Abstract
Glycosphingolipids are the glycosides of N-fatty acylsphingosine, whose trivial name is ceramide. The variety of fatty acids, sphingosines, and carbohydrates results in a great number of glycosphingolipids. Sphingosines are a group of related long-chain aliphatic 2-amino-1,3-diols of which d-erythro- 1,3-dihydroxy-2-amino-4,5-trans-octadecene (sphingosine or sphing-4-enine) occurs most frequently in animal glycosphingohpids. The 4-hydroxylated, saturated compound (phytosphingosine or 4-hydroxysphinganine) and numerous other homologs are found, differing in saturation, branching, and length of the aliphatic chain. Classification of glycosphingolipids has been based on their carbohydrate rather than ceramide moieties, since the structure of the saccharide is dominant in determining their chemical and physical properties. The carbohydrate residue of glycosphingolipids is also a definitive determinant in immunological specificity and may be involved in intercellular recognition. However, the simplest glycolipid, cerebroside, has been subclassified as cerebron, kerasin, nervon, or oxynervon according to the kind of fatty acid present in the ceramide, because the solubility of cerebroside is determined by the kind of fatty acid present. With increasing complexity of carbohydrate structure, however, solubility and other properties are more dependent on the number of carbohydrate residues and their linkages.
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References
Björndal, H., Lindberg, B., and Svensson, S., 1967, Mass spectrometry of partially methylated alditol acetates, Carbohyd. Res. 5:433.
Björndal, H., Hellerqvist, C. G., Lindberg, B., and Svensson, S., 1970, Gas-liquid chromatography and mass spectrometry in methylation analysis of polysaccharides, Angew. Chem. Internat. Ed. 9:610.
Blix, G., 1933, Zur Kenntnis der schwefelhaltigen Lipoidstoffe des Gehirns: Über Cerebronschwefelsäure, Z. Physiol. Chem. 219:82.
Brady, R. O., Fishman, P. H., and Mora, P. T., 1973, Membrane components and enzymes in virally transformed cells. Fed. Proc. 32:102.
Brunius, F. E., 1936, Chemical Studies on the True Forssman Hapten, Aktiebolaget Fahlencrantz Bocktryckerei, Stockholm.
Carter, H. E., and Gaver, R. C., 1967, Improved reagent for trimethylsilylation of sphingo-lipid bases, J. Lipid Res. 8:391.
Carter, H. E., Greenwood, F., and Humiston, C., 1950, Structure of cerebrosides. Fed. Proc. 9:159.
Chambers, R. E., and Clamp, J. R., 1971, An assessment of methanolysis and other factors used in the analysis of carbohydrate-containing materials, Biochem. J. 126:1009.
Eto, T., Ichikawa, Y., Nishimura, K., Ando, S., and Yamakawa, T., 1968, Chemistry of lipid of the posthemolytic residue or stroma of erythrocytes. XVI. Occurrence of ceramide pentasaccharide in the membrane of erythrocytes and reticulocytes of rabbit, J. Biochem. 64:205.
Folch, J., Lees, M., and Sloane-Stanley, G. H., 1957, A simple method for the isolation and purification of total lipids from animal tissues, J. Biol. Chem. 226:497.
Gatt, S., and Rapport, M. M., 1966, Isolation of β-galactosidase and β-glucosidase from brain, Biochim. Biophys. Acta 113:567.
Gaver, R. C., and Sweeley, C. C., 1965, Methods for methanolysis of sphingolipids and direct determination of long-chain bases by gas chromatography, J. Am. Oil Chem. Soc. 42:294.
Gray, G. M., 1971, The effect of testosterone on the biosynthesis of the neutral glycosphingolipids in the C51/BL mouse kidney, Biochim. Biophys. Acta 239:494.
Hakomori, S., 1964, A rapid permethylation of glycolipid and polysaccharide, catalyzed by methylsulfinyl carbanion in dimethyl sulfoxide, J. Biochem. 55:205.
Hakomori, S., 1966, Release of carbohydrates from sphingoglycolipid by osmium-catalyzed periodate oxidation followed by treatment with mild alkali, J. Lipid Res. 7:789.
Hakomori, S., 1970, Glycosphingolipids having blood group ABH and Lewis specificities, Chem. Phys. Lipids 5:96.
Hakomori, S., 1971, Glycolipid changes associated with malignant transformation, in: The Dynamic Structure of Cell Membranes, 22 Colloquium der Gesellschaft Physiologische Chemie (D. Holzl Wallach and H. Fischer, eds.), p. 65, Springer-Verlag, Berlin, New York.
Hakomori, S., 1973, Glycolipids of tumor cell membranes, in: Advances in Cancer Research (S. Weinhouse, ed.). Academic Press, New York, Vol. 18, p. 265.
Hakomori, S., and Andrews, H., 1970, Sphingolipids with Leb activity and the co-presence of Lea and Leb glycolipids in human tumor tissue, Biochim. Biophys. Acta 202:225.
Hakomori, S., and Jeanloz, R. W., 1964, Isolation of a glycolipid having a novel type of ceramide and lacto-N-fucopentaose III, J. Biol. Chem. 239:3656.
Hakomori, S., and Saito, T., 1969, Isolation and characterization of a glycosphingolipid having a new sialic acid. Biochemistry 8:5082.
Hakomori, S., Koscielak, J., Bloch, K. J., and Jeanloz, R. W., 1967, Immunologic relationship between blood group substances and a fucose-containing glycolipid of human adenocarcinoma, J. Immunol. 98:31.
Hakomori, S., Siddiqui, B., Li, Y.-T., Li, S.-C., and Hellerqvist, C. G., 1971, Anomeric structures of globoside and ceramide trihexoside of human erythrocytes and hamster fibroblasts, J. Biol. Chem. 246:2271.
Hakomori, S., Stellner, K., and Watanabe, K., 1972, Four antigenic variants of blood group A glycolipid: Examples of highly complex, branched chain glycolipid of animal cell membrane, Biochem. Biophys. Res. Commun. 49:1061.
Handa, N., and Handa, S., 1965, The chemistry of lipids of posthemolytic residue or stroma of erythrocytes. XIV. Chemical structure of glycolipid of cat erythrocyte stroma, Jap. J. Exptl. Med. 35:332.
Handa, S., and Yamakawa, T., 1964, The chemistry of lipids of posthemolytic residue or stroma of erythrocytes. XII. Chemical structure and chromatographic behavior of hematosides obtained from equine and dog erythrocytes, Jap. J. Exptl. Med. 34:293.
Handa, S., Ariga, T., Miyatake, T., and Yamakawa, T., 1971, Presence of α-anomeric glycosidic configuration in the glycolipids accumulated in kidney with Fabry’s pancreas, J. Biochem. 69:625.
Iijima, Y., Muramatsu, T., and Egami, F., 1971, Purification of α-l-fucosidase from the liver of a marine gastropod, Turbo cornutus, and its action on blood group substances, Arch. Biochem. Biophys. 145:150.
Ishizuka, I., Kloppenburg, M., and Wiegandt, H., 1970, Characterization of gangliosides from fish brain, Biochim. Biophys. Acta 210:299.
Johnson, G. A., and McCluer, R. H., 1963, Isolation and analysis of mono-, di-, and trisialogangliosides, Biochim. Biophys. Acta 70:487.
Karlsson, K. A., Samuelson, B. E., and Stern, G. O., 1971, Lipid pattern and Na+-K+- dependent adenosine triphosphatase activity in the salt gland of duck before and after adaptation to hypertonic salines, J. Membrane Biol. 5:169.
Kawanami, J., and Tsuji, T., 1971, Structure of the oligosaccharides from mammalian glycolipids, Chem. Phys. Lipids 7:49.
Klenk, E., 1939, Beiträge zur Chemie des Lipoidosen: Niemann-Picksche Krankheit und amaurotische Idiotie, Z. Physiol. Chem. 262:128.
Klenk, E., 1940, Beiträge zur Chemie des Lipoidosen, Z. Physiol. Chem. 267:128.
Klenk, E., 1942, Über die Ganglioside eine neue Gruppe von zuckerhaltigen Gehirnlipoiden, Z. Physiol. Chem. 273:76.
Klenk, E., and Choppin, P. W., 1970, Glycosphingolipids of plasma membranes of cultured cells and an enveloped virus (SVS) grown in these cells, Proc. Natl. Acad. Sci. 66:57.
Klenk, E., and Heuer, K., 1960, Gangliosides of dog erythrocytes. Deutsch. Z. Verdau. Stoffwechsel. 20:180.
Klenk, E., and Lauenstein, K., 1952, Zur Kenntnis der Kohlenhydratengruppen des Submaxillarismucins und Hammucoproteids: Die Isolierung von Neuraminsäure als Spaltprodukt, Z. Physiol. Chem. 291:147.
Klenk, E., and Padberg, G., 1962, Über die Ganglioside von Pferderythrocyten, Z. Physiol. Chem. 327:249.
Klenk, E., and Rennkampf, F., 1942, Der Zucker im Cerebrosid der Milch bei Gaucher Krankheit, Z. Physiol. Chem. 272:280.
Kuhn, R., and Wiegandt, H., 1963, Die Konstitutionen der Ganglio-N-tetraose und des Gangliosids GI, Chem. Bericht. 96:866.
Laine, R. A., Esselman, W. J., and Sweeley, C. C., 1972a, Gas-liquid chromatography of carbohydrates, in: Methods of Enzymology, Vol. XXVIII (V. Ginsburg, ed.), pp. 159–167, Academic Press, New York.
Laine, R. A., Sweeley, C. C., Li, Y.-T., Kisic, A., and Rapport, M. M., 1912b, On the structure of cytolipin R, a ceramide tetrahexoside from rat lymphosarcoma, J. Lipid Res. 18:519.
Ledeen, R., and Salsman, K., 1965, Structure of the Tay-Sachs ganglioside. Biochemistry 4:2225.
Lemieux, R. U., Kullnig, R. K., Bernstein, H. J., and Schneider, W. G., 1958, Configurational effects on the proton magnetic resonance spectra of six-membered ring compounds, J. Am. Chem. Soc. 80:6098.
Li, S.-C., and Li, Y.-T., 1970, Studies on the glycosidases of jack bean meal. III. Crystallization and properties of β-N-acetylhexosaminidase, J. Biol. Chem. 245:5153.
Li, S.-C., and Li, Y.-T., 1971, Anomeric configuration of galactose residues in ceramide trihexosides, J. Biol. Chem. 246:3769.
Li, Y.-T., and Li, S.-C., 1968, Isolation of glycopeptides from rat liver microsomes involved in the biosynthesis of plasma glycoprotein, J. Biol. Chem. 243:3994.
Li, Y.-T., Li, S.-C., and Dawson, G., 1972, Anomeric structure of ceramide digalactoside isolated from the kidney of a patient with Fabry’s disease, Biochim. Biophys. Acta 260:88.
Makita, A., and Yamakawa, T., 1962, Biochemistry of organ glycolipids. I. Ceramide oligohexosides of human, equine, and bovine spleens, J. Biochem. 51:121.
Makita, A., and Yamakawa, T., 1963, The glycolipids of the brain of Tay-Sachs disease: The chemical structures of a globoside and main ganglioside, Jap. J. Exptl. Med. 33:361.
Makita, A., Iwanaga, M., and Yamakawa, T., 1964, The chemical structure of human kidney globoside, J. Biochem. 55:202.
Makita, A., Suzuki, C., and Yosizawa, Z., 1966, Chemical and immunological characterization of Forssman hapten isolated from equine organs, J. Biochem. 60:502.
Martensson, E., 1966, Sulfatides of human kidney: Isolation, identification, and fatty acid composition, Biochim. Biophys. Acta 116:521.
McIUwain, H., 1963, Chemical Exploration of the Brain, Elsevier, Amsterdam.
Penick, R. J., Meisler, M. H., and McCluer, R. H., 1966, Thin layer chromatographic studies of human brain gangliosides Biochim. Biophys. Acta 116:279.
Puro, K., 1969, Carbohydrate components of bovine-kidney gangliosides, Biochim. Biophys. Acta 189:401.
Rapport, M. M., and Graf, L., 1969, Immunochemical reactions of lipids, Progr. Allergy 13:273.
Rapport, M. M., Graf, L., Skipski, V. P., and Alonzo, N. F., 1959, Immunochemical studies of organ and tumor lipids. VI. Isolation and properties of cytolipin H, Cancer 12:438.
Rapport, M. M., Graf, L., and Alonzo, N. F., 1960, Immunochemical studies of organ and tumor lipids. VIII. Comparison of human tumor and ox spleen cytosides, J. Lipid Res. 1:301.
Rapport, M. M., Schneider, H., and Graf, L., 1967, Cytolipin R: A pure lipid hapten isolated from rat lymphosarcoma, Biochim. Biophys. Acta 137:409.
Roseman, S., 1970, The synthesis of complex carbohydrates by multi-glycosyltransferase systems and their potential function in intercellular adhesion, Chem. Phys. Lipids 5:270.
Rouser, G., Kritchevsky, D., Heller, D., and Lieber, E., 1963, Lipid composition of beef brain, beef liver, and the sea anemone: Two approaches to quantitative fractionation of complex lipid mixtures, J. Am. Oil Chem. Soc. 40:425.
Saito, T., and Hakomori, S., 1971, Quantitative isolation of total glycosphingolipids from animal cells, J. Lipid Res. 12:257.
Siddiqui, B., and Hakomori, S., 1970, Change of glycolipid pattern in Morris hepatoma 5123 and 7800, Cancer Res. 30:2930.
Siddiqui, B., and Hakomori, S., 1971, A revised structure for the Forssman glycolipid hapten, J. Biol. Chem. 246:5766.
Siddiqui, B., and Hakomori, S., 1973, A ceramide tetrasaccharide of human erythrocyte membrane reacting with anti-type XIV pneumococcal polysaccharide antiserum, Biochim. Biophys. Acta 330:147.
Siddiqui, B., and McCluer, R. H., 1968, Lipid components of sialosylgalactosylceramide of human brain, J. Lipid Res. 9:366.
Siddiqui, B., Kawanami, J., Li, Y.-T., and Hakomori, S., 1972, Structures of ceramide tetrasaccharide from various sources: Uniqueness of rat kidney ceramide tetrasaccharide, J. Lipid Res. 13:657.
Smith, L., and Unrau, A. M., 1959, On the presence of 1 → 6 linkages in laminarin, Chem. Ind. 1959:881.
Stellner, K., Watanabe, K., and Hakomori, S., 1973b, Isolation and characterization of glycosphingolipids with blood group H specificity from membrane of human erythrocytes, Biochemistry 12:656.
Stellner, K., Saito, H., and Hakomori, S., 1973b, Determination of aminosugar linkages in glycolipids by methylation: Aminosugar linkage of ceramide pentasaccharide of rabbit erythrocytes and of Forssman antigen. Arch. Biochem. Biophys. 155:464.
Stoffyn, A., Stoffyn, P., and Martensson, E., 1968, Structure of kidney ceramide dihexoside sulfate, Biochim. Biophys. Acta 152:353.
Stoffyn, P., and Stoffyn, A., 1963, Structure of sulfatides, Biochim. Biophys. Acta 70:218.
Svennerholm, L., Chromatographic separation of human brain gangliosides, J. Neurochem. 10:613.
Sweeley, C. C., and Klionsky, B., 1963, Fabry’s disease: Classification as a sphingolipidosis and partial characterization of a novel glycolipid, J. Biol. Chem. 238:3148.
Sweeley, C. C., and Walker, B., 1964, Determination of carbohydrates in glycolipids and gangliosides by gas chromatography. Anal. Chem. 36:1461.
Szulman, A. E., 1966, Chemistry, distribution, and function of blood group substances, Ann. Rev. Med. 17:307.
Thudicum, J. L. W., 1874, Report of Med. Officer of Privy Council (Local Govn’t Board, new series III, 13, Loman). Cited by Tierfelder, H., and Klenk, E., 1930, in: Chemie der Cerebroside and Phospholipide, Springer-Verlag, Berlin.
Thudicum, J. L. W., 1904, Die chemische Konstitutionen des Gehirns des Menschen und der Tiere, Cranz Pietzscher, Tubingen.
van der Veen, J. M., 1963, An n.m.r. study of the glycoside link in glycosides of glucose and galactose, J. Org. Chem. 28:564.
Vance, D., and Sweeley, C. C., 1967, Quantitative determination of the neutral glycosyl ceramides in human blood, J. Lipid Res. 8:621.
Volk, B. W., and Aronson, S. M., 1972, Sphingolipids, sphingolipidoses and allied disorders, in: Advances in Experimental Medicine and Biology, Vol. 19, Plenum Press, New York, London
Watanabe, K., and Hakomori, S., 1973, A glycosphingolipid sharing reactivity with both wheat germ lectin and “carcinoembryonic antisera(GOLD)”: Partial identity of the reactive sites, FEBS Letters 37:317.
Weissman, B., and Hinrichson, D. F., 1969, Mammalian α-acetylgalactosaminidase: Occurrence, partial purification, and action on linkages in submaxillary mucin. Biochemistry 8:2034.
Wherrett, J., and Hakomori, S., 1973, Characterization of a blood group B glycolipid accumulating in the pancreas of a patient with Fabry’s disease, J. Biol. Chem. 248:3046.
Wiegandt, H., 1970, Gangliosides of extraneuronal tissue, Chem. Phys. Lipids 5:198.
Wiegandt, H., 1972, Recent advances on the chemistry and localization of brain gangliosides and related glycosphingolipids, in: Glycolipids, Glycoproteins and Mucopolysaccharides of Nervous System (V. Zambotti, G. Tettamanti, and M. Arrigoni, eds.), p. 127, Plenum Press, New York, London.
Wiegandt, H., and Baschung, G., 1965, Die Gewinnung des Zuckeranteiles der Glykosphingolipide durch Ozonolyse und Fragmentierung, Z. Naturforsch. 20:164.
Wood, R. D., Raju, R. K., and Reiser, R., 1965, Gas-liquid chromatographic analysis of monoglycerides as their trimethylsilyl ether derivatives, J. Am. Oil Chem. Soc. 42:161.
Yamakawa, T., 1966, Glycolipids of mammalian red blood cells, in: 16 Colloquium der Gesellschaft Physiologische Chemie (E. Schüte, ed.), p. 87, Springer-Verlag, Berlin, New York.
Yamakawa, T., and Suzuki, S., 1951, The chemistry of the lipids of posthemolytic residue or stroma of erythrocytes. I. Concerning the ether-insoluble lipids of lyophilized horse blood stroma, J. Biochem. 38:99.
Yamakawa, T., and Suzuki, S., 1952, The chemistry of the lipids of posthemolytic residue or stroma of erythrocytes. II. On the structure of hemataminic acid, J. Biochem. 39:393.
Yamakawa, T., Irie, R., and Iwanaga, M., 1960, The chemistry of lipid of posthemolytic residue or stroma of erythrocytes. IX. Silicic acid chromatography of mammalian stroma glycolipids, J. Biochem. 48:490.
Yamakawa, T., Kiso, N., Handa, S., Makita, A., and Yokoyama, S., 1962, On the structure of brain cerebroside sulfuric ester and ceramide dihexoside of erythrocytes, J. Biochem. 52:226.
Yamakawa, T., Yokoyama, S., and Handa, N., 1963, Chemistry of lipids of posthemolytic residue or stroma of erythrocytes. XI. The structure of globoside, the main mucolipid of human erythrocytes, J. Biochem. 53:28.
Yamakawa, T., Nishimura, S., and Kamimura, M., 1965, The chemistry of lipids of posthemolytic residue or stroma of erythrocytes. XIII. Further studies on human red cell glycolipids, Jap. J. Exptl. Med. 35:201.
Yang, H.-J., and Hakomori, S., 1971, A sphingolipid having a novel type of ceramide and lacto-N-fucopentaose III, J. Biol. Chem. 246:1192.
Yogeeswaran, G., Wherrett, J., Chatterjee, S., and Murray, R. K., 1970, Gangliosides of cultured mouse cells, J. Biol. Chem. 245:6718.
Zambotti, V., Tettamanti, G., and Arrigoni, M., 1972, Glycolipids, Glycoproteins, and Mucopolysaccharides of the Nervous System, Plenum Press, New York, London.
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Laine, R.A., Stellner, K., Hakomori, SI. (1974). Isolation and Characterization of Membrane Glycosphingolipids. In: Korn, E.D. (eds) Methods in Membrane Biology. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-8960-0_3
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