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By Robert Stick, The University of Western Australia, Nedlands Spencer Williams
Description 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.
Covering the basics of carbohydrates and then the
chemistry and reactions of carbohydrates this book will enable a chemist to gain essential knowledge that will enable them to move smoothly
into the worlds of biochemistry, molecular biology and cell biology.
Audience
Researchers, scientists, and advanced undergraduate and graduate students in biochemistry and organic chemistry.
Contents Contents
Preface and Acknowledgements
Abbreviations
CHAPTER 1: The ?Nuts and Bolts' of Carbohydrates
The early years
The constitution
of glucose and other sugars
The cyclic forms of sugars, and mutarotation
The shape (conformation) of cyclic sugars, and the anomeric
effect
References
CHAPTER 2: Synthesis and Protecting Groups
Esters
Ethers
Acetals
The protection of amines
Orthogonality
References
CHAPTER 3: The Reactions of Monosaccharides
Oxidation
Reduction
Halogenation
Alkenes and carbocycles
Anhydro sugars
Deoxy, amino
deoxy and branched-chain sugars
Miscellaneous reactions
Industrially important ketoses
Aza and imino sugars
References
CHAPTER 4:
The Formation of the Glycosidic Linkage
General
Hemiacetals
Glycosyl esters
Glycosyl halides and orthoesters
Glycosyl imidates
Thioglycosides
Glycosyl sulfoxides
Glycals
4-Pentenyl activation
Beta-D-Mannopyranosides
2-Acetamido-2-deoxy glycosides
2-Deoxy
glycosides
Sialosides
Furanosides
Miscellaneous methods
C-Glycosides
References
CHAPTER 5: Oligosaccharide Synthesis
Strategies
in oligosaccharide synthesis
Polymer-supported synthesis of oligosaccharides
References
CHAPTER 6: Monosaccharide Metabolism
Glucose-6-phosphate:
a central molecule in carbohydrate metabolism
Glycolysis
The fate of pyruvate in primary metabolism
Gluconeogenesis
The pentose phosphate
pathway
The glyoxylate cycle
Biosynthesis of sugar nucleoside diphosphates
Biosynthesis of sialic acids and CMP-sialic acids
Biosynthesis
of myo-inositol
Biosynthesis of L-ascorbic acid
References
CHAPTER 7: Enzymatic Cleavage of Glycosides: Mechanism, Inhibition and Synthetic
Applications
Glycoside hydrolases
Retaining and inverting mechanisms
Unusual enzymes that catalyze glycoside cleavage
Transglycosidases
Structural-based studies of glycoside hydrolases
Reagents and tools for the study of glycoside hydrolases
Non-covalent glycoside hydrolase
inhibitors
Exploitation of glycoside hydrolases in synthesis
Glycosynthases: mutant glycosidases for glycoside synthesis
Thioglycoligases:
mutant glycosidases for thioglycoside synthesis
Hehre resynthesis/hydrolysis mechanism
References
CHAPTER 8: Glycosyltransferases
Classification and mechanism
Reversibility of glycosyl transfer by glycosyltransferases
Inhibitors of glycosyltransferases
?Direct'
inhibition of glycosyltransferases
Therapeutically-useful glycosyltransferase inhibitors
?Indirect' inhibition of glycosyltransferases
by metabolic interference
Chemical modification of glycoconjugates using metabolic pathway promiscuity
Exploitation of glycosyltransferases
in synthesis
References
CHAPTER 9: Disaccharides, Oligosaccharides and Polysaccharides
Cellobiose and cellulose
Starch, amylopectin,
beta-amylose and maltose
Glycogen
Cyclodextrins
Sucrose, sucrose analogues and sucrose oligosaccharides
Lactose and milk oligosaccharides
Fructans
Chitobiose, chitin and chitosan
Trehalose and trehalose oligosaccharides
1,3-beta-Glucans
Mannans
References
CHAPTER 10:
Modifications of Glycans and Glycoconjugates
Epimerization
Sulfation
Phosphorylation
Acylation
Modifications of sialic acids
Other
carbohydrate modifications
References
CHAPTER 11: Glycoproteins and Proteoglycans
N-Linked Glycosylation
Modification of N-linked
glycans for lysosomal targeting
O-Linked mucins/proteoglycans, blood group antigens and xenorejection
O-Linked N-acetyl-beta-D-glucosamine
Glycosylphosphatidylinositol (GPI) membrane anchors
Other types of protein glycosylation
Proteoglycans and glycosaminoglycans
Lysosomal
degradation of glycoconjugates
References
CHAPTER 12: Classics in Carbohydrate Chemistry and Glycobiology
The immucillins: transition
state analogue inhibitors of enzymic N-ribosyl transfer reactions
Development of a candidate anti-toxic malarial vaccine
Synthetic
carbohydrate anti-tumour vaccines
New and improved anticoagulant therapeutics based on heparin
EPILOGUE
APPENDIX I
Protecting groups
APPENDIX II
Carbohydrate nomenclature
The literature of carbohydrates
Reference literature
Primary literature
Monographs and
related works
Recent edited works
Recent textbooks
Miscellaneous
INDEX OF AUTHORS CITED IN THE REFERENCES
GENERAL SUBJECT INDEX
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