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. Glycolipi…