Abstract
The sphingolipids are a class of compounds quite analogous to the lipid series derived from glycerol. Just as glycerol can form a series of phosphorous containing complex lipids, i. e., lecithin, cephalin, etc. (cf. chap, by Rossiter, p. 93), sphingosine can combine with fatty acids, phosphorous, and bases to give rise to the sphingomyelins. The glycerides can form complex lipids with sugars (Putnam and Hassid 1954, Carter et al. 1956) — and, in a similar manner, sphingosine can form a series of complex sugar-containing lipids, i.e., psychosine, cerebrosides, cerebroside sulfate and gangliosides (Deuel 1951, Celmer and Carter 1952). The chemistry of the glycerol and sphingosine containing lipids has been reviewed in other chapters in this volume. The similarity of structure between phosphatidylcholine and sphingomyelin is apparent. Thus the 1 carbon is substituted with phosphoryl choline and carbons 2 and 3 contain long chain fatty acid and/or hydrocarbon residues. In the case of glycerol carbon 3 is substituted with a fatty acid, whereas sphingomyelin contains a hydrocarbon residue joined by carbon-carbon covalent bonding to carbon 3 as an integral part of the sphingosine molecule. If indeed the properties of the glycerol and sphingosine containing lipids are similar, as illustrated by the phosphoryl choline containing derivatives, then one can ask what are the roles of these classes of lipids and why are both classes important to the physiological functioning of animals?
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Agranoff, B. W., N. Radin, and W. Suomi: Enzymic oxidation of cerebrosides: studies on Gaucher’s disease. Biochim. biophys. Acta (Amst.) 57,194 (1962).
Aminoff, D., F. Dodyk, and S. Roseman: Enzymatic synthesis of colominic acid. J. biol. Chem. 238, 1177 (1963).
Aronson, S. M., and B. W. Volk: Cerebral Sphingoiipidosis. New York: Academic Press, Inc. 1962.
Bakke, J. E., and W. E. Cornatzer: Metabolism of brain and liver sulfatides. J. biol. Chem. 236, 653 (1961).
Bandtjrski, R. S., L. G. Wilson, and C. L. Squires: The mechanism of “active sulfate” formation. J. Amer. chem. Soc. 78, 6408 (1956).
Bartsch, G.: Incorporation of Acetate-1-C14 into Sphingolipids of the Rat Brain. VI. Int. Congress Biochem. Abst., p. 564, 1963.
Basu, S., and B. Kaufman: Ganglioside synthesis in embryonic chicken brain. Fed. Proc. 24, 479 (1965).
Blix, G. : Zur Kenntnis der schwefelhaltigen Lipoidstoffe des Gehirns über Cerebronschwefelsäure. Hoppe-Seylers Z. physiol. Chem. 219, 82 (1933).
Bogoch, S. : Aminoglycolipids and glycoproteins of human brain. III. Quantitative separation and determination of brain glycoproteins neuraminic acid, hexosamine, and hexoses by means of whole tissue emulsion-fractionation. Nature (Lond.) 190, 153 (1961).
Brady, R. O. : Studies on the total enzymatic synthesis of cerebrosides. J. biol. Chem. 237, 2416 (1962).
Brady, R. O., J. V. Formica, and G. J. Koval: The enzymatic synthesis of sphingosine. II. Further studies on the mechanism of the reaction. J. biol. Chem. 233, 1072 (1958b).
Brady, R. O., J. N. Kanfer, and D. Shapiro: The metabolism of glucocerebrosides. I. Purification and properties of a glucocerebroside cleaving enzyme from spleen tissue. J. biol. Chem 240, 39 (1964).
Brady, R. O., J. N. Kanfer, and D. Shapiro: Metabolism of glucocerebrosides. II. Evidence of an enzymatic deficiency in Gaucher’s disease. Biochem. biophys. Res. Commun. 18, 221 (1965).
Brady, R. O., G. J. Koval: Biosynthesis of sphingosine in vitro. J. Amer. chem. Soc. 79, 2648 (1957)
Brady, R. O., G. J. Koval: The enzymatic synthesis of sphingosine. J. biol. Chem. 233, 26 (1958a)
Brande, G. in Folch-Pi (editor): Pathology of the nervous system, p. 57, London: Pergamon Press, 1961.
Burton, R. M. : Uridine nucleotides and the metabolism of nerve tissue. R. O. Brady, and D. Tower, editors, Neurochemistry of Nucleotides and Amino Acids, published by John Wiley and Sons, Inc. 1960.
Burton, R. M. : The action of neuraminidase from Clostridium perfringens on gangliosides. J. Neurochem. 10, 503 (1963).
Burton, R. M., Y. M. Balfour, and J. M. Gibbons: Gangliosides and cerebrosides turnover rates in rat brain. Fed. Proc. 23, 230 (1964).
Burton, R. M., L. Garcta-Bunuel, M. Golden, and Y. Balfour: Incorporation of radioactivity of D-glucosamine-1-C14, D-glucose-1-C14, D-galactose-1-C14, and DL-serine-3-C14 into rat brain glycolipids. Biochemistry 2, 580 (1963).
Burton, R. M., M. A. Sodd, and R. O. Brady: The incorporation of galactose into galactolipides. J. biol. Chem. 233,1053 (1958).
Burton, R. M., M. A. Sodd, and R. O. Brady: The involvement of uridine nucleotides in the biosynthesis of galactolipids in the central nervous system, in F. Brücke, editor, Fourth Int. Cong, of Biochem. Vol. Ill Biochemistry of the Central Nervous System 202 (1959).
Burton, R. M., M. A. Sodd, and E. R. Stadtman: The oxidation of acetaldehyde to acetyl coenzyme A. J. biol. Chem. 202, 873 (1953).
Cardini, C. E., and L. F. Leloir: Enzymatic formation of acetylgalactosamine. J. biol. Chem. 225, 317 (1957).
Carter, H. E., F. J. Glick, W. P. Norris, and G. E. Phillips: Biochemistry of the sphingo-lipids. III. Structure of sphingosine. J. biol. Chem. 170, 285 (1947).
Carter, H. E., W. D. Celmer, W. E. M. Lands, K. L. Mueller, and H. H. Tomizawa: Biochemistry of the sphingolipids. VIII. Occurrence of a long chain base in plant phosphatides. J. biol. Chem. 206, 613 (1954).
Carter, H. E., and Y. Fujino: Biochemistry of the sphingolipids. IX. Configuration of cerebrosides. J. biol. Chem. 221, 879 (1956).
Carter, H. E., D. S. Galanos, and Y. Fujino: Chemistry of the sphingolipids. Canad. J. Biochem. 34, 320–331 (1956).
Carter, H. E., R. A. Hendry, S. Nojima, N. Z. Stanacev, and K. Ohno: Biochemistry of the sphingolipids. XIII. Determination of the structure of cerebrosides from wheat flour. J. biol. Chem. 236, 1912 (1961).
Carter, H. E., and C. G. Humiston: Biochemistry of the sphingolipids. V. The structure of sphingosine. J. biol. Chem. 191, 727 (1951).
Carter, H. E., R. H. McCluer, and E. D. Slifer: Lipids of wheat flour. I. Characterization of galactosyl-glycerol components. J. Amer. chem. Soc. 78, 3735 (1956).
Carter, H. E., W. P. Norris, F. J. Glick, G. E. Phillips, and R. Harris: Biochemistry of the sphingolipids II. Isolation of dihydrosphingosine from the cerebroside fractions of beef brain and spinal cord. J. biol. Chem. 170, 269 (1949).
Carter, H. E., D. Shapiro, and J. B. Harrison: Synthesis and configuration of dihydrosphingosine. J. Amer. chem. Soc. 75, 1007 (1953).
Carubelli, R., R. E. Trucco, and R. Caputto : Neuraminidase activity in mammalian organs. Biochem. biophys. Acta (Amst.) 60, 196 (1962).
Celmer, W. D., and H. E. Carter: Chemistry of phosphatides and cerebrosides. Physiol. Rev. 32, 167 (1952).
Chou, T. C. and M. Soodak: The acetylation of D-glucosamine by pigeon liver extracts. J. biol. Chem. 196,105 (1952).
Christianson, O. O.: Experimental lesions produced by cerebrosides. Arch. Path. (Chic.) 32, 369 (1941).
Cleland, W. W., and E. P. Kennedy: The enzymatic synthesis of psychosine. J. biol. Chem. 235. 45 (1960).
Comb, D. G., and S. Roseman: Enzymatic synthesis of N-acetyl-D-mannosamine. Biochim. biophys. Acta (Amst.) 29, 653 (1958).
Crocker, A. C, and S. Farber: Niemann-Pick disease: A review of eighteen patients. Medicine (Baltimore) 37, 1 (1958).
Cumings, J. N., H. Goodwin, E. M. Woodward, and G. Curzon: Lipids in the brains of infants and children. J. Neurochem. 2, 289 (1958).
Davidson, E. A., H. J. Blumenthal, and S. Roseman: Glucosamine metabolism. II. Studies on glucosamine-6-phosphate N-acetylase. J. biol. Chem. 226, 125 (1957).
Davison, A. N., and M. Wajda: Metabolism of myelin lipids: Estimation and separation of brain lipids in the developing rabbit. J. Neurochem. 4, 353 (1959).
Davison, A. N., and N. A. Gregson: The physiological role of cerebron sulphuric acid (sulphatide) in the brain. Biochem. J. 85, 558 (1962).
Deuel, H. J. : The lipids. Vol. I. New York: Chemistry Interscience Press, Inc. 1951.
Fairbairn, D. : The phospholipase of the venom of the cotton-mouth moccasin (Agkistridon piscivorus L). J. biol. Chem. 157, 633 (1945).
Fields, M., and S. Gatt: Absorption of 1-C14 lignoceric acid in the rat. Nature (Lond.) 198, 994 (1963).
Folch-Pi, J. : Chemical Pathology of the Nervous System. London: Pergamon Press, 1961.
Folch-Pi, J. and H. Bauer: Brain Lipids and Lipoproteins, and the Leucodystrophies. Amsterdam: Elsevier 1963.
Folch-Pi, J., A. Meath, and S. Arsove: Isolation of brain strandin, a new type of large molecule tissue component. J. biol. Chem. 191, 819 (1951).
Folch-Pi, J. in M. Waelsch: Biochemistry of the Developing Nervous System, p. 121. New York: Academic Press, Inc. 1955.
Fujino, Y., and T. Negishi: Studies on the conjugated lipids. Part XL Hydrolysis of cere-broside sulfate by shellfish liver enzyme. Bull. Agr. Chem. Soc. Japan, 21, 225 (1957).
Fujino, Y., and I. Zabin: Studies on conjugated lipids. Agricultural and Biological Chemistry 26, 267 (1962a).
Fujino, Y., and I. Zabin: The configuration of sphingosine synthesized in rat brain homogenates. J. biol. Chem. 237, 2069 (1962b).
Gatt, S.: Enzymic hydrolysis and synthesis of ceramides. J. biol. Chem. 238, 3131 (1963a).
Gatt, S.: Metabolism of (1-C14) lignoceric acid in the rat. Biochim. biophys. Acta (Amst.) 70, 370 (1963b).
Gatt, S., and E. R. Berman: Studies on brain lipids in Tay-Sach’s disease. I. Isolation of two sialic acid-free glycolipids. J. Neurochem. 10, 43 (1963).
Gatt, S., and E. R. Berman and B. Shapiro: Metabolism of 1-C14 C lignoceric acid in the rat. Nature (Lond.) 185,461 (1960).
Ghosh, S., and S. Roseman: Enzyme phosphorylation of N-acetyl-D-mannosamine. Proc. nat. Acad. Sci. (Wash.) 47, 955 (1961).
Ghosh, S., and S. Roseman: Enzymatic interconversion of N-acetylglucosamine and N-acetylmannosamine. Fed. Proc. 21, 89 (1962).
Glaser L.: Biosynthesis of deoxysugars. Physiol. Rev. 43, 215 (1963)
Goldberg, I. H.: Enzymatic sulfuryiation mechanisms. Dissertation, Rockefeller Institute, New York 1960a.
Glaser, L.: Parallels between enzymatic sulfuryiation of N-acetyl sphingosine and chloramphemicol. Fed. Proc. 19, 220 (1960b).
Glaser, L.: The sulfolipids. J. Lipid Res. 2, 103 (1961).
Glaser, L., and A. Delbrück: Transfer of sulfate from 3’-phosphoadenosine-5’-phosphosulfate to lipids, mucopolysaccharides and aminoalkyl phenols. Fed. Proc. 18, 235 (1959).
Gould, R. G., F. M. Sinex, I. N. Rosenberg, A. K. Solomon, and A. B. Hastings: Excretion of radioactive carbon dioxide by rats after administration of isotopie bicarbonate, acetate, and succinate. J. biol. Chem. 177, 295 (1949).
Graf L., and M. M. Rapport: Immunochemical studies of organ and tumor lipids. VII. The reactivity of anti-human tumor sera with cytolipin H. cardiolipin, and forssman haptens. Cancer Res. 20, 546 (1960).
Green, J. P., and J. D. Robinson jr.: Cerebroside sulfate (sulfatide A) in some organs of the rat and in a mast cell tumor. J. biol. Chem. 235, 1621 (1960)
Hagberg, B., P. Sourander, L. Svennerholm, and H. Voss: Late infantile metachromatic leucodystrophy of the genetic type. Acta paediat. (Uppsala) 49, 135 (1960).
Hagberg, B., P. Sourander, L. Svennerholm, and H. Voss: Clinical and laboratory diagnosis of metachromatic leucodystrophy. Cerebr. Palsy Bull. 3, 438 (1961).
Hagberg, B., P. Sourander, L. Svennerholm, and H. Voss: Sulfatide lipidoses in childhood. Amer. J. Dis. Childr. 104, 644 (1962).
Hagberg, B., P. Sourander, L. Svennerholm, and H. Voss: Diagnosis of Krabbe’s infantile leucodystrophy. J. Neurol. Neurosurg. Psychiat. 26, 195 (1963).
Hajra, A. K., and N. S. Radin: Biosynthesis of the cerebroside odd-numbered fatty acids. J. Lipid Res. 3, 327 (1962).
Hajra, A. K., and N. S. Rad: Biosynthesis of odd- and even-numbered cerebroside fatty acids: Evidence for two routes. Biochim. biophys. Acta (Amst.) 70, 97 (1963a).
Hajra, A. K., and N. S. Rad: Isotopie studies of the biosynthesis of the cerebroside fatty acids in rats. J. Lipid Res. 4, 270 (1963b).
Hajra, A. K., and N. S. Rad: In vivo conversion of labeled fatty acids to the sphingolipid fatty acids in rat brain. J. Lipid Res. 4, 448 (1963c).
Hajra, A. K., and N. S.: Cerebroside galactosidase of pig brain. Fed. Proc. 24, 360 (1965).
Hauser, G. : Labeling of cerebrosides and sulfatides in rat brain. Biochim. biophys. Acta (Amst.) 84, 212 (1964).
Heald, P. J., and M. A. Robinson: The metabolism of sulphatides in cerebral tissues. Bio J. chem. J. 81,157(1961).
Heller, M., and B. Shapiro: The hydrolysis of sphingomyelin by rat liver. Israel J. Chem. 1, No. 3a (1963).
Holtz, A. I., B. W. Uhlendorf, and D. S. Fredrickson: Persistence of a lipid defect in tissue cultures derived from patients with Niemann-Pick disease. Fed. Proc. 23,128 (1964).
Hutchens, T. T., J. T. van Bruggen, and E. S. West: Fatty acid and cholesterol synthesis rates in the intact rat. Arch. Biochem. 52, 261 (1954).
Ivemark, B. I., L. Svennerholm, C. Throen, and R. Tunell: Niemann-Pick disease in infancy. Acta paediat. (Uppsala) 52, 391 (1963).
Jatzkewitz, H. : Zwei Typen von Cerebrosid-Schwefelsäureestern als sogenannte „Prälipoide” und Speichersubstanzen bei der Leukodystrophie, Typ Scholz (metachromatische Form der diffusen Sklerose). Hoppe-Seylers Z. physiol. Chem. 311, 279 (1958).
Jatzkewitz, H., H. Pilz, u. H. Holländer: Biochemische und vergleichende histochemische Untersuchungen in umschriebenen Gebieten des Gehirns bei Fällen von adulter und infantiler metachromatischer Leukodystrophie. Acta neuropath. (Beri.) 4, 75 (1964).
Jatzkewitz, H., H. Pilz and K. Sandhoff: The quantitative determination of gangliosides and their derivatives in different forms of amaurotic idiocy. J. Neurochem. 12,135 (1965).
Jenny, E. F., and C. A. Grob : Die Synthese von Erythro-dihydrosphingosin aus Trans-2-octadecen-1-Säure. Helv. chim. Acta 36,1936 (1953).
Joffe, S., and M. M. Rapport: Identification of an organ specific lipid hapten in brain. Nature (Lond.) 197, 60 (1963).
Jourdian, G. W., D. M. Carlson, and S. Roseman: The enzymatic synthesis of sialyl-lactose. Biochem. biophys. Res. Commun. 10, 352 (1963).
Kalckar, H. M., and E. S. Maxwell: Biosynthesis and metabolic function of uridine diphos-phoglucose in mammalian organisms and its revelance to certain inborn errors. Physiol. Rev. 38, 77 (1958).
Kanfer, J. N., and R. O. Brady: Studies on the structure of gangliosides. I. On the linkage of N-acetyl neuraminic acid in monosialoganglioside. Biochem. biophys. Res. Commun. 11, 267 (1963).
Kanfer, J. N., R. S. Blacklow, L. Warren, and R. O. Brady: The enzymatic synthesis of gangliosides. Biochem. biophys. Res. Commun. 14, 287 (1964).
Karlsson, K. A.: Studies on sphingosines. 3. C20-dihydrosphingosine, a hitherto unknown sphingosine. Acta chem. scand. 18, 565 (1964).
Karlsson, K. A.: Studies on sphingosines. 4. Composition of sphingomyelins from human plasma. Proc. biochem. Soc. 92, 39 (1964).
Kataoka, T. : Sulfur metabolism of the nervous system. III. Incorporation of S35 into sulfur-containing lipids of the brain following intracisternal injection of sodium sulfate-S35. Nara Igaku Zasshi 13, 7 (1962).
Kishimoto, Y., and N. S. Radin : Structures of the 2-hydroxy unsaturated fatty acids of pig brain sphingolipids. J. Lipid Res. 5, 94 (1964).
Kiss, J., G. Fodor, and D. Banfi: Zurückführung der Konfiguration des (natürlichen) Sphingosins auf die der D-erythro-2-amino-3,4-dioxy-Buttersäure. 12. Mitteilung über Sphingosin und Sphingolipoide. Helv. chim. Acta 37, 1471 (1954).
Klenk, E.: Über Sphingosin (10. Mitteilung über Cerebroside). Hoppe-Seylers Z. physiol. Chem. 185, 169(1929).
Klenk, E.: Beiträge zur Chemie der Lipoidosen. 3. Niemann-Picksche Krankheit und amaurotische Idiotie. Hoppe-Seylers Z. physiol. Chem. 262, 128 (1939).
Klenk, E. u. H. Faillard: Über Sphingosin. Hoppe-Seylers Z. physiol. Chem. 299, 48 (1955).
Klenk, E. u. W. Gielen: Zur Kenntnis der Ganglioside des Gehirns. Hoppe-Seylers Z. physiol. Chem. 319, 283 (1960).
Klenk, E. u. W. Gielen: Über ein chromatographisch einheitliches hexosaminhaltiges Gangliosid aus Menschengehirn. Hoppe-Seylers Z. physiol. Chem. 326,158 (1961).
Klenk, E. u. W. Gielen and G. Padberg, in S. M. Aronson, and B. W. Volk: Cerebral Sphingolipidoses, p. 301 New York: Academic Press, Inc. 1962.
Klenk, E. u. W. Gielen, U. W. Hendricks, u. W. Gielen: ß-D-galaktosido-(l→3)-N-acetyl-D- Galaktosamine in kristallisiertem Disaccharid aus menschlichen Gehirngangliosiden. Hoppe-Seylers Z. physiol. Chem. 330, 140 (1963a).
Klenk, E. u. W. Gielen, U. W. Hendricks: Über ein zweites hexosaminhaltiges Gangliosid aus Menschengehirn. HoppeSeylers Z. physiol. Chem. 330, 218 (1963b).
U. Liedtke, u. W. Gielen: Das Gangliosid des Gehirns bei der infantilen amaurotischen Idiotie vom Typ Tay-Sachs. Hoppe-Seylers Z. physiol. Chem. 334,186 (1963).
U. Liedtke, u. F. Rennkamp:Über die Ganglioside und Cerebroside der Rindermilz. Hoppe-Seylers Z. physiol. Chem. 273, 253 (1942).
U. Liedtke, in H. Waelsch: Biochemistry of the Developing Nervous System, p. 397 New York: Academic Press Inc. 1961.
Kochetkov, N. K., I. G. Zhukova, and I. S. Glukgoded : Sphingoplasmalogens. A new type of sphingolipids. Biochim. biophys. Acta (Amst.) 70, 716 (1963).
Kochetkov, N. K., I. G. Zhukova, and I. S. Glukgoded: Sphingoplasmalogens, a new type of sphingolipid. Biokhima 29, 570 (1964).
Koch, W. : Zur Kenntnis der Schwefelverbindungen des Nervensystems. Hoppe-Seylers Z. physiol. Chem. 53, 496 (1907).
Kopaczyk, K. C and N. S. Radin: Metabolie conversions of cerebroside by brain. Fed. Proc. 23,230(1964).
Kopaczyk, K. C and N. S. Radin In vivo conversions of cerebroside and ceramide in rat brain. J. Lipid Res. 6,140 (1965).
Korey, S. R., and A. Stein: A gangliosidase system. Fed. Proc. 21, 283 (1962).
Korey, S. R., and A. Stein: A Gangliosidase System. Brain lipids and lipoproteins and the leucodystrophies, p. 71. Amsterdam: Elsevier 1963a.
Korey, S. R., and A. Stein, and J. Gonatas: Separation of human brain glycolipids. Life Sciences 5, 296 (1963b).
Korey, S. R, and A. Stein: Studies on Tay-Sachs disease. III. Biochemistry. A. Analytic and metabolic aspects. J. Neuropath, exp. Neurol. 22, 56 (1963c).
Korey, S. R, and A. Stein, A. Stein : Studies in Tay-Sachs diseases. III. Biochemistry. Catabolism of gangliosides and related compounds. J. Neuropath, exp. Neurol. 22, 67 (1963d).
Kuhn, R., H. Egge, R. Brossmer, A. Gauche, P. Klesse, W. Lochinger, E. Rohm, u. H. Trischmann: Über die Ganglioside des Gehirns. Angew. Chemie 72, 805 (1960).
Kuhn, R., H. Egge: Über Ergebnisse der Permethylierung der Ganglioside Gì and Gn. Chem. Ber. 96, 3338 (1963c).
Kuhn, R., H. Egge u. H. Weigandt: Die Konstitution der Ganglio-N-Tetraose und des Gangliosids G1.Chem. Ber. 96, 866 (1963a).
Kuhn, R., H. Egge u. H. Weigandt: Die Konstitution der Ganglioside Gn, Gm, und Giv. Z. Naturforsch. 18 b, 541 (1963).
Kuhn, R., H. Egge u. H. Weigandt: Weitere Ganglioside aus Menschenhirn. Z. Naturforsch. 19 b, 256 (1964).
Kunan, W. H. : Über die Struktur von zwei hexosaminhaltigen Gangliosiden aus menschlichem Gehirn. Dissertation Köln 1964.
Landing, B. H.: Familial Neuroviceral Lipidosis. Amer. J. Dis. Child. 108, 503 (1964).
Landing, B. H., and J. H. Rubenstein: Biopsy diagnosis of neurological diseases in childhood with emphasis on lipidosis. In S. M. Aron son and B. W. Volk (Editors): Cerebral Sphingolipidoses p. 1. New York: Academic Press 1962.
Land Steiner, K., and P. A. Le vene: Observations on the specific part of the heterogenetic antigen. J. Immunol. 10, 731 (1925).
Lees, M. B., and H. W. Moser: The chemical pathology of Krabbe Disease and Metachromatic Leucodystrophy. In S. M. Aronson, and B. W. Volk (Editors) : Cerebral Sphingolipidosis, p. 179. New York: Academic Press, 1962.
Leloir, L. F., and C. E. Cardini: Enzymes acting on glucosamine phosphates. Biochim. biophys. Acta (Amst.) 20, 33 (1956).
Levene, P. A., and C. J. West: On sphingosine. III. The oxidation of sphingosine and dihy-drosphingosine. J. biol. Chem. 18, 481 (1914.)
Makita, A., and T. Yamakawa: The glycolipids of the brain of Tay-Sachs disease. The chemical structures of a globoside and main ganglioside. Jap. J. exp. Med. 33, 361 (1963).
Maley, G. F., and H. A. Lardy: The synthesis of a-D-glucosamine-1 -phosphate and N-acetyl-a-D-glucosamine-1 -phosphate. Enzymatic formation of uridine diphosphogluco-samine. J. Amer. chem. Soc. 78, 5303 (1956).
Marinetti, G., and E. Stotz: Studies on the structure of sphingomyelin IV. Configuration of the double bond in sphingomyelin and related lipids and a study of their infrared spectra. J. Amer. chem. Soc. 76,1347 (1954).
McKhann, G. M., R. Levy, and W. Ho: Biosynthesis of Sulfatides in Rat Brain. Fed. Proc. 24, 360 (1965).
Mehl, E., u. H. Jatzkewitz: Über ein Cerebrosid-Schwefelsäureester spaltendes Enzym aus Schweineniere. Sonderdruck Hoppe-Seylers Z. physiol. Chem. 331, 292 (1963).
Mislow, K.: The geometry of sphingosine. J. Amer. chem. Soc. 74, 5155 (1953).
Morozova, M. S., and M. Promyslov: On the problem of enzymatic splitting of cerebrosides of the brain. Bull. exp. biol. Med. (USSR.) 50, 44 (1960).
Moser, H. W., and M. L. Karnovsky: Studies on the biosynthesis of glycolipids and other lipids of the brain. J. biol. Chem. 234, 1990 (1959).
Mueller, K. L.: Thesis, Master of Science, University of Illinois 1953.
Norman, R. M. : Tay-Sachs Disease with visceral involvement and its relationship to Niemann-Pick’s disease, J. Path. Bact. 78, 409 (1959).
O’Brien, J. S. : A molecular defect of myelination. Biochem. biophys. Res. Commun. 15, 484 (1964).
O’Brien, J. S. , M. B. Stern, B. H. Landing, J. K. O’Brien, and G. N. Donnell: Generalized Gangliosidosis. Amer. J. Dis. Child. 109, 338 (1965).
Oda, T.: Components of penicillin-producing moulds. II. Fungus cerebrin. Pharm. Soc. jap. 72, 136, 139, 142 (1952).
Pilz, H., u. H. Jatzkewitz: Dünnschichtchromatographische Bestimmungen von C-18 und C24-Sphingomyelm in normalen und pathologischen Gehirnen einschließlich eines Falles von Niemann-Pickscher Erkrankung. J. Neurochem. 11, 603 (1964)
Pogell, B. M., and R. Gryder: Enzymatic synthesis of glucosamine 6-phosphate in rat liver. J. biol. Chem. 228. 701 (1957).
Prostenik, M., and N. Z. Stanacev: Studies in the series of sphingolipids. X. The structure of yeast cerebrin base. Chem. Ber. 91. 961 (1958).
Prostenik, M., and N. Z. Stanacev and B. Majhofer-Orescanin: Occurrence of a new sphingolipid base C20-sphingosine in horse and beef brain. Naturwissenschaften 47, 399 (1960).
Ptjtman, E. W., and W. Z. Hassid: Structure of galactosylglycerol from Irideae laminarioides. J. Amer. chem. Soc. 76, 2221 (1954).
Radin, N. S., F. B. Lavin, and J. R. Brown: Determination of cerebrosides. J. biol. Chem. 217. 789 (1955).
Radin, N. S., F. B. Martin, and J. R. Brown: Galactolipid metabolism. J. biol. Chem. 224, 499 (1957).
Rapport, M. M., L. Graf, L. A. Atttilio, and W. T. Norton: Immunochemical studies of organ and tumor lipids: XIV. Galactocerebroside determinants in the myelin sheath of the central nervous system. J. Neurochem. 11, 855 (1964).
Rapport, M. M., L. Grafand N. F. Alonzo : Immunochemical studies of organ and tumor lipids: VIII. Comparison of human tumor and ox spleen cvtosides. J. Lipid Res. 1, 301 (1960).
Rapport, M. M.,V. P. Skipski, and N. F. Alonzo : Cvtolipin H, a pure lipid hapten isolated from human carcinoma. Nature (Lond.) 181. 1803 (1958).
Rapport, M. M.,V. P. Skipski, and J. Yartv: Immunochemical studies of organ and tumor lipids: IX. Configuration of the carbohydrate residues in cvtolipin H. Arch. Biochem. 92, 438 (1961a).
Rapport, M. M., V. P. Skipski, and C. C. Sweeley: The lipid residues in cvtolipin H. J. Lipid Res. 2,148 (1961b).
Robbins, P. W., and F. Lipmann: The enzvmatic sequence in the biosynthesis of active sulfate. J. Amer. chem. Soc. 78, 6409 (1956).
Robbins, P. W., and F. Lipmann: Separation of the two enzymatic phases in active sulfate synthesis. J. biol. Chem. 233, 681 (1958a).
Robbins, P. W., and F. Lipmann: Enzymatic synthesis of adenosine-5′-phosphosulfate. J. biol. Chem. 233, 686 (1958b).
Roseman, S.: Enzymatic svnthesis of cytidine-5′-monophosphozialic acids. Proc. nat. Acad. Sci. (Wash.) 48, 437 (1962).
Rosenberg, A., and N. Stern: Changes in the lipid components of the gangliosides of developing brain. Fed. Proc. 24. 360 (1965).
Sambastvarao, K., and R. H. McCltjer: Lipid components of gangliosides. J. Lipid Res. 5, 103 (1964).
Sammartino, V.: Über die Chemie der Lunge. I. Mitteilung. Biochem. Z. 124, 234 (1921).
Sandhoff, K., H. Pilzu. H. Jatzkewitz: Über den enzymatischen Abbau von N-acetyl-neuraminsäurefreien Gangliosidresten (Ceramid-Oligosacchariden). Hoppe-Seylers Z. phy-siol. Chem. 338, 281 (1964).
Scheinberg, L. C, M. W. Kies, and E. C. Alvord jr. : Research in Demyelinating Diseases. Ann. N. Y. Acad. Sci. 122, 1–570 (1965).
Schmitz, H., V. R. Potter, R. B. Htjrlbert, and D. M. White: Alternative pathways of glucose metabolism. II. Nucleotides from the acid soluble fraction of normal and tumor tissues and studies on nucleic acid synthesis in tumors. Cancer Res. 14, 66 (1954).
Soda, T.: in S. Akabori, ed., Textbook of Enzymological Methods II. 73 (1956). Tokyo: Asakura Press.
Somers, J. E., J. N. Kanfer, and R. O. Brady: Immunochemical studies with gangliosides. II. Investigations of the structure of gangliosides by the hapten inhibition technique. Biochemistry 3, 251 (1964).
Sotjrander, P., and L. Svennerholm: Sulphatide lipidosis in the adult with the clinical picture of progressive organic dementia with epileptic seizures. Acta neuropath. (Beri.) 1, 384 (1962).
Sprinson, D. B., and A. Cotjlon: The precursors of sphingosine in brain tissue. J. biol. Chem. 207, 585 (1954).
Sribney, M., and E. P. Kennedy: The enzymatic synthesis of sphingomyelin. J. biol. Chem. 233. 1315 (1958).
Stanacev, N. Z., and E. Chargaff: Icosisphingosine, a long chain base constituent of muco-lipids. Biochem. biophys. Acta (Amst.) 59, 733 (1962).
Stanbtjry, J. B.. and D. S. Fredrickson: The metabolic basis of inherited disease. New York: McGraw Hill Book Co. 1960.
Stodola, F. H., and L. J. Wickerham: Formation of extracellular sphingolipids by microorganisms. II. Structural studies on tetraacetylphytosphingosine from the yeast Hansenula ciferrii. J. biol. Chem. 235, 2584 (1960).
Stodola, F. H., C. R. Scholfteld, and H.J. Dutton: Formation of extracellular sphingolipids by microorganisms. II. Triacetyl dihydrosphingosine, a metabolic product of the yeast Hansenula ciferrii. Arch. Biochem. 98, 176 (1962)
Stoffyn P., and A. Stoffyn: Structure of sulfatides. Biochem. biophys. Acta (Amst.) 70, 218 (1963).
Strominger, J. L. : Uridine diphosphate acetylglucosamine phosphate and uridine diphosphate acetylglucosamine sulfate. Biochem. biophys. Acta (Amst.) 17, 283 (1955).
Suomi, W. D., and B. W. Agranoff: Identification and estimation of glycolipids of the spleen in Gauchers’ disease. Fed. Proc. 23, 375 (1964).
Suzuki, K. : Incorporation of D-glucose-U-C14 into gangliosides in a cell-free system. Biochem. biophys. Kes. Commun. 16, 88 (1964).
Suzuki, K. , and S. R. Korey: Incorporation of D-(C14) glucose into individual gangliosides. Biochem. biophys. Acta (Amst.) 78, 388 (1963).
Svennerholm, L.: The chemical structure of normal human brain and Tay-Sachs gangliosides. Biochem. biophys. Res. Commun. 9, 436 (1962).
Svennerholm, L.: Chromatographic separation of human brain gangliosides. J. Neurochem. 10, 613 (1963).
Sweeley, C. C, and B. Klionsky : Fabry’s disease : Classification as a sphingolipidosis and partial characterization of a novel glycolipid. J. biol. Chem. 238, 3148 (1963).
Taketomi T., and T. Yamakawa: Immunochemical studies on lipids. I. Preparation and immunochemical properties of synthetic psychosine-protein antigens. J. Biochem. (Tokyo) 54, 444 (1963).
Taketomi, T., and T. Yamakawa: Further confirmation on the structure of brain cerebroside sulfuric ester. J. Biochem. (Tokyo) 55, 87 (1964).
Taketomi, T., and T. Yamakawa: Aiitigenic properties of synthetic protein complexes with glycolipids and related substances. Abstract, American Oil Chemists Society Symposium on Glycolipids and the Nervous System 1965.
Thannhauser, S. J., and M. Reichel: Studies on animal lipids. X. The nature of cerebrosi-dase. Its relation to the splitting of polydiaminophosphatide by polydiaminophosphatase. J. biol. Chem. 113, 311 (1936).
Thudicum, J. W. L.: A treatise on the chemical composition of the brain. London: Builliere, Tindall, and Cox 1884.
Trams, E. G., and C. J. Lauter: On the isolation and characterization of gangliosides. Biochem. biophys. Acta (Amst.) 60, 350 (1962).
van Bogaert, L., J. N. Cumming, and A. Lowenthal (Editors) : Cerebral Lipidosis. Springfield (Ill.): Thomas 1957.
Volk, B. W., and W. D. Sperry(Editors) : Symposium on Amaurotic Family Idiocy. Amer. J. Dis. Child. 97, 655 (1959).
Warren, L., and H. Felsenfeld: N-acetylmannosamine-6-phosphate on N-acetylneuraminic acid-9-phosphate as intermediates in sialic acid biosynthesis. Biochem. biophys. Res. Commun. 5, 185 (1961).
Warren, L., and H. Felsenfeld: The biosynthesis of sialic acids. J. biol. Chem. 237, 1421 (1962).
Weiss, S. B., and E. P. Kennedy: The function of cytidine coenzymes in the biosynthesis of phospholipids. J. biol. Chem. 222, 193 (1956).
Wickerham, L. J., and F. H. Stodola: Formation of extracellular sphingolipids by microorganisms. J. Bact. 80, 484 (1960).
Williams, H. H., H. Galbraith, M. Kancher, E. Z. Moyer, A. J. Richards, and I. G. Macy: The effect of growth on the lipid composition of rat tissues. J. biol. Chem. 161, 475 (1945).
Wdlson, L. G., and R. S. Bandurski: An enzymatic reaction involving adenosine triphosphate and selenate. Arch. Biochem. 62, 503 (1956).
Wdlson, L. G., and R. S. Bandurski: Enzymatic reactions involving sulfate, sulfite, selenate, and molybdate. J. biol. Chem. 233, 975 (1958).
Wittenberg, J. B.: In S. R. Korey (Editor): The Biology of Myelin, p. 296. New York: Hoeber-Harper Book 1959.
Yamakawa, T., N. Kiso, S. Handa, A. Makita, and S. Yokoyama: On the structure of brain cerebroside sulfuric ester and ceramide dihexoside of erythrocytes. J. Biochem. 52, 226 (1962).
Yokoyama, M., E. G. Trams, and R. O. Brady: Sphingolipid antibodies in sera of animals and patients with central nervous system lesions. J. Immunol. 90, 372 (1963).
Zabin, I. : Biosynthesis of ceramide by rat-brain homogenates. J. Amer. chem. Soc. 79, 5834 (1957).
Zabin, I.,and J. F. Mead: The biosynthesis of sphingosine. J. biol. Chem. 205, 271 (1953).
Zabin, I.,and J. F. Mead: The biosynthesis of sphingosine. II. The utilization of methyl-labeled acetate, formate, and ethanolamine, J. biol. Chem. 211, 87 (1954).
Editor information
Rights and permissions
Copyright information
© 1967 Springer-Verlag Berlin · Heidelberg
About this chapter
Cite this chapter
Burton, R.M. (1967). Biochemistry of Sphingosine Containing Lipids. In: Schettler, G. (eds) Lipids and Lipidoses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-87367-6_5
Download citation
DOI: https://doi.org/10.1007/978-3-642-87367-6_5
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-87369-0
Online ISBN: 978-3-642-87367-6
eBook Packages: Springer Book Archive