
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
χ
Contents
ß-D-Mannopyranosides
(1,2-cií)
169
Glycosyl
halides
169
Glycosyl
sulf
oxides
(and thioglycosides)
170
ß-D-Glucopyranoside
to
ß-D-mannopyranoside 171
Intramolecular aglycon delivery
172
Other methods
173
ß-Rhamnopyranosides
(1,2-rá)
174
г-Асеіатіао^^еоху
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
Contents
xi
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-ó-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-TV-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 »ryo-Inositol
246
Biosynthesis of L-Ascorbic Acid
247
References
249
xii Contents
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
Contents xiii
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-ß-Glucans 337
Mannans
338
References
339
CHAPTER
10:
Modifications of Glycans and Glycoconjugates
343
Epimerization
344
Sulfation 345
xiv Contents
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
О
-Linked Mucins/Proteoglycans, Blood Group Antigens and
Xenorejection
379
Mucin-type
О
-linked glycosylation
379
Contents xv
The blood group antigens
382
Xenotransplantation and the a-l^-Gal epitope
386
О
-Linked
N-Acetyl-ß-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
neparan 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
Enzymie
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
xvi Contents
APPENDIX
Π
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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| record_format | marc |
| spellingShingle | Stick, Robert V. Williams, Spencer J. Carbohydrates the essential molecules of life Carbohydrates Chemie (DE-588)4009816-3 gnd Kohlenhydratstoffwechsel (DE-588)4031656-7 gnd Kohlenhydrate (DE-588)4164517-0 gnd |
| subject_GND | (DE-588)4009816-3 (DE-588)4031656-7 (DE-588)4164517-0 |
| title | Carbohydrates the essential molecules of life |
| title_auth | Carbohydrates the essential molecules of life |
| title_exact_search | Carbohydrates the essential molecules of life |
| title_full | Carbohydrates the essential molecules of life Robert V. Stick ; Spencer J. Williams |
| title_fullStr | Carbohydrates the essential molecules of life Robert V. Stick ; Spencer J. Williams |
| title_full_unstemmed | Carbohydrates the essential molecules of life Robert V. Stick ; Spencer J. Williams |
| title_short | Carbohydrates |
| title_sort | carbohydrates the essential molecules of life |
| title_sub | the essential molecules of life |
| topic | Carbohydrates Chemie (DE-588)4009816-3 gnd Kohlenhydratstoffwechsel (DE-588)4031656-7 gnd Kohlenhydrate (DE-588)4164517-0 gnd |
| topic_facet | Carbohydrates Chemie Kohlenhydratstoffwechsel Kohlenhydrate |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016769146&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT stickrobertv carbohydratestheessentialmoleculesoflife AT williamsspencerj carbohydratestheessentialmoleculesoflife |
Inhaltsverzeichnis
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Teilbibliothek Chemie
| Signatur: |
0302 CHE 850f 2009 A 9367(2) Lageplan |
|---|---|
| Exemplar 1 | Ausleihbar Am Standort |