Carbohydrates: The Essential Molecules of Life

Carbohydrates: The Essential Molecules of Life

2nd Edition - October 24, 2008

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  • Authors: Robert Stick, Spencer Williams
  • Hardcover ISBN: 9780240521183
  • eBook ISBN: 9780080927022

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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.

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

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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