Sphingolipid Biochemistry

ISBN-13: 9781475703986 / Angielski / Miękka / 2012 / 485 str.

Julian N. Kanfer; Sen-Itiroh Hakomori

Opis

Interest in and emphasis upon different aspects of the sphingolipids have, in general, followed the biochemical developments of the day. The early inves- tigators were preoccupied principally with the isolation of "pure" compounds and structural elucidation. This historical perspective is found in the discus- sion presented in Chapter 1 (Section 1. 1. 2 and Table III). Still, the isolation and structural characterization of glycolipids are the basic foundation of all our knowledge of enzymology, immunology, and cell biology. Recent infor- mation obtained on structure has greatly affected the interpretation of various phenomena related to glycolipids. New structures suggest a new role of gly- colipids as antigens and receptors. Ten years ago, only four neutral glycolipids and two gangliosides were known in human erythrocytes. We now know structures of at least twenty additional neutral glycolipids and ten additional gangliosides in human erythrocytes that are known to be important blood group, heterophil, and autoantigens. Erythrocytes are only one example of a cell type whose glycolipid profile has been extensively studied. Our defective knowledge in immunology and cell biology may be due to incomplete un- derstanding of structural chemistry. Modern methodology based on methyla- tion analysis, mass spectrometry, and enzymatic degradation has supple- mented classical analysis based on clorimetry. Nuclear magnetic resonance spectroscopy is still in the development stage, but will eventually replace var- ious chemical analyses. However, important future studies should be directed toward elucidating the organizational structure of glycolipids in membranes.

Spis treści

1 Chemistry of Glycosphingolipids.- 1.1. Introduction.- 1.1.1. Classification and Nomenclature of Glycosphingolipids.- 1.1.2. Brief History of the Chemistry of Glycosphingolipids.- 1.2. Isolation of Glycosphingolipids.- 1.2.1. Extraction.- 1.2.2. Purification of Lipid Extract: Elimination of Nonlipid Contaminants.- 1.2.3. Separation of Gangliosides and Long-Chain Neutral Glycolipids.- 1.2.4. Separation of Individual Glycolipids.- 1.3. Characterization of Glycosphingolipids.- 1.3.1. Analysis by Thin-Layer Chromatography.- 1.3.2. Characterization of Ceramide Structure, Fatty Acids, and Long-Chain Bases.- 1.3.3. Determination of Carbohydrate Composition.- 1.3.4. Release of Oligosaccharides from Glycosphingolipids.- 1.3.5. Determination of Carbohydrate Sequence.- 1.3.6. Determination of the Position of Glycosyl Linkages.- 1.3.7. Determination of Anomeric Configuration (a or ß) in Glycolipids by Chromium Trioxide Oxidation.- 1.3.8. Direct-Probe Mass Spectrometry of Glycolipids.- 1.3.9. Spectrometric Analysis of Glycosphingolipids: Infrared (IR), Nuclear Magnetic Resonance, and Electron Spin Resonance Spectra.- 1.4. Structure of Glycosphingolipids.- 1.4.1. Structural Variation in Ceramides.- 1.4.2. Simpler Glycosphingolipids: Ceramide Monohexosides, Ceramide Dihexosides, and Sulfatides.- 1.4.3. Globo-Series Glycolipids.- 1.4.4. Lacto-Series Glycolipids.- 1.4.5. Muco-Series Glycolipids: Glycolipids with Digalactosyl to Hexagalactosyl Core Structure.- 1.4.6. Simpler Gangliosides and Hematosides: Sialosyl Glycolipids without Hexosamines.- 1.4.7. Ganglio-Series Glycolipids: Gangliosides with Ganglio-N- triose, Ganglio-N-tetraose, and Ganglio-N-pentaose Structure.- 1.4.8. Glycosphingolipids of Water-Living Invertebrates.- 1.4.9. Plant Sphingolipids (Phytoglycosphingolipids).- 1.5. Chemical Synthesis and Modification of Sphingosines and Glycosphingolipids.- 1.5.1. Synthesis of Long-Chain Bases.- 1.5.2. Synthesis of Glycosphingolipids.- 1.6. Pioneers in Glycolipid Chemistry.- 1.7. References.- 2 Sphingolipid Metabolism.- 2.1. Sphingosine Bases.- 2.1.1. In Vivo Studies.- 2.1.2. In Vivo Studies.- 2.1.3. In Vivo Studies on Sphingosine Base Utilization.- 2.2. The Psychosines.- 2.2.1. Galactosylsphingosine Formation.- 2.2.2. Glucosylsphingosine Formation.- 2.2.3. Galactosylsphingosine Acylation.- 2.2.4. Glucosylsphingosine Acylation.- 2.3. Ceramide (N-Acylsphingosine).- 2.4. Galactosylceramide.- 2.4.1. In Vivo Studies.- 2.4.2. Biosynthesis in Vivo.- 2.4.3. Hydrolysis in Vivo.- 2.5. Ceramide-galactoside-3-sulfate (Sulfatide).- 2.5.1. In Vivo Studies.- 2.5.2. Biosynthesis in Vivo.- 2.5.3. Hydrolysis in Vivo.- 2.6. Glucosylceramide.- 2.6.1. Biosynthesis in Vivo.- 2.6.2. Hydrolysis in Vivo.- 2.7. Ganglioside Metabolism.- 2.7.1. In Vivo Studies.- 2.7.2. Biosynthesis m VeVrö.- 2.8. Sphingomyelin.- 2.8.1. Biosynthesis in Vivo.- 2.8.2. Hydrolysis in Vivo.- 2.9. Biosynthesis of the Sphingolipids: Summary.- 2.10. Hydrolysis of the SpWgolipids: Summary.- 2.11. References.- 3 The Sphingolipidoses.- 3.1. Farber’s Lipogranulomatosis.- 3.1.1. Chemical Studies.- 3.1.2. Enzyme Defect.- 3.2. Krabbe’s Disease (Globoid Cell Leukodystrophy).- 3.2.1. Clinical.- 3.2.2. Pathology.- 3.2.3. Biochemistry.- 3.3. Metachromatic Leukodystrophy.- 3.3.1. Clinical.- 3.3.2. Pathology.- 3.3.3. Biochemistry.- 3.4. Gaucher’s Disease.- 3.4.1. Clinical.- 3.4.2. Pathology.- 3.4.3. Biochemistry.- 3.5. Fabry’s Disease (Angiokeratoma Corporis Diffusium).- 3.5.1. Clinical.- 3.5.2. Pathology.- 3.5.3. Biochemistry.- 3.6. The Gangliosidoses.- 3.6.1. GM2 Gangliosidosis Type I (Classical Tay-Sachs’ Disease).- 3.6.2. GM2 Gangliosidosis Type II (Sandhoff-Jatzkewitz Variant).- 3.6.3. GM2 Gangliosidosis Type III (Juvenile).- 3.6.4. GM1 Gangliosidosis Type I (Pseudo-Hurler’s, Landing’s Syndrome; Neurovisual Lipidosis).- 3.6.5. GM1 Gangliosidosis Type II (Juvenile GMi Gangliosidosis; Derry’s Syndrome).- 3.7. Niemann-Pick’s Disease.- 3.7.1. Clinical.- 3.7.2. Pathology.- 3.7.3. Biochemistry.- 3.8. GM3 Gangliosidosis.- 3.8.1. Pathology.- 3.8.2. Biochemistry.- 3.9. General Comments.- 3.10. References.- 4 Glycosphingolipids in Cellular Interaction, Differentiation, and Oncogenesis.- 4.1. Introduction.- 4.2. Organization and Dynamic State of Glycohpids in Membranes.- 4.2.1. Crypticity and Organization of Glycolipids.- 4.2.2. Association of Membrane Proteins and Glycolipids.- 4.2.3. Dynamic Behavior of Glycolipids in Membranes.- 4.2.4. Common Carbohydrate Chain in Glycolipids and Glycoproteins.- 4.3. Glycolipids in Cellular Interaction and Differentiation.- 4.3.1. Cellular Interaction.- 4.3.2. Glycolipids as Differentiation Markers.- 4.4. Role of Glycolipids in Cell Growth Control.- 4.4.1. Cell Contact Response of Glycolipids as Related to “Contact Inhibition”.- 4.4.2. Cell Cycle and Mitogenesis.- 4.4.3. Glycolipid Addition in Cell Culture.- 4.4.4. Modification by Antiglycolipid Antibodies.- 4.4.5. Glycolipid Changes Caused by Differentiation Inducers.- 4.5. Glycolipid Changes in Oncogenic Transformation: Deficiency in Glycolipid Function.- 4.5.1. Common Features of Glycolipid Changes.- 4.5.2. Studies with Temperature-Sensitive Mutants.- 4.5.3. Comparison of Tumor Cells with Different Degrees of Tumorigenicity, Malignancy, and Metastatic Capability.- 4.5.4. Chemical Carcinogenesis and Glycolipids.- 4.5.5. Studies of Human Cancer.- 4.5.6. Search for Glycolipid Tumor Antigens or Cell-Surface Markers.- 4.5.7. Biological Significance of Tumor-Associated Glycolipid Changes.- 4.6. Glycolipids as Possible Mediators of Immune Response.- 4.6.1 Modulation of B-Cell or T-Cell Response by Gangliosides.- 4.6.2. Gangliosides as Mediators of Immune Cell Recognition.- 4.6.3. Glycolipids as Lymphokine Receptors.- 4.7. Postscript: Enigmas Concerning Glycohpid Functions.- 4.8. References.- 5 Glycolipid Antigens and Genetic Markers.- 5.1. Introduction.- 5.2. General Properties of Glycolipid Antigens.- 5.2.1. Unique Immunogenicity and Antigenicity of Glycolipids.- 5.2.2. Immune Response to Glycolipid Antigens.- 5.2.3. Methods for Detecting Antiglycolipid Antibodies.- 5.3. Heterophil Antigens.- 5.3.1. Forssman Antigen.- 5.3.2. Hanganutziu-Deicher Antigen.- 5.4. Glycolipids with Blood Group AB H Specificities.- 5.5. Glycolipids with Blood Group Lewis (Lea, Leb, Lec and Led) Specificities.- 5.5.1. Lea and Leb Antigens.- 5.5.2. Lec and Led Antigens.- 5.5.3. Lex Antigens and X-Hapten Glycolipids.- 5.6. Glycolipids with Blood Group P, P1, and Pk Specificities.- 5.7. Glycolipids with Blood Group I and i Specificities.- 5.7.1. I and i Antigens and Antibodies.- 5.7.2. Chemical Basis of I and i Specificities.- 5.8. Glycolipids with Blood Group J-Antigen Specificity.- 5.9. Tissue-Specific and Tumor-Associated Glycolipid Antigens.- 5.9.1 Classical Studies.- 5.9.2. Current Studies with Experimental Cancer and Human Cancer.- 5.9.3. Lacto-N-neotetraosylceramide in NILpy Tumor.- 5.9.4. Ganglio-AT-triaosylceramide in Mice Sarcoma and Lymphoma.- 5.9.5. Forssman Antigen in Human Cancer.- 5.9.6. Glycolipid Antigen Specific for SV40-Transformed Hamster Tumors.- 5.9.7. Human Melanoma Antigen Defined by Monoclonal Antibody.- 5.9.8. Burkitt Lymphoma-Associated Antigen Defined by Monoclonal Antibody.- 5.9.9. Monosialo Ganglioside of Human Colon Carcinoma Defined by a Specific Monoclonal Antibody.- 5.9.10. Polyfucosylated Lactosaminolipids in Human Gastrointestinal, Lung, and Liver Adenocarcinoma.- 5.10. Modification of Blood Group Antigens.- 5.10.1. Deletion of A and B Determinants.- 5.10.2. Lewis Fucolipids in Tumors.- 5.10.3. Precursor Accumulation.- 5.10.4. Blood Group Determinants in Human Tumors Foreign to the Host (Illegitimate Blood Group Antigens).- 5.11. Tissue-Specific or Organ-Specific Glycolipid Antigens.- 5.11.1. Tissue-Specific or Organ-Specific Glycolipids.- 5.11.2. Lymphoid-Cell-Type-Specific Glycolipids.- 5.12. Glycolipid Antigens Associated with Autoimmune Processes.- 5.13. References.- 6 Glycosphingolipids as Receptors.- 6.1. Gangliosides and the Serotonin Receptor.- 6.2. Gangliosides and Acetylcholine.- 6.3. Gangliosides and Interferon.- 6.4. Gangliosides and Bacterial Toxins.- 6.4.1. Botulinum Toxin.- 6.4.2. Tetanus Toxin.- 6.4.3. Cholera Toxin.- 6.4.4. Other Toxins.- 6.5. Gangliosides and Lymphocyte Markers.- 6.5.1. Miscellaneous.- 6.6. Gangliosides and Glycoprotein Hormone Receptors.- 6.6.1. Others.- 6.7. Conclusions.- 6.8. References.