Conformation of sulfoquinovosyldiacylglycerol bound to a magnetically oriented membrane system

Biophysical Journal

Volumn 71, Issue 5, 1996, Pages 2573-2582

  Howard, Kathleen P ^a,b   Prestegard, James H ^a  

^a YALE UNIVERSITY   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCEROL;

ANISOTROPY; ARTICLE; CALCULATION; CELL MEMBRANE CONDUCTANCE; NUCLEAR MAGNETIC RESONANCE; PROTEIN CONFORMATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0029960499     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-3495(96)79449-3     Document Type: Article

References (56)

1. Allinger, N. L., and J. Kao. 1976. Molecular mechanics studies of sulfoxides. Tetrahedron. 32:529-536.
2. Aubin, Y., Y. Ito, J. C. Paulson, and J. H. Prestegard. 1993. Structure and dynamics of the sialic acid moiety of the GM3-ganglioside at the surface of a magnetically oriented membrane. Biochemistry. 32:13405-13413.
3. Auger, M., M. Van Calsteren, I. C. P. Smith, and H. C. Jarrell. 1990. Glycerolipids: common features of molecular motion in bilayers. Biochemistry. 29:5815-5821.
4. Barber, J., and K. Gounaris. 1986. What role does sulpholipid play within the thylakoid membrane? Photosynth. Res. 9:239-249.
5. Bax, A., R. H. Griffey, and B. L. Hawkins. 1983. Correlation of proton and nitrogen-15 chemical shifts by multiple quantum NMR. J. Magn. Res. 55:301-315.
6. 13C assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. J. Am. Chem. Soc. 108:2093-2094.
7. Benson, A., H. Daniel, and R. Wiser. 1959. A sulfolipid in plants. Proc. Nail. Acad. Sci. USA. 45:1582-1587.
8. Bodenhausen, G., and D. J. Ruben. 1980. Natural abundance nitrogen-15 NMR by enhanced heteronuclear spectroscopy. Chem. Phys. Lett. 69: 185-189.
9. 13C nuclear magnetic resonance. Biophys. J. 53:839-843.
10. 13C chemical shift anisotropy. Chem. Phys. Lett. 72:462-465.
11. 13C in solid dimethyl oxalate. J. Chem. Phys. 85:4199-4201.
12. Gordon, D., and S. Danishefsky. 1991. Synthesis of a cyanobacterial sulfolipid: conformation of its structure, stereochemistry and anti-HIV-1 activity. J. Am. Chem. Soc. 114:659-663.
13. 13C correlation experiments for carbon backbone assignments of enriched natural products. J. Magn. Res. B. 101:126-133.
14. Gounaris, K., and J. Barber. 1985. Isolation and characterisation of a photosystem II reaction centre lipoprotein complex. FEBS Lett. 188: 68-72.
15. Gustafson, K., J. Cardellina, R. Fuller, O. Weislow, R. Kiser, K. Snader, G. Patterson, and M. Boyd. 1989. AIDS-antiviral sulfolipids from cyanobacteria (blue-green algae). J. Natl. Cancer Inst. 81:1254-1258.
16. Hare, B. J., K. P. Howard, and J. H. Prestegard. 1993. Torsion angle analysis of glycolipid order at membrane surfaces. Biophys. J. 64: 392-398.
17. 13C NMR studies of wheat germ agglutinin interactions with N-acetylglucosamine at a magnetically oriented bilayer surface. Biochemistry. 33: 10137-10148.
18. Harris, R. 1983. Nuclear Magnetic Resonance Spectroscopy. John Wiley, New York.
19. Harwood, J. 1980. Sulfolipids. In The Biochemistry of Plants. P. Stumpf, editor. Academic Press, New York. 301-320.
20. Howard, K., and J. Prestegard. 1995. Membrane and solution conformations of monogalactosyldiacylglycerol using NMR/molecular modeling methods. J. Am. Chem. Soc. 117:5031-5040.
21. Howard, K., and J. Prestegard. 1996. NMR studies of the conformation and dynamics of membrane-bound digalactosyldiacylglycerol. J. Am. Chem. Soc. 118:3345-3353.
22. 2H NMR of oriented multibilayers. Biochemistry. 26: 1805-1811.
23. Jeffrey, G. A., and R. Taylor. 1980. The application of molecular mechanics to the structures of carbohydrates. J. Comp. Chem. 1:99-109.
24. 13C chemical shifts and longitudinal relaxation times of 1,2-diacyl-3-(6-sulphoquinovosyl)sn-glycerol. Aust. J. Chem. 31:65-72.
25. Kogelberg, H., and T. J. Ruitherford. 1994. Studies on the three-dimensional behavior of the selectin ligands Lewis(a) and sulfated Lewis(a) using NMR spectroscopy and molecular dynmaics simulation. Glycobiology. 4:49-57.
26. Lamba, D., S. Glover, W. Mackie, A. Rashid, B. Sheldrick, and S. Perez. 1994. Insights into stereochemical features of sulphated carbohydrates: X-ray crystallographic and modelling investigations. Glycobiology. 4:151-163.
27. Mareci, T. H., and R. Freeman. 1982. Echoes and antiechoes in coherence transfer NMR: determining the signs of double-quantum frequencies. J. Magn. Res. 48:158-163.
28. McAlarney, T., S. Apostolski, S. Lederman, and N. Latov. 1994. Characteristics of HIV-1 gp120 glycoprotein binding to glycolipids. J. Neurosci. Res. 37:453-460.
29. McClure, M., J. Moore, D. Blanc, P. Scotting, G. Cook, R. Keynes, J. Weber, D. Davies, and R. Weiss. 1992. Investigations into the mechanism by which sulfated polysaccharides inhibit HIV infection in vitro. AIDS Res. Hum. Retroviruses. 8:19-26.
30. Nyholm, P., and I. Pascher. 1993. Orientation of the saccharide chains of glycolipids at the membrane surface: conformational analysis of the glucose-ceramide and the glucose-glyceride linkages using molecular mechanics (MM3). Biochemistry. 32:1225-1234.
31. Okaya, Y. 1964. The plant sulfolipid: a crystallographic study. Acta. Crystallogr. 17:1276-1282.
32. Pascher, I., M. Lundmark, P. Nyholm, and S. Sundell. 1992. Crystal structures of membrane lipids. Biochim. Biophys. Acta. 1113:339-373.
33. Pearson, R. H., and I. Pascher. 1979. The molecular structure of lecithin dihydrate. Nature. 281:499-501.
34. Pick. U., K. Gounaris, M. Weiss, and J. Barber. 1985. Tightly bound sulpholipids in chloroplast CF0-CF1. Biochim. Biophys. Acta. 808: 415-420.
35. Ram, P., E. Kim, D. S. Thomson, K. P. Howard, and J. H. Prestegard. 1992. Computer modeling of glycolipids at membrane surfaces. Biophys. J. 63:1530-1535.
36. 1H NMR spectra of proteins via double quantum filtration. Biochem. Biophys. Res. Commun. 117:479-485.
37. Sanders, C. R., B. J. Hare, K. P. Howard, and J. H. Prestegard. 1994. Magnetically oriented phospholipid micelles as a tool for the study of membrane-associated molecules. Prog. NMR Spectrosc. 26:421-444.
38. Sanders, C. R., and J. H. Prestegard. 1990. Magnetically orientable phospholipid bilayers containing small amounts of a bile salt analoque, CHAPSO. Biophys. J. 58:447-460.
39. Sanders, C. R., and J. H. Prestegard. 1991. Orientation and dynamics of β-dodecyl glucopyranoside in phospholipid bilayers by oriented sample NMR and order matrix analysis. J Am. Chem. Soc. 113:1987-1996.
40. Sanders, C. R., and J. H. Prestegard. 1992. Headgroup orientations of alkyl glycosides at a lipid bilayer interface. J. Am. Chem. Soc. 114: 7096-7107.
41. Sato, N., and N. Murata. 1988. Membrane lipids. Methods Enzymol. 167:251-259.
42. Scarsdale, J. N., P. Ram, and J. H. Prestegard. 1988. A molecular mechanics-NMR pseudoenergy approach to the solution conformation of glycolipids. J. Comp. Chem. 9:133-147.
43. Shaka, A., J. Keeler, and R. Freeman. 1983. Evaluation of a new broadband decoupling sequence: WALTZ-16. J. Magn. Res. 53:313-340.
44. Siebert, H., G. Reuter, R. Schauer, C. von der Lieth, and J. Dabrowski. 1992. Solution conformations of GM3 gangliosides containing different sialic acid residues as revealed by NOE-based distance mapping, molecular mechanics, and molecular dynamics calculations. Biochemistry. 31:6962-6971.
45. Skarjune, R., and E. Oldfield. 1982. Physical studies of cell surface and cell membrane structure. Deuterium NMR studies of N-palmitoylglucosylceramide (cerebroside) head group structure. Biochemistry. 21: 3154-3160.
46. Smith, S. O., I. Kustanovich, S. Bhamidipati, A. Salmon, and J. A. Hamilton. 1992. Interfacial conformation of dipalmitoylglycerol and dipalmitoylphosphatidylcholine in phospholipid bilayers. Biochemistry. 31:11660-11664.
47. Still, W. C. 1990. Macromodel V3.1. Department of Chemistry, Columbia University, New York.
48. Strenk, L. M., P. W. Westerman, and J. W. Doane. 1985. A model of orientational ordering in phosphatidylcholine bilayers based on conformational analysis of the glycerol backbone region. Biophys. J. 48: 765-773.
49. Tvaroska, I., M. Hricovini, and E. Petrakova. 1989. An attempt to derive a new Karplus-type equation of vicinal proton-carbon coupling constants for C-O-C- H segments of bonded atoms. Carbohydr. Res. 189: 359-362.
50. Van den Berg, L., S. Sadiq, S. Lederman, and N. Latov. 1992. The gp120 glycoprotein of HIV-1 binds to sulfatide and to the myelin associated glycoprotein. J. Neurosci. Res. 33:513-518.
51. 1H NMR spectroscopy. Magn. Reson. Chem. 30:S74-S86.
52. Vanderkooi, G. 1991. Multibilayer structure of dimyristoylphosphatidylcholine dihydrate as determined by energy minimization. Biochemistry. 30:10760-10768.
53. Weiner, S. J., P. A. Kollman, D. A. Case, U. C. Singh, C. Ohio, G. Alogona, S. Profeta, P. J. Weider. 1984. A new force field for molecular mechanical simulation of nucleic acids and proteins. J. Am Chem. Soc. 106:765.
54. Weiner, S. J., P. A. Kollman, D. T. Nguyen, and D. A. Case. 1986. An all atom force field for simulations of proteins and nucleic acids. J. Comp. Chem. 7:230-252.
55. Weislow, O., R. Kiser, D. Fine, J. Bader, B. Shoemaker, and M. Boyd. 1989. New soluble-formazan assay for HIV-1 cytopathic effects: application to high flux screening of synthetic and natural products for AIDS-antiviral activity. J. Natl. Cancer Inst. 81:577-586.
56. Winsborrow, B. G., J. Brisson, I. C. P. Smith, and H. C. Jarrell. 1992. Influence of the membrane surface on glycolipid conformation and dynamics. Biophys. J. 63:428-437.