Sialic Acids
Chemistry, Metabolism, and Function
(Sprache: Englisch)
Rapid progress in the field of sialic acids has made it desirable to collect the new data about these unique sugars and to continue the series of books on this topic. In 1960, A. GOTTSCHALK wrote "The Chemistry and Biology of Sialic Acids and Related...
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Klappentext zu „Sialic Acids “
Rapid progress in the field of sialic acids has made it desirable to collect the new data about these unique sugars and to continue the series of books on this topic. In 1960, A. GOTTSCHALK wrote "The Chemistry and Biology of Sialic Acids and Related Substances" (Cambridge University Press) and in 1976, A. ROSENBERG and C. -L. SCHENGRUND published "Biological Roles of Sialic Acids" (Plenum Press). In this book emphasis is given to various modern methods used in the isolation and analysis of sialic acids. New approaches to the synthesis of free and bound sialic acids are described and the vast field of occurrence and metabolism of these substances is reviewed. Sialidoses are dealt with in one of the chapters, because sialidases have been recognized as factors of pathophysiological im portance. As knowledge is increasing about the involvement of sialic acids in many aspects of cell biology, another chapter is devoted to these phenomena. With this book I intend to demonstrate modern trends in sialic acid chemistry and biochemistry, and I hope that it will be of practical use and find its place in laboratories rather than in libraries. This publication offers an opportunity to thank all colleagues in many countries, including my coworkers at the universities of Bochum and Kiel, for their cooperation, stimulating discussions and, very important, useful criticism. The continuous cooperation with J. F. G. VLIEGENTHART and his coworkers, Utrecht, has been rewarding in many respects.
Inhaltsverzeichnis zu „Sialic Acids “
A. IntroductionB. Occurrence of Sialic Acids
I. Introduction
II. Viruses
III. Bacteria
IV. Fungi, Algae, and Plants
V.Protozoa
VI. Porifera, Platyhelminthes, Nemertinea, Ctenophora, andCoelenterata
VII. Sipuncula, Annelida, Arthropoda, and Mollusca
VIII. Bryozoa, Brachiopoda, Chaetognatha, and Echinodermata
IX. Hemichordata, Urochordata, and Cephalochordata
X.Vertebrata
1. Pisces 13
2. Amphibia
3. Reptilia
4. Aves
5. Mammalia
a) Introduction
b) Oligosaccharides
- Milk and Colostrum
- Urine
- Nucleotide Sugars
c) Glycoproteins
- Serum
- Epithelial or Mucus Glycoproteins
- Membrane Glycoproteins
- Brain Glycoproteins
- Milk, Colostrum and Urine Glycoproteins and Glycopeptides
- Hormone and Enzyme Glycoproteins
- Lipoproteins
- Miscellaneous
d) Gangliosides
XI. The Nature of Sialic Acids
1. Introduction
2. Free Sialic Acids
3. Glycosidically Linked Sialic Acids
a) The Type of Sialic Acid
b) Sialyloligosaccharide Structural Considerations
- Terminal Linear Position
- Terminal "Side-Chain Position"
- Internal Sialic Acids in OUgosialylglycoconjugates and Sialylpoly- saccharides
- Internal Sialic Acids in the Echinodermata
XII. Evolution of the Sialic Acids
- Biblography
C. Isolation and Purification of Sialic Acids
I. Introduction
II. Acid Hydrolysis
III. Enzymic Hydrolysis
IV. Lipid Extraction
V. Ion-Exchange Chromatography
VI. Cellulose Chromatography
VII. Crystallization
VIII. Other Methods
D. Synthesis of Sialic Acids and Sialic Acid Derivatives
I.Introduction
II. Glycosides of Sialic Acids
III. Sialodisaccharides
IV. 2-Deoxy-2,3-dehydro-N-acylneuraminic Acids
V. Methylated Sialic Acids
VI. Isotopically Labelled Sialic Acids
VII. Substrates for Sialidase Investigations
VIII. C7- and C8-Analogues of Sialic Acids
IX. Miscellaneous Sialic Acids and Sialic Acid Derivatives
E. Colorimetry and Thin-Layer Chromatography of Sialic Acids
I. Introduction
II. Colorimetry and Fluorimetry
1. Diphenol Reagent
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Assays
a) Orcinol
b) Resorcinol
- Resorcinol/Cu2+ Assay
- Periodate/Resorcinol/Cu2+ Assay
2. Periodic Acid/Thiobarbituric Acid Assays
a) The Warren and Aminoff Methods
b) Interference
3. Periodic Acid/Methyl-3-Benzothiazolinone-2-Hydrazone Method
4. Fluorimetrie Assays
5. Enzymic Assays
6. O-Acyl Group Assay
7. Automatic Procedures
8. High Performance Liquid Chromatography
9. Other Methods
10. Quantitative Problems in Sialic Acid Release
III. Thin-Layer Chromatography
1. Chromatographic Systems
2. Visualization
3. Two-Dimensional Techniques
a) Individual Sialic Acid Determination
b) 0-Acyl Group Identification
c) Sialic Acid Identification in Oligosaccharides
4. Paper Chromatography
F. Gas-Liquid Chromatography and Mass Spectrometry of Sialic Acids
I. Introduction
II. Gas-Liquid Chromatography
1. Quantitative Sugar Analysis, Including Sialic Acid
2. Hydrolytic Release of Sialic Acids from Sialobiopolymers
3. Preparation and Analysis of Trimethylsilylated N,0-AcyNeuraminic Acid Methyl Esters
4. Preparation and Analysis of Pertrimethylsilylated N,0-Acylneuraminic Acids
5. Analysis of Acetyl and/or Glycolyl Residues of Sialic Acid
III. Gas-Liquid Chromatography/Mass Spectrometry
1. Mass Spectrometric Identification Procedure
2. Analysis of (0-Acylated) N-Acylneuraminic Acids Isolated from Biological Material
3. Sialic Acids and Methylation Analysis
4. Miscellaneous Sialic Acids and Sialic Acid Derivatives
5. Quantitative Analysis of Sialic Acids by g.l.c./m.s
6. Sialooligosaccharides, Sialoglycolipids, and Sialoglycopeptides
G. NMR Spectroscopy of Sialic Acids
I. Introduction
II. 1H-NMR Spectroscopy
1. N-Acetyl- and N-Glycolylneuraminic Acid
2. O-Acetylated Neuraminic Acid Derivatives
3. Analysis of Sialic Acid Linkage Types in Glycoconjugates
a) The Anomeric Configuration of Sialic Acid
b) Sialic Acid in Carbohydrate Chains of the N-Acetyllactosamine Type
c) Sialic Acid in 0-Glycosidically Linked Carbohydrate Chains
d) CMP-N-Acetylneuraminic Acid and Degradation Products
4. Enzymic and Chemical Conversions
5. Complexes of Sialic Acids with Ca2+
III. 13C-NMR Spectroscopy
1. N-Acetyl- and Glycolylneuraminic Acid
2. O-Acetylated Neuraminic Acid Derivatives
3. Polysaccharides
4. Esterified Polysaccharides
5. CMP-N-Acetylneuraminic Acid and 2-Deoxy-2,3-dehydro-N-acetylneuraminic Acid
6. Complexes of Sialic Acids with Ca2+
7. 13C-Relaxation Studies on Sialic Acids and Sialyllactoses
IV. Analytical Procedures
1. Instrumentation
2. Solutions
H. Histochemistry of Sialic Acids
I. Introduction
II. Histochemical Identification of Sialic Acids
1. General
2. Methods Based upon Staining with Cationic Dyes
a) Staining at Different pH's
b) Removal of Specific Components Contributing to the Staining
- Use of Enzymatic Procedures
- Use of Chemical Procedures
i) Acid Hydrolysis
- ii) Methylation
c) Inhibition of Staining with Alcian Blue in the Presence of Varying Concentrations of Inorganic Salts (C.E.C. Methods)
3. Methods Based upon the Use of Periodate Oxidation
a) The PAS Reaction
b) The Periodic Acid/Phenylhydrazine/Schiff (PAPS) Procedure
c) The Use of Very Dilute Periodic Acid
d) Identification of Side Chain O-Acylated Sialic Acid
- PBT/KOH/PAS Technique
- PAT/KOH/PAS Procedure
- 9-0-Acyl Sialic Acids
4. Methods Based upon the Use of Lectins
III. Staining and Control Procedures
1. Fixation and Processing
2. PAS Technique
3. PBT/KOH/PAS Technique
4. PAT/KOH/PAS Technique
5. High Iron Diamine/Alcian Blue Method
6. Alcian Blue (pH 2.5)
7. Alcian Blue (pH 1.0)
8. Neuraminidase Digestion
9. Acid Hydrolysis
- BibHography
I. Metabolism of Sialic Acids
I. Introduction
II. De novo Biosynthesis of Sialic Acids
1. Introduction
2. From Glucose to UDP-N-Acetylhexosamine
3. Formation of NeuSAc
4. Activation and Modification of Neu5Ac
III. Sialyltransfer
1. Introduction
2. Sialyltransfer in Cells and Cell-Free Systems: Cellular Location
a) Intact Cells
- N-Glycosidically Linked Oligosaccharide Chains
- O-Glycosidically Linked Oligosaccharides (Ser/Thr-GalNAc Type)
- Glycolipids (Gangliosides)
- Membrane Glycoconjugates
b) Cell-Free Systems
- N-Glycosidically Linked Oligosaccharide Chains
- O-Glycosidically Linked Oligosaccharide Chains
- Gang Hosides
- Membrane Glycoconjugates
3. Sialyltransferases with N-Glycosidically Linked Oligosaccharide Substrates
4. Sialyltransferases with 0-Glycosidically Linked Oligosaccharide Substrates
5. Sialyltransferases with Glycolipid Substrates
6. Sialyltransferases with Oligosaccharide Substrates
7. Sialyltransferases with Membrane Glycoprotein Substrates
8. Sialyltransferases in Bacterial Systems
9. Ectosialyltransferases
10. Soluble Serum Sialyltransferases
IV. Catabolism of Sialic Acids
1. Introduction
2. CMP-Sialic Acid Hydrolase
3. Sialidases
a) Anomeric Specificity
b) The Carboxyl Group
c) N-Substitution
d) O-Substitution
e) Length of the Side Chain
f) Side Chain or Branch Sialic Acids
g) Influence of Aglycone and Natural Glycosidic Binding Partners
h) Glycosidic Linkage
i) Molecular Parameters
j) Kinetic Parameters and pH Optima
k) Activators and Inhibitors
4. Acylneuraminate Pyruvate-Lyase
a) Bacteria
b) Mammals
V. Uptake and Recycling of Sialic Acids in Cells
VI. Regulation of Sialic Acid Metabolism
1. Introduction
2. Genetic Regulation
3. Regulation of Enzyme Activities
a) Specificity
b) Kinetic Effects
- Substrate and Enzyme Concentration
- Inhibition and Activation
c) Feedback Inhibition
d) Sialuria, a Defect in SiaUc Acid MetaboUsm
4. Nutritional Factors and Energy
5. Spatial Organization
6. Hormonal and Nervous Regulation
- Biblography
J. Biological Significance of Sialic Adds
I. Introduction
II. Role in Cellular Adhesiveness
1. Adhesiveness of Benign Cells
2. Adhesiveness of Transformed and Malignant Cells
III. Influence on the Life-Span of Blood Components
1. Erythrocytes
2. Thrombocytes
3. Lymphocytes
4. Serum Glycoconjugates
IV. Blood Clotting
V. Immunology and Infection
VI. Immunotherapy with Neuraminidase-Treated Cells
VII. Gang Hosides
VIII. Mucins of the Gastrointestinal Tract
IX. Hormones
X. Concluding Remarks and Outlook
- Biblography
K. Sialidoses
I. Introduction
II. Clinical Manifestations and Classification
III. The Metabolic Defect
1. Storage Material
2. The Neuraminidase Defect
3. Pathogenesis
IV. Other Disorders with Neuraminidase Deficiency
V. Laboratory Diagnosis
VI. Summary
- Biblography
a) Orcinol
b) Resorcinol
- Resorcinol/Cu2+ Assay
- Periodate/Resorcinol/Cu2+ Assay
2. Periodic Acid/Thiobarbituric Acid Assays
a) The Warren and Aminoff Methods
b) Interference
3. Periodic Acid/Methyl-3-Benzothiazolinone-2-Hydrazone Method
4. Fluorimetrie Assays
5. Enzymic Assays
6. O-Acyl Group Assay
7. Automatic Procedures
8. High Performance Liquid Chromatography
9. Other Methods
10. Quantitative Problems in Sialic Acid Release
III. Thin-Layer Chromatography
1. Chromatographic Systems
2. Visualization
3. Two-Dimensional Techniques
a) Individual Sialic Acid Determination
b) 0-Acyl Group Identification
c) Sialic Acid Identification in Oligosaccharides
4. Paper Chromatography
F. Gas-Liquid Chromatography and Mass Spectrometry of Sialic Acids
I. Introduction
II. Gas-Liquid Chromatography
1. Quantitative Sugar Analysis, Including Sialic Acid
2. Hydrolytic Release of Sialic Acids from Sialobiopolymers
3. Preparation and Analysis of Trimethylsilylated N,0-AcyNeuraminic Acid Methyl Esters
4. Preparation and Analysis of Pertrimethylsilylated N,0-Acylneuraminic Acids
5. Analysis of Acetyl and/or Glycolyl Residues of Sialic Acid
III. Gas-Liquid Chromatography/Mass Spectrometry
1. Mass Spectrometric Identification Procedure
2. Analysis of (0-Acylated) N-Acylneuraminic Acids Isolated from Biological Material
3. Sialic Acids and Methylation Analysis
4. Miscellaneous Sialic Acids and Sialic Acid Derivatives
5. Quantitative Analysis of Sialic Acids by g.l.c./m.s
6. Sialooligosaccharides, Sialoglycolipids, and Sialoglycopeptides
G. NMR Spectroscopy of Sialic Acids
I. Introduction
II. 1H-NMR Spectroscopy
1. N-Acetyl- and N-Glycolylneuraminic Acid
2. O-Acetylated Neuraminic Acid Derivatives
3. Analysis of Sialic Acid Linkage Types in Glycoconjugates
a) The Anomeric Configuration of Sialic Acid
b) Sialic Acid in Carbohydrate Chains of the N-Acetyllactosamine Type
c) Sialic Acid in 0-Glycosidically Linked Carbohydrate Chains
d) CMP-N-Acetylneuraminic Acid and Degradation Products
4. Enzymic and Chemical Conversions
5. Complexes of Sialic Acids with Ca2+
III. 13C-NMR Spectroscopy
1. N-Acetyl- and Glycolylneuraminic Acid
2. O-Acetylated Neuraminic Acid Derivatives
3. Polysaccharides
4. Esterified Polysaccharides
5. CMP-N-Acetylneuraminic Acid and 2-Deoxy-2,3-dehydro-N-acetylneuraminic Acid
6. Complexes of Sialic Acids with Ca2+
7. 13C-Relaxation Studies on Sialic Acids and Sialyllactoses
IV. Analytical Procedures
1. Instrumentation
2. Solutions
H. Histochemistry of Sialic Acids
I. Introduction
II. Histochemical Identification of Sialic Acids
1. General
2. Methods Based upon Staining with Cationic Dyes
a) Staining at Different pH's
b) Removal of Specific Components Contributing to the Staining
- Use of Enzymatic Procedures
- Use of Chemical Procedures
i) Acid Hydrolysis
- ii) Methylation
c) Inhibition of Staining with Alcian Blue in the Presence of Varying Concentrations of Inorganic Salts (C.E.C. Methods)
3. Methods Based upon the Use of Periodate Oxidation
a) The PAS Reaction
b) The Periodic Acid/Phenylhydrazine/Schiff (PAPS) Procedure
c) The Use of Very Dilute Periodic Acid
d) Identification of Side Chain O-Acylated Sialic Acid
- PBT/KOH/PAS Technique
- PAT/KOH/PAS Procedure
- 9-0-Acyl Sialic Acids
4. Methods Based upon the Use of Lectins
III. Staining and Control Procedures
1. Fixation and Processing
2. PAS Technique
3. PBT/KOH/PAS Technique
4. PAT/KOH/PAS Technique
5. High Iron Diamine/Alcian Blue Method
6. Alcian Blue (pH 2.5)
7. Alcian Blue (pH 1.0)
8. Neuraminidase Digestion
9. Acid Hydrolysis
- BibHography
I. Metabolism of Sialic Acids
I. Introduction
II. De novo Biosynthesis of Sialic Acids
1. Introduction
2. From Glucose to UDP-N-Acetylhexosamine
3. Formation of NeuSAc
4. Activation and Modification of Neu5Ac
III. Sialyltransfer
1. Introduction
2. Sialyltransfer in Cells and Cell-Free Systems: Cellular Location
a) Intact Cells
- N-Glycosidically Linked Oligosaccharide Chains
- O-Glycosidically Linked Oligosaccharides (Ser/Thr-GalNAc Type)
- Glycolipids (Gangliosides)
- Membrane Glycoconjugates
b) Cell-Free Systems
- N-Glycosidically Linked Oligosaccharide Chains
- O-Glycosidically Linked Oligosaccharide Chains
- Gang Hosides
- Membrane Glycoconjugates
3. Sialyltransferases with N-Glycosidically Linked Oligosaccharide Substrates
4. Sialyltransferases with 0-Glycosidically Linked Oligosaccharide Substrates
5. Sialyltransferases with Glycolipid Substrates
6. Sialyltransferases with Oligosaccharide Substrates
7. Sialyltransferases with Membrane Glycoprotein Substrates
8. Sialyltransferases in Bacterial Systems
9. Ectosialyltransferases
10. Soluble Serum Sialyltransferases
IV. Catabolism of Sialic Acids
1. Introduction
2. CMP-Sialic Acid Hydrolase
3. Sialidases
a) Anomeric Specificity
b) The Carboxyl Group
c) N-Substitution
d) O-Substitution
e) Length of the Side Chain
f) Side Chain or Branch Sialic Acids
g) Influence of Aglycone and Natural Glycosidic Binding Partners
h) Glycosidic Linkage
i) Molecular Parameters
j) Kinetic Parameters and pH Optima
k) Activators and Inhibitors
4. Acylneuraminate Pyruvate-Lyase
a) Bacteria
b) Mammals
V. Uptake and Recycling of Sialic Acids in Cells
VI. Regulation of Sialic Acid Metabolism
1. Introduction
2. Genetic Regulation
3. Regulation of Enzyme Activities
a) Specificity
b) Kinetic Effects
- Substrate and Enzyme Concentration
- Inhibition and Activation
c) Feedback Inhibition
d) Sialuria, a Defect in SiaUc Acid MetaboUsm
4. Nutritional Factors and Energy
5. Spatial Organization
6. Hormonal and Nervous Regulation
- Biblography
J. Biological Significance of Sialic Adds
I. Introduction
II. Role in Cellular Adhesiveness
1. Adhesiveness of Benign Cells
2. Adhesiveness of Transformed and Malignant Cells
III. Influence on the Life-Span of Blood Components
1. Erythrocytes
2. Thrombocytes
3. Lymphocytes
4. Serum Glycoconjugates
IV. Blood Clotting
V. Immunology and Infection
VI. Immunotherapy with Neuraminidase-Treated Cells
VII. Gang Hosides
VIII. Mucins of the Gastrointestinal Tract
IX. Hormones
X. Concluding Remarks and Outlook
- Biblography
K. Sialidoses
I. Introduction
II. Clinical Manifestations and Classification
III. The Metabolic Defect
1. Storage Material
2. The Neuraminidase Defect
3. Pathogenesis
IV. Other Disorders with Neuraminidase Deficiency
V. Laboratory Diagnosis
VI. Summary
- Biblography
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Bibliographische Angaben
- 2012, Softcover reprint of the original 1st ed. 1982, XX, 346 Seiten, 66 Abbildungen, Maße: 17 x 24,4 cm, Kartoniert (TB), Englisch
- Herausgegeben: Roland Schauer
- Verlag: Springer
- ISBN-10: 370918682X
- ISBN-13: 9783709186824
- Erscheinungsdatum: 04.01.2012
Sprache:
Englisch
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