Carbohydrates: The Sweet Molecules of Life

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Academic Press, 2001 - Science - 256 pages
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This book is on carbohydrates-the essential molecules that give you energy. They are the building blocks of life. This book delivers up-to-date coverage on all aspects of carbohydrate chemistry. The molecules are sometimes sugars, i.e. "sweet," hence the subtitle "The Sweet Molecules of Life."

Carbohydrates first gives the "nuts and bolts" of carbohydrate chemistry, enabling the reader to appreciate the subsequent chapters on protecting groups and the reactions of monosaccharides. (The protecting groups do just that-they are put on the molecules as a temporary measure during one or more reactions to stop the wrong bit of the molecule being changed during that reaction.)

* Introduces the basic chemistry of carbohydrates
* Describes the concepts, protecting groups, and reactions of carbohydrates
* Includes all aspects of the synthesis of the glycosidic linkage
* Gives an introduction to glycobiology and vaccines
* Includes references to carbohydrate literature
 

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Contents

The Meaning of Life
1
The Early Years
3
References
8
Grandfather Glucose
9
References
18
Heidi und Heinz
19
References
26
The Shape of Things to Come
27
Thioglycosides 12cs and 12frans
137
Seleno and Telluroglycosides
141
Glycosyl Sulfoxides sulfinyl glycosides 12cis and 12trans
142
References
145
Glycals and 4Pentenyl Glycosides 12cs and 12trans
146
4Pentenyl Glycosides
148
References
151
BDMannopyranosides 12cis
152

References
34
Synthesis and Protecting Groups
37
References
38
Ethers44
43
References
46
Acetßis
49
Cyclic Acetals
50
Dithioacetals
58
Stannylene Acetais
59
References
61
Amines
63
References
65
The Reactions of Monosaccharides
67
Reduction
72
References
75
Halogenation
77
Nonanomeric Halogenation
78
Anomeric Halogenation
81
References
85
Alkenes and Carbocycles
86
Carbocycles
89
References
92
Anhydro Sugars
93
Anomeric Anhydro Sugars
95
References
99
Deoxy Amino Deoxy and Branchedchain Sugars
100
Ammo Deoxy Sugars
102
Branchedchain Sugars
105
References
106
Miscellaneous Reactions
107
Thiazolebased Homologation
108
Orthoesters
110
Olefin Metathesis
111
The Formation of the Glycosidic Linkage
113
The Different Glycosidic Linkages
115
Ionpairs and Solvent
116
The Substituent at C2
117
The Torsional Control Concept
118
Activation of the Glycosyl Acceptor
119
References
122
Glycosyl Halides
124
The Orthoester Procedure 12frans
127
Halide Catalysis 12cis
129
Glycosyl Fluorides 12cs and 12trans
131
References
132
The Trichloroacetimidate Method 12cis and 12trans
133
References
136
Glycosyl Sulfoxides
153
▀DGlucopyranoside to ▀oMannopyranoside
154
Intramolecular Aglycon Delivery
156
Other Methods
157
References
158
CGlycosides
164
References
169
2Acetamido2Deoxy and 2Deoxy Glycosides
171
2Deoxy Glycosides
174
References
177
Oligosaccharide Synthesis
179
Linear Syntheses
180
Convergent Syntheses
182
Twodirectional Syntheses
183
References
185
Types of Polymers
186
Linkers
187
Insoluble versus Soluble Polymers
188
Combinatorial Synthesis and the Generation of Libraries
192
References
194
Enzymecatalysed Glycoside Synthesis
196
Glycoside Hydrolases Glycosidases
198
Other Matters
208
References
209
Disaccharides Oligosaccharides and Polysaccharides
213
Nonreducing Disaccharides
215
Oligosaccharides
216
Polysaccharides
217
Glycogen
218
Chitin
219
Heparin
220
References
221
Glycoconjugates and Glycobiology Glycoconjugates
223
Glycolipids
224
Lipopolysaccharides
225
Glycobiology
226
Sialyl Lewis
229
References
230
Carbohydratebased Vaccines
233
References
236
Appendix
239
Primary Literature
240
Recent Edited Works
241
Other Works
242
Index
245
Copyright

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About the author (2001)

Robert Stick is a Queenslander by birth and completed his undergraduate and higher degrees at the University of Queensland. Following post-doctoral studies with Ray Lemieux and Sir Derek Barton, he took a faculty position at The University of Western Australia in 1975 and has since spent sabbatical leaves with Bert Fraser-Reid (Duke University), and with Bill Cullen and Steve Withers (both of the University of British Columbia).

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