Abstract
Detailed knowledge of the three-dimensional structure of ganglioside headgroups has allowed the successful design of structural and functional mimics of ganglioside GM1 oligosaccharide. Our recent work in this area is reviewed in this paper.
Similar content being viewed by others
REFERENCES
Karlsson, K.-A. 1989. Animal glycosphingolipids as membrane attachment sites for bacteria. Annu. Rev. Biochem. 58:309-350.
Hakomori, S.-I. 1990. Bifunctional role of glycosphingolipids. J. Biol. Chem. 265:18713-18716.
Nagai, Y. 1998. Ganglioside reasearch: new trends and reflections. Pure Appl. Chem. 70:533-538.
For leading references, see Rao, V. S. R., Qasba, P. K., Baloyi, P. V., and Chandrasekaran, R. 1998. Conformation of carbohydrates, Harwood Academic Publishers.
Poppe, L., Dabrowski, J., von der Lieth, C. W., Numata, M., and Ogawa, T. 1989. Solution conformation of sialosylcerebroside (GM4) and its NeuAc(α2-3)Galβ sugar component. Eur. J. Biochem. 180:337-342.
Siebert, H.-C., Reuter, G., Schauer, R., von der Lieth, C. W., and Dabrowski, J. 1992. Solution conformation 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.
Sabesan, S., Block, K., and Lemieux, R. U. 1984. The conformational properties of the gangliosides GM2 and GM1 based on 1H and 13C nuclear magnetic resonance. Can. J. Chem. 62:1034-1045.
Li, Y.-T., Li, S.-C., Hasegawa, A., Ishida, H., Kiso, M., Bernardi, A., Brocca, P., Raimondi, L., and Sonnino, S. 1999. Structural basis for the resistance of Tay-Sachs ganglioside GM2 to enzymatic degradation. J. Biol. Chem. 274:10014-10018.
Acquotti, D., Poppe, L., Dabrowski, J., von der Lieth, C. W., Sonnino, S., and Tettamanti, G. 1990. Three-dimensional structure of the oligosaccharide chain of ganglioside revealed by distance mapping procedure: a rotating and laboratory frame nuclear Overhauser enhancement investigation of native glycolipid in dimethyl sulfoxide and in water-dodecylphosphocoline solution. J. Am. Chem. Soc. 112:7772-7778.
Brocca, P., Berthault, P., and Sonnino, S. 1998. Conformation of the oligosaccharide chain of GM1 ganglioside in a carbohydrate-enriched surface. Biophys. J. 74:309-318.
Poppe, L., van Halbeek, H., Acquotti, D., and Sonnino, S. 1994. Carbohydrate dynamics at a micellar surface: GD1a headgroup transformations revealed by NMR spectroscopy. Biophys. J. 66:1642-1652.
Aubin, Y., Ito, Y., Paulson, J. C., and Prestegard, J. H. 1993. Structure and dynamics of the sialic acid moiety of GM3-ganglioside at the surface of a magnetically oriented membrane. Biochemistry 32:13405-13413.
Barber, K. R., Hamilton, K. S., Rigby, A. C., and Grant, C. W. M. 1994. Behaviour of complex oligosaccharides at a bilayer membrane surface probed by 2H-NMR. Biochem. Biophys. Acta 1190:376-384.
Singh, D. M., Shan, X., Davis, J. H., Jones, D. H., and Grant, C. W. M. 1995. Oligosaccharide behavior of compless natural glycosphingolipids in multicomponent model membrane. Biochemistry 34:451-463.
Jones, D. H., Barber, K. R., and Grant, C. W. M. 1996. Minor influence of sialic acid on conformation of a membrane-bound oligosaccharide recognition site. Biochemistry 35:4803-4811.
Breg, J., Kroon-Batenburg, L. M. J., Strecker, G., Montreuil, J., and Vliegenthart, J. F. G. 1989. Conformational analysis of the sialylα(2-3)N-acetyllactosamine structural element occurring in glycoproteins, by two-dimensional NOE 1H-NMR spectroscopy in combination with energy calculations by hard-sphere exoanomeric and molecular mechanics force fields with H-bonding potentials. Eur. J. Biochem. 178:727-739.
Sabesan, S., Bock, K., and Paulson, J. C. 1991. Conformational analysis of sialyloligosaccharides. Carb. Res. 218:27-54.
Scardsale, J. N., Prestegard, J. H., and Yu, R. K. 1990. NMR and computational studies of interaction between remote residues in gangliosides. Biochemistry 20:9843-9855.
Bernardi, A. and Raimondi, L. 1995. Conformational analysis of GM1 oligosaccharides in water solution with a new set of parameters for the Neu5Ac moiety. J. Org. Chem. 60:3370-3377.
Mukhopadhyay, C. and Bush, C. A. 1994. Molecular dynamics simulations of oligosaccharides containing N-acetylneuraminic acid. Biopolymers 34:11-20.
Brocca, P., Bernardi, A., Raimondi, L., and Sonnino, S. 2000. Modeling ganglioside headgroups by conformational analysis and molecular dynamics Glycoconj. J. 17:283-299.
Schulte, J., Lauterwein, J., and Hoeweler, U. 2000. NMR analysis of the configuration and conformation of N-acetylneuraminosyl-(2→3)-lactose. Magn. Reson. Chem. 38:751-756.
Spangler, B. D. 1992. Structure and function of cholera toxin and the related Escherichia coli heat-labile enterotoxin Microbiol. Rev. 56:622-647.
Merrit, E. A., Sarfaty, S., v. d. Akker, F., L'Hoir, C., Martial, J. A., and Hol, W. G. J. 1994. Crystal structure of cholera toxin B-pentamer bound to receptor GM1 pentasaccaride Prot. Sci. 3:166-175.
Merrit, E. A., Sarfaty, S., Jobling, M. G., Chang, T., Holmes, R. K., Hirst, T. R., and Hol, W. G. J. 1997. Structural studies of receptor binding by cholera toxin mutants Prot. Sci. 6:1516-1528.
Merrit, E. A. and Hol, W. G. J. 1995. AB5 toxins Curr. Opin. Struct. Biol. 5:165-171, and references therein.
Bernardi, A., Brocca, P., Checchia, A., Sonnino, S., and Zuccotto, F. 1999. Sugar mimics: an artificial receptor for cholera toxin. J. Am. Chem. Soc. 121:2032-2036.
Bernardi, A., Arosio, D., Manzoni, L., Micheli, F., Pasquarello, S., and Seneci, P. 2001. Stereoselective synthesis of conformationally constrained cyclohexanediols: a set of molecular scaffolds for the synthesis of glycomimetics. J. Org. Chem. 66:6209-6216.
Bax, A. and Davis, D. G. 1985. Separation of chemical exchange and cross-relaxation effects in two-dimensional NMR spectroscopy J. Magn. Res. 64:533-535.
Bernardi, A., Carrettoni, L., Grosso Ciponte, A., Monti, D., and Sonnino, S. 2000. Second generation mimics of ganglioside GM1 as artificial receptor for cholera toxin: replacement of sialic acid moiety. Bioorg. Med. Chem. Lett. 2197-2301.
Schön, A. and Freire, E. 1989. Thermodynamics of intersubunit interaction in cholera toxin upon binding to the oligosaccharide portion of its cell surface receptor, ganglioside GM1. Biochemistry. 28:5019-5024.
Calculation were performed using MacroModel (Mohamadi, F., Richards, N. G. J., Guida, W. G., Liskamp, R., Lipton, M., Caufield, C., Chang, G., Hendrickdon, T., and Still, W. C. 1990. MacroModel-an integrated software system for modeling organic and bioorganic molecules using molecular mechanics J. Comput. Chem. 11:440-467) and following the protocol described in Refs. 27 and 33.
Bernardi, A., Raimondi, L., and Zuccotto, F. 1997. Simulation of protein-sugar interactions: a computational model of the complex between ganglioside GM1 and the heat-labile enterotoxin of Escherichia coli J. Med. Chem. 40:1855-1865.
Mertz, J. A., McCann, J. A., and Picking, W. D. 1996. Fluorescence analysis of galactose, lactose, and fucose interaction with cholera toxin B subunit Biochem. Biophys. Res. Commun. 226:140-144.
Schengrund, C. L. and Ringler, N. J. 1989. Binding of Vibrio cholera toxin and the heat-labile enterotoxin of Escherichia coli to GM1, derivatives of GM1, and nonlipid oligosaccharide polyvalent ligands J. Biol. Chem. 264:13233-13237.
Bernardi, A., Potenza, D., Capelli, A. M., Garcia-Herrero, A., Canada, F. J., and Jimenez-Barbero, J. Second generation mimics of ganglioside GM1. A three-dimensional view of their interactions with bacterial enterotoxins by NMR and computational methods. Chem. Eur. J. 2002, in press.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bernardi, A., Arosio, D. & Sonnino, S. Mimicking Gangliosides by Design: Mimics of GM1 Headgroup. Neurochem Res 27, 539–545 (2002). https://doi.org/10.1023/A:1020251428217
Issue Date:
DOI: https://doi.org/10.1023/A:1020251428217