Carbohydrates: The Essential Molecules of Life
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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.
Key Features
* includes perspective from new co-author Spencer Williams, who enhances coverage of the connection between carbohydrates and life
* describes the basic chemistry and biology of carbohydrates
* reviews the concepts, synthesis, reactions, and biology of carbohydrates
* describes the basic chemistry and biology of carbohydrates
* reviews the concepts, synthesis, reactions, and biology of carbohydrates
Readership
Researchers, scientists, and advanced undergraduate and graduate students in biochemistry and organic chemistry.
Table of 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
Product details
- No. of pages: 496
- Language: English
- Copyright: © Elsevier Science 2008
- Published: October 24, 2008
- Imprint: Elsevier Science
- Hardcover ISBN: 9780240521183
- eBook ISBN: 9780080927022
About the Authors
Robert Stick
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).
Affiliations and Expertise
The University of Western Australia, Nedlands
Spencer Williams
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