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Volumn 40, Issue 5, 1999, Pages 839-849

Structure and properties of totally synthetic galacto- and gluco- cerebrosides

Author keywords

Differential scanning calorimetry; Glycolipids; Hydrocarbon chain packing; Hydrogen bonding; Lipid bilayers; X ray diffraction

Indexed keywords

GALACTOSYLCERAMIDASE; GLUCOSYLCERAMIDASE; GLYCOLIPID;

EID: 0032945569     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (53)

References (51)
  • 2
    • 0026475989 scopus 로고
    • The gp120 glycoprotein of HIV-1 binds to sulfatide and to myelin associated glycoprotein
    • van den Berg, L. H., S. A. Sadiq, S. Lederman, and N. Latov. 1992. The gp120 glycoprotein of HIV-1 binds to sulfatide and to myelin associated glycoprotein. J. Neurosci. Res. 33: 513-518.
    • (1992) J. Neurosci. Res. , vol.33 , pp. 513-518
    • Van Den Berg, L.H.1    Sadiq, S.A.2    Lederman, S.3    Latov, N.4
  • 3
    • 0027489512 scopus 로고
    • Gangliosides as receptors for bacterial enterotoxins
    • Fishman, P. H., T. Pacuszka, and P. A. Orlandi. 1993. Gangliosides as receptors for bacterial enterotoxins. Adv. Lipid Res. 25: 165-187.
    • (1993) Adv. Lipid Res. , vol.25 , pp. 165-187
    • Fishman, P.H.1    Pacuszka, T.2    Orlandi, P.A.3
  • 4
    • 0029664655 scopus 로고    scopus 로고
    • M1 in phosphatidylcholine bilayer membranes
    • M1 in phosphatidylcholine bilayer membranes. Biophys. J. 70: 1363-1372.
    • (1996) Biophys. J. , vol.70 , pp. 1363-1372
    • Reed, R.A.1    Shipley, G.G.2
  • 8
    • 0014202481 scopus 로고
    • Structure of liquid-crystalline phases of different phospholipids, monoglycerides and sphingolipids in the absence and presence of water
    • Reiss-Husson, F. 1967. Structure of liquid-crystalline phases of different phospholipids, monoglycerides and sphingolipids in the absence and presence of water. J. Mol. Biol. 25: 363-382.
    • (1967) J. Mol. Biol. , vol.25 , pp. 363-382
    • Reiss-Husson, F.1
  • 9
    • 0020481595 scopus 로고
    • Thermal behavior of fractionated and unfractionated bovine brain cerebrosides
    • Curatolo, W. 1982. Thermal behavior of fractionated and unfractionated bovine brain cerebrosides. Biochemistry. 21: 1761-1764.
    • (1982) Biochemistry , vol.21 , pp. 1761-1764
    • Curatolo, W.1
  • 10
    • 0017202110 scopus 로고
    • Molecular arrangements in sphingolipids. Conformation and hydrogen bonding of ceramide and their implication on membrane stability and permeability
    • Pascher, I. 1976. Molecular arrangements in sphingolipids. Conformation and hydrogen bonding of ceramide and their implication on membrane stability and permeability. Biochim. Biophys. Acta. 455: 433-451.
    • (1976) Biochim. Biophys. Acta. , vol.455 , pp. 433-451
    • Pascher, I.1
  • 11
    • 0017636970 scopus 로고
    • Molecular arrangements of sphingolipids. The monolayer behavior of ceramides
    • Lofgren, H., and I. Pascher. 1977. Molecular arrangements of sphingolipids. The monolayer behavior of ceramides. Chem. Phys. Lipids. 20: 273-284.
    • (1977) Chem. Phys. Lipids. , vol.20 , pp. 273-284
    • Lofgren, H.1    Pascher, I.2
  • 12
    • 0000764022 scopus 로고
    • Molecular arrangement in sphingolipids. The crystal structure of cerebroside
    • Pascher, I., and S. Sundell. 1977. Molecular arrangement in sphingolipids. The crystal structure of cerebroside. Chem. Phys. Lipids. 20: 175-191.
    • (1977) Chem. Phys. Lipids. , vol.20 , pp. 175-191
    • Pascher, I.1    Sundell, S.2
  • 13
    • 0018803540 scopus 로고
    • Two gel states of cerebrosides: Calorimetric and Raman spectroscopic evidence
    • Bunow, M. R. 1979. Two gel states of cerebrosides: calorimetric and Raman spectroscopic evidence. Biochim. Biophys. Acta. 574: 542-546.
    • (1979) Biochim. Biophys. Acta. , vol.574 , pp. 542-546
    • Bunow, M.R.1
  • 14
    • 0019210914 scopus 로고
    • Molecular conformations of cerebrosides in bilayers determined by Raman spectroscopy
    • Bunow, M. R., and I. W. Levin. 1980. Molecular conformations of cerebrosides in bilayers determined by Raman spectroscopy. Biophys. J. 32: 1007-1021.
    • (1980) Biophys. J. , vol.32 , pp. 1007-1021
    • Bunow, M.R.1    Levin, I.W.2
  • 15
    • 0019879359 scopus 로고
    • X-ray diffraction and calorimetric study of anhydrous and hydrated N-palmitoylgalactosylsphingosine (cerebroside)
    • Ruocco, M. J., D. Atkinson, D. M. Small, R. P. Skarjune, E. Oldfield, and G. G. Shipley. 1981. X-ray diffraction and calorimetric study of anhydrous and hydrated N-palmitoylgalactosylsphingosine (cerebroside). Biochemistry. 21: 5957-5966.
    • (1981) Biochemistry , vol.21 , pp. 5957-5966
    • Ruocco, M.J.1    Atkinson, D.2    Small, D.M.3    Skarjune, R.P.4    Oldfield, E.5    Shipley, G.G.6
  • 16
    • 0020791847 scopus 로고
    • Galactocerebroside-phospholipid interactions in bilayer membranes
    • Ruocco, M. J., G. G. Shipley, and E. Oldfield. 1983. Galactocerebroside-phospholipid interactions in bilayer membranes. Biophys. J. 43: 91-101.
    • (1983) Biophys. J. , vol.43 , pp. 91-101
    • Ruocco, M.J.1    Shipley, G.G.2    Oldfield, E.3
  • 17
    • 0021098895 scopus 로고
    • Hydration of N-palmitoylgalactosylsphingosine compared to monosaccharide hydration
    • Ruocco, M. J., and G. G. Shipley. 1983. Hydration of N-palmitoylgalactosylsphingosine compared to monosaccharide hydration. Biochim. Biophys. Acta. 735: 305-308.
    • (1983) Biochim. Biophys. Acta. , vol.735 , pp. 305-308
    • Ruocco, M.J.1    Shipley, G.G.2
  • 18
    • 0021673932 scopus 로고
    • Interaction of cholesterol with galactocerebroside and galactocerebroside-phosphatidylcholine bilayer membranes
    • Ruocco, M. J., and G. G. Shipley. 1984. Interaction of cholesterol with galactocerebroside and galactocerebroside-phosphatidylcholine bilayer membranes. Biophys. J. 46: 695-707.
    • (1984) Biophys. J. , vol.46 , pp. 695-707
    • Ruocco, M.J.1    Shipley, G.G.2
  • 19
    • 0022356526 scopus 로고
    • Phase behavior of galactocerebrosides from bovine brain
    • Curatolo, W., and F. B. Jungalwala. 1985. Phase behavior of galactocerebrosides from bovine brain. Biochemistry. 24: 6608-6613.
    • (1985) Biochemistry , vol.24 , pp. 6608-6613
    • Curatolo, W.1    Jungalwala, F.B.2
  • 20
    • 0023116552 scopus 로고
    • Structure and metastability of N-lignocerylgalactosylsphingosine (cerebroside) bilayers
    • Reed, R. A., and G. G. Shipley. 1987. Structure and metastability of N-lignocerylgalactosylsphingosine (cerebroside) bilayers. Biochim. Biophys. Acta. 896: 153-164.
    • (1987) Biochim. Biophys. Acta. , vol.896 , pp. 153-164
    • Reed, R.A.1    Shipley, G.G.2
  • 21
    • 0023876780 scopus 로고
    • Phase behavior of cerebroside and its fractions with phosphatidylcholines: Calorimetric studies
    • Bunow, M. R., and I. W. Levin. 1988. Phase behavior of cerebroside and its fractions with phosphatidylcholines: calorimetric studies. Biochim. Biophys. Acta. 939: 577-586.
    • (1988) Biochim. Biophys. Acta. , vol.939 , pp. 577-586
    • Bunow, M.R.1    Levin, I.W.2
  • 22
    • 0023947258 scopus 로고
    • A calorimetric study of the thermotropic behaviour of mixtures of brain cerebrosides with other brain lipids
    • Johnston, D. S., and D. Chapman. 1988. A calorimetric study of the thermotropic behaviour of mixtures of brain cerebrosides with other brain lipids. Biochim. Biophys. Acta. 939: 603-614.
    • (1988) Biochim. Biophys. Acta. , vol.939 , pp. 603-614
    • Johnston, D.S.1    Chapman, D.2
  • 23
    • 0023708349 scopus 로고
    • Differential scanning calorimetric and Fourier transform infrared spectroscopic investigations of cerebroside polymorphism
    • Jackson, M., D. S. Johnston, and D. Chapman. 1988. Differential scanning calorimetric and Fourier transform infrared spectroscopic investigations of cerebroside polymorphism. Biochim. Biophys. Acta. 944: 497-506.
    • (1988) Biochim. Biophys. Acta. , vol.944 , pp. 497-506
    • Jackson, M.1    Johnston, D.S.2    Chapman, D.3
  • 24
    • 0024501591 scopus 로고
    • Effect of chain unsaturation on the structure and thermotropic properties of galactocerebrosides
    • Reed, R. A., and G. G. Shipley. 1989. Effect of chain unsaturation on the structure and thermotropic properties of galactocerebrosides. Biophys. J. 55: 281-292.
    • (1989) Biophys. J. , vol.55 , pp. 281-292
    • Reed, R.A.1    Shipley, G.G.2
  • 25
    • 0026341957 scopus 로고
    • Structural determinants of miscibility in surface films of galactosylceramide and phosphatidylcholine: Effect of unsaturation in the galactosylceramide acyl chain
    • Ali, S., H. L. Brockman, and R. E. Brown. 1991. Structural determinants of miscibility in surface films of galactosylceramide and phosphatidylcholine: effect of unsaturation in the galactosylceramide acyl chain. Biochemistry. 30: 11198-11205.
    • (1991) Biochemistry , vol.30 , pp. 11198-11205
    • Ali, S.1    Brockman, H.L.2    Brown, R.E.3
  • 26
    • 0027440955 scopus 로고
    • Acyl structure regulates galactosylceramide's interfacial interactions
    • Ali, S., J. M. Smaby, and R. E. Brown. 1993. Acyl structure regulates galactosylceramide's interfacial interactions. Biochemistry. 32: 11696-11703.
    • (1993) Biochemistry , vol.32 , pp. 11696-11703
    • Ali, S.1    Smaby, J.M.2    Brown, R.E.3
  • 27
    • 0028214986 scopus 로고
    • Cholesterol's interfacial interactions with galactosylceramides
    • Ali, S., J. M. Smaby, H. L. Brockman, and R. E Brown. 1994. Cholesterol's interfacial interactions with galactosylceramides. Biochemistry. 33: 2900-2906.
    • (1994) Biochemistry , vol.33 , pp. 2900-2906
    • Ali, S.1    Smaby, J.M.2    Brockman, H.L.3    Brown, R.E.4
  • 28
    • 0029610195 scopus 로고
    • Structure and properties of N-palmitoleoyl-galactosylsphingosine (cerebroside)
    • Haas, N. S., and G. G. Shipley. 1995. Structure and properties of N-palmitoleoyl-galactosylsphingosine (cerebroside). Biochim. Biophys. Acta. 1240: 133-141.
    • (1995) Biochim. Biophys. Acta. , vol.1240 , pp. 133-141
    • Haas, N.S.1    Shipley, G.G.2
  • 29
    • 0019317537 scopus 로고
    • Calorimetric investigation of the complex phase behavior of glucocerebroside dispersions
    • Freire, E., D. Bach, M. Correa-Freire, I. Miller, and Y. Barenholz. 1980. Calorimetric investigation of the complex phase behavior of glucocerebroside dispersions. Biochemistry. 19: 3662-3665.
    • (1980) Biochemistry , vol.19 , pp. 3662-3665
    • Freire, E.1    Bach, D.2    Correa-Freire, M.3    Miller, I.4    Barenholz, Y.5
  • 30
    • 0026650348 scopus 로고
    • Calorimetric and X-ray diffraction studies of rye glucocerebroside
    • Lynch, D. V., M. Caffrey, J. L. Hogan, and P. L. Steponkus. 1992. Calorimetric and X-ray diffraction studies of rye glucocerebroside. Biophys. J. 61: 1289-1300.
    • (1992) Biophys. J. , vol.61 , pp. 1289-1300
    • Lynch, D.V.1    Caffrey, M.2    Hogan, J.L.3    Steponkus, P.L.4
  • 31
    • 0019956308 scopus 로고
    • Physical studies of cell surface and cell membrane structure. Deuterium magnetic resonance studies of N-palmitoylglucosylceramide (cerebroside) head group structure
    • Skarjune, R., and E. Oldfield. 1982. Physical studies of cell surface and cell membrane structure. Deuterium magnetic resonance studies of N-palmitoylglucosylceramide (cerebroside) head group structure. Biochemistry. 21: 3154-3160.
    • (1982) Biochemistry , vol.21 , pp. 3154-3160
    • Skarjune, R.1    Oldfield, E.2
  • 32
    • 0021004876 scopus 로고
    • Partial synthesis and physical properties of cerebroside sulfate containing palmitic acid or alpha-hydroxy palmitic acid
    • Koshy, K. M., and J. M. Boggs. 1983. Partial synthesis and physical properties of cerebroside sulfate containing palmitic acid or alpha-hydroxy palmitic acid. Chem. Phys. Lipids. 34: 41-53.
    • (1983) Chem. Phys. Lipids. , vol.34 , pp. 41-53
    • Koshy, K.M.1    Boggs, J.M.2
  • 33
    • 0021714034 scopus 로고
    • Effect of fatty acid chain length, fatty acid hydroxylation, and various cations on the behavior of synthetic cerebroside sulfate
    • Boggs, J. M., K. M. Koshy, and G. Rangaraj. 1984. Effect of fatty acid chain length, fatty acid hydroxylation, and various cations on the behavior of synthetic cerebroside sulfate. Chem. Phys. Lipids. 36: 65-89.
    • (1984) Chem. Phys. Lipids. , vol.36 , pp. 65-89
    • Boggs, J.M.1    Koshy, K.M.2    Rangaraj, G.3
  • 34
    • 0024276668 scopus 로고
    • Influence of structural modifications on the phase behavior of semi-synthetic cerebroside sulfate
    • Boggs, J. M., K. M. Koshy, and G. Rangaraj. 1988. Influence of structural modifications on the phase behavior of semi-synthetic cerebroside sulfate. Biochim. Biophys. Acta. 938: 361-372.
    • (1988) Biochim. Biophys. Acta. , vol.938 , pp. 361-372
    • Boggs, J.M.1    Koshy, K.M.2    Rangaraj, G.3
  • 35
    • 0024276685 scopus 로고
    • Interdigitated lipid bilayers of long acyl chain species of cerebroside sulfate. A fatty acid spin label study
    • Boggs, J. M., K. M. Koshy, and G. Rangaraj. 1988. Interdigitated lipid bilayers of long acyl chain species of cerebroside sulfate. A fatty acid spin label study. Biochim. Biophys. Acta. 938: 373-385.
    • (1988) Biochim. Biophys. Acta. , vol.938 , pp. 373-385
    • Boggs, J.M.1    Koshy, K.M.2    Rangaraj, G.3
  • 37
    • 0022636075 scopus 로고
    • New methods for the synthesis of glycosides and oligosaccharides. Are there alternatives to the Koenigs-Knorr method?
    • Schmidt, R. R. 1986. New methods for the synthesis of glycosides and oligosaccharides. Are there alternatives to the Koenigs-Knorr method? Angew. Chem. Int. Ed. Engl. 25: 212-235.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 212-235
    • Schmidt, R.R.1
  • 38
    • 84985610035 scopus 로고
    • Synthesis of glycosphingolipids and psychosines
    • Schmidt, R. R., and P. Zimmermann. 1986. Synthesis of glycosphingolipids and psychosines. Angew. Chem. Int. Ed. Engl. 25: 725-726.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 725-726
    • Schmidt, R.R.1    Zimmermann, P.2
  • 39
    • 0347756774 scopus 로고
    • Synthesis of D-erythrosphingosines
    • Schmidt, R. R., and P. Zimmermann. 1986. Synthesis of D-erythrosphingosines. Tetrahedron Lett. 27: 481-484.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 481-484
    • Schmidt, R.R.1    Zimmermann, P.2
  • 40
  • 41
    • 0025883137 scopus 로고
    • Stereochemistry and size of sugar headgroups determine structure and phase behavior of glycolipid membranes: Densitometric, calorimetric and X-ray studies
    • Hinz, H-J., H. Kuttenreich, R. Meyer, M. Renner, R. Frund, R. Koynova, A. I. Boyanov, and B. G. Tenchov. 1991. Stereochemistry and size of sugar headgroups determine structure and phase behavior of glycolipid membranes: densitometric, calorimetric and X-ray studies. Biochemistry. 30: 5125-5138.
    • (1991) Biochemistry , vol.30 , pp. 5125-5138
    • Hinz, H.-J.1    Kuttenreich, H.2    Meyer, R.3    Renner, M.4    Frund, R.5    Koynova, R.6    Boyanov, A.I.7    Tenchov, B.G.8
  • 42
    • 0022434003 scopus 로고
    • Head-group contributions to bilayer stability: Monolayer and calorimetric studies on synthetic, stereochemically uniform glucolipids
    • Hinz, H-J., L. Six, K-P. Reuss, and M. Lieflander. 1985. Head-group contributions to bilayer stability: monolayer and calorimetric studies on synthetic, stereochemically uniform glucolipids. Biochemistry. 24: 806-813.
    • (1985) Biochemistry , vol.24 , pp. 806-813
    • Hinz, H.-J.1    Six, L.2    Reuss, K.-P.3    Lieflander, M.4
  • 44
    • 0024298853 scopus 로고
    • Influence of head-group interactions on the miscibility of synthetic stereochemically pure glycolipids and phospholipids
    • Koynova, R. D., H. L. Kuttenreich, B. G. Tenchov, and H-J. Hinz. 1988. Influence of head-group interactions on the miscibility of synthetic stereochemically pure glycolipids and phospholipids. Biochemistry. 27: 4612-4619.
    • (1988) Biochemistry , vol.27 , pp. 4612-4619
    • Koynova, R.D.1    Kuttenreich, H.L.2    Tenchov, B.G.3    Hinz, H.-J.4
  • 45
    • 0023800018 scopus 로고
    • The physical properties of glycosyl diacylglycerols. Calorimetric studies of a homologous series of 1,2-di-O-acyl-3-O-(β-D-glucopyranosyl)-sn-glycerols
    • Mannock, D. A., R. N. A. H. Lewis, A. Sen, and R. N. McElhaney. 1988. The physical properties of glycosyl diacylglycerols. Calorimetric studies of a homologous series of 1,2-di-O-acyl-3-O-(β-D-glucopyranosyl)-sn-glycerols. Biochemistry. 27: 6852-6859.
    • (1988) Biochemistry , vol.27 , pp. 6852-6859
    • Mannock, D.A.1    Lewis, R.N.A.H.2    Sen, A.3    McElhaney, R.N.4
  • 46
    • 0025164471 scopus 로고
    • The physical properties of glycosyl diacylglycerols. 1. Calorimetric studies of a homologous series of 1,2-di-O-acyl-3-O-(α-D-glucopyranosyl)-sn-glycerols
    • Mannock, D. A., R. N. A. H. Lewis, and R. N. McElhaney. 1990. The physical properties of glycosyl diacylglycerols. 1. Calorimetric studies of a homologous series of 1,2-di-O-acyl-3-O-(α-D-glucopyranosyl)-sn-glycerols. Biochemistry. 29: 7790-7799.
    • (1990) Biochemistry , vol.29 , pp. 7790-7799
    • Mannock, D.A.1    Lewis, R.N.A.H.2    McElhaney, R.N.3
  • 47
    • 0028218496 scopus 로고
    • Differential scanning calorimetry and x-ray diffraction studies the thermotropic phase behavior of the diastereomeric di-tetradecyl-β-D-galactosyl glycerols and their mixture
    • Mannock, D. A., R. N. McElhaney, P. E. Harper, and S. M. Gruner. 1994. Differential scanning calorimetry and x-ray diffraction studies the thermotropic phase behavior of the diastereomeric di-tetradecyl-β-D-galactosyl glycerols and their mixture. Biophys. J. 66: 734-740.
    • (1994) Biophys. J. , vol.66 , pp. 734-740
    • Mannock, D.A.1    McElhaney, R.N.2    Harper, P.E.3    Gruner, S.M.4
  • 48
    • 0025005039 scopus 로고
    • The physical properties of glycosyl diacylglycerols. 2. X-ray diffraction studies of a homologous series of 1,2-di-O-acyl-3-O-(α-D-glucopyranosyl)-sn-glycerols
    • Sen, A., S. Hui, D. A. Mannock, R. N. A. H. Lewis, and R. N. McElhaney. 1990. The physical properties of glycosyl diacylglycerols. 2. X-ray diffraction studies of a homologous series of 1,2-di-O-acyl-3-O-(α-D-glucopyranosyl)-sn-glycerols. Biochemistry. 29: 7799-7804.
    • (1990) Biochemistry. , vol.29 , pp. 7799-7804
    • Sen, A.1    Hui, S.2    Mannock, D.A.3    Lewis, R.N.A.H.4    McElhaney, R.N.5
  • 49
    • 0025007520 scopus 로고
    • Physical properties of glycosyldiacylglycerols. An infrared spectroscopic study of the gel phase polymorphism of 1,2-di-O-acyl-3-O-(β-D-glucopyranosyl)-sn-glycerols
    • Lewis, R. N. A. H., D. A. Mannock, R. N. McElhaney, P. T. T. Wong, and H. H. Mantsch. 1990. Physical properties of glycosyldiacylglycerols. An infrared spectroscopic study of the gel phase polymorphism of 1,2-di-O-acyl-3-O-(β-D-glucopyranosyl)-sn-glycerols. Biochemistry. 29: 8933-8943.
    • (1990) Biochemistry , vol.29 , pp. 8933-8943
    • Lewis, R.N.A.H.1    Mannock, D.A.2    McElhaney, R.N.3    Wong, P.T.T.4    Mantsch, H.H.5
  • 50
    • 0026271656 scopus 로고
    • Differential scanning calorimetry and X-ray diffraction studies of a series of synthetic β-D-galactosyl diacyglycerols
    • Mannock, D. A., and R. N. McElhaney. 1991. Differential scanning calorimetry and X-ray diffraction studies of a series of synthetic β-D-galactosyl diacyglycerols. Biochem. Cell Biol. 69: 863-867.
    • (1991) Biochem. Cell Biol. , vol.69 , pp. 863-867
    • Mannock, D.A.1    McElhaney, R.N.2
  • 51
    • 0029129260 scopus 로고
    • Structural and thermotropic properties of synthetic C16:0 (palmitoyl) ceramide: Effect of hydration
    • Shah, J., J. M. Atienza, R. I. Duclos, A. V. Rawlings, Z. Dong, and G. G. Shipley. 1995. Structural and thermotropic properties of synthetic C16:0 (palmitoyl) ceramide: effect of hydration. J. Lipid Res. 36: 1936-1944.
    • (1995) J. Lipid Res. , vol.36 , pp. 1936-1944
    • Shah, J.1    Atienza, J.M.2    Duclos, R.I.3    Rawlings, A.V.4    Dong, Z.5    Shipley, G.G.6


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