Advertisement

Metabolism and Role of O-Acetylated Sialic Acids

  • Roland Schauer
  • Hiltrud Schmid
  • Jörg Pommerencke
  • Matthias Iwersen
  • Guido Kohla
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 491)

Abstract

In the still growing family of sialic acids with more than 40 different derivatives of neuraminic acid, the interest of the scientific community is increasingly directed towards the O-acetylated species. In the past two decades it evolved that O-acetylated sialic acids play fundamental roles in the development of organisms, in the regulation of the immune system, in cancer processes and many other biological and pathophysiological events.

Keywords

Sialic Acid Neuraminic Acid Mouse Hepatitis Virus Free Sialic Acid Acetylneuraminic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    S. Kelm and R. Schauer (1997) Sialic acids in molecular and cellular interactions. Int Rev Cytol, 175:137–240.PubMedCrossRefGoogle Scholar
  2. 2.
    R. Schauer, S. Kelm, G. Reuter, P. Roggentin and L. Shaw (1995) Biochemistry and role of sialic acids, in: Biology of the Sialic Acids (A. Rosenberg, ed.) pp 7–67, Plenum Press, New York.Google Scholar
  3. 3.
    R. Schauer and J.P. Kamerling (1997) Chemisty, biochemistry and biology of sialic acids, in: Glycoproteins 11 (J. Montreuil, J.F.G. Vliegenthart and H. Schachter, eds.) pp 243–402, Elsevier, Amsterdam.CrossRefGoogle Scholar
  4. 4.
    A. Varki (1992) Diversity in the sialic acids. Glycobiology, 2:25–40.PubMedCrossRefGoogle Scholar
  5. 5.
    C. Traving and R. Schauer (1998) Structure, function and metabolism of sialic acids. Cell Mol.Life Sci., 54:1330–1349.PubMedCrossRefGoogle Scholar
  6. 6.
    L. Shaw and R. Schauer (1988) The biosynthesis of N-glycoloylneuraminic acid occurs by hydroxylation of the CMP-glycoside of N-acetylneuraminic acid. Biol Chem Hoppe Seyler, 369:477486.Google Scholar
  7. 7.
    A. Varki and S. Diaz (1985) The transport and utilization of acetyl coenzyme A by rat liver Golgi vesicles. O-acetylated sialic acids are a major product. J Biol Chem, 260:6600–6608.PubMedGoogle Scholar
  8. 8.
    V. Vandamme-Feldhaus and R. Schauer (1998) Characterization of the enzymatic 7-O-acetylation of sialic acids and evidence for enzymatic O-acetyl migration from C-7 to C-9 in bovine submandibular gland. J Biochem (Tokyo), 124:111–121.CrossRefGoogle Scholar
  9. 9.
    R. Schauer, S. Stoll and G. Reuter (1991) Differences in the amount of N-acetyl-and N-glycoloylneuraminic acid, as well as O-acylated sialic acids, of fetal and adult bovine tissues. Carbohydr Res, 213:353–359.PubMedCrossRefGoogle Scholar
  10. 10.
    W.X. Shi, R. Chammas and A. Varki (1998) Induction of sialic acid 9-O-acetylation by diverse gene products: implications for the expression cloning of sialic acidO-acetyltransferases. Glycobiology, 8:199–205.PubMedCrossRefGoogle Scholar
  11. 11.
    G. Herder, R. Rott, H.D. Klenk, H.P. Müller, A.K. Shukla and R. Schauer (1985) The receptor-destroying enzyme of influenza C virus is neuraminate-O-acetylesterase. EMBO J, 4:1503–1506.Google Scholar
  12. 12.
    H. Takematsu, S. Diaz, A. Stoddart, Y. Zhang and A. Varki (1999) Lysosomal and cytosolic sialic acid 9-O-acetylesterase activities can be encoded by one gene via differential usage of a signal peptide-encoding exon at the N terminus. J Biol Chem, 274:25623–25631.CrossRefGoogle Scholar
  13. 13.
    G. Regl, A. Kaser, M. Iwersen, H. Schmid, G. Kohla, B. Strobl, U. Vilas, R. Schauer and R. Vlasak (1999) The hemagglutinin-esterase of mouse hepatitis virus strain S is a sialate-4-O-acetylesterase. J Virol, 73:4721–4727.PubMedGoogle Scholar
  14. 14.
    A.P. Corfield, M. Sander-Wewer, R.W. Veh, M. Wember and R. Schauer (1986) The action of sialidases on substrates containing 0-acetylsialic acids. Biol Chem Hoppe Seyler, 367:433–439.PubMedCrossRefGoogle Scholar
  15. 15.
    T.P. Mawhinney and D.L. Chance (1994) Hydrolysis of sialic acids and O-acetylated sialic acids with propionic acid. Anal Biochem, 223:164–167.PubMedCrossRefGoogle Scholar
  16. 16.
    G. Reuter and R. Schauer (1994) Determination of sialic acids. Methods Enzymol, 230:168–199.PubMedCrossRefGoogle Scholar
  17. 17.
    A.E. Manzi, S. Diaz and A. Varki (1990) High-pressure liquid chromatography of sialic acids on a pellicular resin. Anal Biochem, 188:20–32.PubMedCrossRefGoogle Scholar
  18. 18.
    S. Hara, M. Yamaguchi, Y. Takemori, K. Furuhata, H. Ogura and M. Nakamura (1989) Determination of mono-O-acetylated N-acetylneuraminic acids in human and rat sera by fluorometric high-performance liquid chromatography. Anal Biochem, 179:162–166.PubMedCrossRefGoogle Scholar
  19. 19.
    A. Klein, S. Diaz, I. Ferreira, G. Lamblin, P. Roussel and A.E. Manzi (1997) New sialic acids from biological sources identified by a comprehensive and sensitive approach: liquid chromatographyelectrospray ionization-mass spectrometry (LC-ESI-MS) of SIA quinoxalinones. Glycobiology, 7:421432.Google Scholar
  20. 20.
    J.P. Kamerling and J.F. Vliegenthart (1975) Identification of O-acetylated N-acylneuraminic acids by mass spectrometry. Carbohydr Res, 41:7–17.PubMedCrossRefGoogle Scholar
  21. 21.
    J.F. Vliegenthart, L. Dorland, H. van Halbeek and J. Haverkamp (1982) NMR Spectroscopy of sialic acids, in: Sialic Acids (R. Schauer, ed.) pp 127–172, Springer-Verlag, Wien.CrossRefGoogle Scholar
  22. 22.
    G. Harms, G. Reuter, A.P. Corfield and R. Schauer (1996) Binding specificity of influenza C virus to variably O-acetylated glycoconjugates and its use for histochemical detection of N-acetyl-9-Oacetylneuraminic acid in mammalian tissues. Glycoconj J, 13:621–630.PubMedCrossRefGoogle Scholar
  23. 23.
    G. Zimmer, G. Reuter and R. Schauer (1992) Use of influenza C virus for detection of 9-O-acetylated sialic acids on immobilized glycoconjugates by esterase activity. Eur J Biochem, 204:209–215.PubMedCrossRefGoogle Scholar
  24. 24.
    R. Schauer, G. Reuter, S. Stoll, d.R. Posadas, G. Herrler and H.D. Klenk (1988) Isolation and characterization of sialate 9(4)-O-acetylesterase from influenza C virus. Biol Chem Hoppe Seyler, 369:1121–1130.PubMedCrossRefGoogle Scholar
  25. 25.
    M.M. Iglesias, G.D. Cymes and C. Wolfenstein-Todel (1996) A sialic acid-binding lectin from ovine placenta: purification, specificity and interaction with actin. Glycoconj J, 13:967–976.PubMedCrossRefGoogle Scholar
  26. 26.
    C. Mandal and S. Basu (1987) An unique specificity of a sialic acid binding lectin AchatininH, from the hemolymph ofAchatina fulicasnail. Biochem Biophys Res Commun, 148:795–801.PubMedCrossRefGoogle Scholar
  27. 27.
    G.A. Fragkiadakis and E.K. Stratakis (1997) The lectin from the crustaceanLiocarcinus depuratorrecognizes O-acetyl sialic acids. Comp Biochem Physiol B Biochem Mol Biol, 117:545–552.PubMedCrossRefGoogle Scholar
  28. 28.
    M.H. Ravindranath and J.C. Paulson (1987) O-acetylsialic acid-specific lectin from the crabCancer anntenarius.Methods Enzymol, 138:520–527.PubMedCrossRefGoogle Scholar
  29. 29.
    E. Cerato, S. Birkle, J. Portoukalian, A. Mezazigh, J.F. Chatal and J. Aubry (1997) Variable region gene segments of nine monoclonal antibodies specific to disialogangliosides (GD2, GD3) and theirOacetylated derivatives. Hybridoma, 16:307–316.PubMedCrossRefGoogle Scholar
  30. 30.
    B. Kniep, C. Claus, J. Peterkatalinic, D.A. Monner, W. Dippold and M. Nimtz (1995) 7-O-acetyl-GD3 in human T-lymphocytes is detected by a specific T-cell-activating monoclonal antibody. J.Biol.Chem., 270:30173–30180.PubMedCrossRefGoogle Scholar
  31. 31.
    M. Koga, N. Yuki, T. Ariga and K. Hirata (1999) Antibodies to GD3, GT3, and O-acetylated species in Guillain-Barré and Fisher’s syndromes: their association with cranial nerve dysfunction. J Neurol Sci, 164:50–55.PubMedCrossRefGoogle Scholar
  32. 32.
    G. Zhang, L. Ji, S. Kurono, S.C. Fujita, S. Furuya and Y. Hirabayashi (1997) Developmentally regulated O-acetylated sialoglycans in the central nervous system revealed by a new monoclonal antibody 493D4 recognizing a wide range of O-acetylated glycoconjugates. Glycoconj J, 14:847–857.PubMedCrossRefGoogle Scholar
  33. 33.
    I. Miyoshi, H. Higashi, Y. Hirabayashi, S. Kato and M. Naiki (1986) Detection of 4-O-acetyl-Nglycolylneuraminyl lactosylceramide as one of tumor-associated antigens in human colon cancer tissues by specific antibody. Mol Immunol, 23:631–638.PubMedCrossRefGoogle Scholar
  34. 34.
    S. Inoue, M. Iwasaki, K. Ishii, K. Kitajima and Y. Inoue (1989) Isolation and structures of glycoproteinderived free sialooligosaccharides from the unfertilized eggs ofTribolodon hakonensisa dace. Intracellular accumulation of a novel class of biantennary disialooligosaccharides. J Biol Chem, 264:18520–18526.PubMedGoogle Scholar
  35. 35.
    G. Lochnit and R. Geyer (1995) Carbohydrate structure analysis of batroxobin, a thrombin-like serine protease fromBothrops moojenivenom. Eur J Biochem, 228:805–816.PubMedCrossRefGoogle Scholar
  36. 36.
    J.P. Kamerling, L. Dorland, H. van Halbeek, J.F. Vliegenthart, M. Messer and R. Schauer (1982) Structural studies of 4-O-acetyl-a-N-acetylneuraminyl-(2 goes to 3)-lactose, the main oligosaccharide in echidna milk. Carbohydr Res, 100:331–340.PubMedCrossRefGoogle Scholar
  37. 37.
    A. Klein and P. Roussel (1998) O-acetylation of sialic acids. Biochimie, 80:49–57.PubMedCrossRefGoogle Scholar
  38. 38.
    K. Hanaoka, T.J. Pritchett, S. Takasaki, N. Kochibe, S. Sabesan, J.C. Paulson and A. Kobata (1989) 4O-acetyl-N-acetylneuraminic acid in the N-linked carbohydrate structures of equine and guinea pig et,- macroglobulins, potent inhibitors of influenza virus infection. J Biol Chem, 264:9842–9849.PubMedGoogle Scholar
  39. 39.
    M. Iwersen, V. Vandamme-Feldhaus and R. Schauer (1998) Enzymatic 4-O-acetylation ofNacetylneuraminic acid in guinea-pig liver. Glycoconj J, 15:895–904.PubMedCrossRefGoogle Scholar
  40. 40.
    H.H. Higa, C. Butor, S. Diaz and A. Varki (1989) O-acetylation and de-O-acetylation of sialic acids.Oacetylation of sialic acids in the rat liver Golgi apparatus involves an acetyl intermediate and essential histidine and lysine residues--a transmembrane reaction? J Biol Chem, 264:19427–19434.PubMedGoogle Scholar
  41. 41.
    R. Schauer (1970) Biosynthesis of N-acetyl-O-acetylneuraminic acids. I. Incorporation of [14C] acetate into sections of the submaxillary salivary gland of ox and horse. Hoppe Seylers Z Physiol Chem, 351:595–602.PubMedCrossRefGoogle Scholar
  42. 42.
    R. Schauer (1978) Characterization of sialic acids. Methods Enzymol, 50:64–89.PubMedCrossRefGoogle Scholar
  43. 43.
    S. Gasa, A. Makita and Y. Kinoshita (1983) Further study of the chemical structure of the equine erythrocyte hematoside containing O-acetyl ester. J Biol Chem, 258:876–881.PubMedGoogle Scholar
  44. 44.
    V. Pozsgay, H. Jennings and D.L. Kasper (1987) 4,8-anhydro-N-acetylneuraminic acid. Isolation from edible birds nest and structure determination. Eur J Biochem, 162:445–450.PubMedCrossRefGoogle Scholar
  45. 45.
    A.E. Manzi, A. Dell, P. Azadi and A. Varki (1990) Studies of naturally occurring modifications of sialic acids by fast-atom bombardment-mass spectrometry. Analysis of positional isomers by periodate cleavage. J Biol Chem, 265:8094–8107.PubMedGoogle Scholar
  46. 46.
    M.N. Matrosovich, A.S. Gambaryan and M.P. Chumakov (1992) Influenza viruses differ in recognition of 4–0-acetyl substitution of sialic acid receptor determinant. Virology, 188:854–858.PubMedCrossRefGoogle Scholar
  47. 47.
    T.J. Pritchett and J.C. Paulson (1989) Basis for the potent inhibition of influenza virus infection by equine and guinea pig a2macroglobulin. J Biol Chem, 264:9850–9858.PubMedGoogle Scholar
  48. 48.
    G. Menghi, L. Marchetti, A.M. Bondi and G. Materazzi (1996) Sialylation patterns of the mouse parotid secretory granules. Combined deacetylation, enzymatic degradation and lectin-gold binding. Eur J Morphol, 34:181–185.PubMedGoogle Scholar
  49. 49.
    A. Varki and S. Kornfeld (1980) An autosomal dominant gene regulates the extent of9-O-acetylation of murine erythrocyte sialic acids. A probable explanation for the variation in capacity to activate the human alternate complement pathway. J Exp Med, 152:532–544.PubMedCrossRefGoogle Scholar
  50. 50.
    A. Varki, F. Hooshmand, S. Diaz, N.M. Varki and S.M. Hedrick (1991) Developmental abnormalities in transgenic mice expressing a sialic acid-specific 9-O-acetylesterase. Cell, 65:65–74.PubMedCrossRefGoogle Scholar
  51. 51.
    M.L. Rodrigues, S. Rozental, J.N.S.S. Couceiro, J. Angluster, C.S. Alviano and L.R. Travassos (1997) Identification of N-acetylneuraminic acid and its 9-O-acetylated derivative on the cell surface ofCryptococcus neoformans:Influence on fungal phagocytosis. Infection and Immunity, 65:4937–4942.PubMedGoogle Scholar
  52. 52.
    A.P. Corfield, N. Myerscough, B.F. Warren, P. Durdey, C. Paraskeva and R. Schauer (1999) Reduction of sialic acid O-acetylation in human colonic mucins in the adenoma-carcinoma sequence. Glycoconjugate J., 16:307–317.CrossRefGoogle Scholar
  53. 53.
    U. Hubl, C. Fahr, E. Proksch and R. Schauer (1997) Nachweis O-acetylierter Ganglioside mit Influenza Viren in Melanomen and Basaliomen. Z.Hautkrankheiten, 72:258–264.Google Scholar
  54. 54.
    G. Herrler, G. Reuter, R. Rott, H.D. Klenk and R. Schauer (1987) N-acetyl-9-O-acetylneuraminic acid, the receptor determinant for influenza C virus, is a differentiation marker on chicken erythrocytes. Biol Chem Hoppe Seyler, 368:451–454.PubMedCrossRefGoogle Scholar
  55. 55.
    J.P. Kamerling, J. Makovitzky, R. Schauer, J.F. Vliegenthart and M. Wember (1982) The nature of sialic acids in human lymphocytes. Biochim Biophys Acta, 714:351–355.PubMedCrossRefGoogle Scholar
  56. 56.
    B. Kniep, W.A. Flegel, H. Northoff and E.P. Rieber (1993) CDw60 glycolipid antigens of human leukocytes: structural characterization and cellular distribution. Blood, 82:1776–1786.PubMedGoogle Scholar
  57. 57.
    M. Vater, B. Kniep, H.J. Gross, C. Claus, W. Dippold and R. Schwartz-Albiez (1997) The 9–0acetylated disialosyl carbohydrate sequence of CDw60 is a marker on activated human B lymphocytes. Immunol Lett, 59:151–157.PubMedCrossRefGoogle Scholar
  58. 58.
    C. Butor, S. Diaz and A. Varki (1993) High level O-acetylation of sialic acids on N-linked oligosaccharides of rat liver membranes. Differential subcellular distribution of 7- and 9-O-acetyl groups and of enzymes involved in their regulation. J Biol Chem, 268:10197–10206.PubMedGoogle Scholar
  59. 59.
    G. Reuter, S. Stoll, J.P. Kamerling, J.F. Vliegenthart and R. Schauer (1988) Sialic acids on erythrocytes and in blood plasma of mammals, in: Sialic Acids 1988 - Proceedings of the Japanese-German Symposium on Sialic Acids (R. Schauer and T. Yamakawa, eds.) pp 88–89, Verlag Wissenschaft and Bildung, Kiel.Google Scholar
  60. 60.
    R. Schauer (1970) Biosynthesis of N-acetyl-O-acetylneuraminic acids. II. Substrate and intracellular localization of bovine acetyl-coenzyme A: N-acetylneuraminate-7- and 8-O-acetyltransferase. Hoppe Seylers Z Physiol Chem, 351:749–758.PubMedCrossRefGoogle Scholar
  61. 61.
    R. Schauer (1987) Sialic acids: metabolism of O-acetyl groups. Methods Enzymol, 138:611–626.PubMedCrossRefGoogle Scholar
  62. 62.
    S. Diaz, H.H. Higa, B.K. Hayes and A. Varki (1989) O-acetylation and de-O-acetylation of sialic acids. 7- and 9-O-acetylation of a2,6-linked sialic acids on endogenous N-linked glycans in rat liver Golgi vesicles. J Biol Chem, 264:19416–19426.PubMedGoogle Scholar
  63. 63.
    J.P. Kamerling, R. Schauer, A.K. Shukla, S. Stoll, H. van Halbeek and J.F. Vliegenthart (1987) Migration of O-acetyl groups in N,O-acetylneuraminic acids. Eur J Biochem, 162:601–607.PubMedCrossRefGoogle Scholar
  64. 64.
    A.P. Corfield (1992) Bacterial sialidases - roles in pathogenicity and nutrition. Glycobiology, 2:509–521.PubMedCrossRefGoogle Scholar
  65. 65.
    R. Schauer, G. Reuter and S. Stoll (1988) Sialate O-acetylesterases: key enzymes in sialic acid catabolism. Biochimie, 70:1511–1519.PubMedCrossRefGoogle Scholar
  66. 66.
    R. Schauer, G. Reuter, S. Stoll and A.K. Shukla (1989) Partial purification and characterization of sialate O-acetylesterase from bovine brain. J Biochem (Tokyo), 106:143–150.Google Scholar
  67. 67.
    H.H. Higa, A. Manzi and A. Varki (1989) O-acetylation and de-O-acetylation of sialic acids. Purification, characterization, and properties of a glycosylated rat liver esterase specific for 9-O-acetylated sialic acids. J Biol Chem, 264:19435–19442.PubMedGoogle Scholar
  68. 68.
    H.C. Siebert, C.W. Vonderlieth, X. Dong, G. Reuter, R. Schauer, H.J. Gabius and J.F.G. Vliegenthart (1996) Molecular dynamics-derived conformation and intramolecular interaction analysis of theNacetyl-9-O-acetylneuraminicacid-containing ganglioside GDIa and NMR-based analysis of its binding to a human polyclonal immunoglobulin G fraction with selectivity for O-acetylated sialic acids. Glycobiology., 6:561–572.PubMedCrossRefGoogle Scholar
  69. 69.
    W.X. Shi, R. Chammas and A. Varki (1996) Regulation of sialic acid 9-O-acetylation during the growth and differentiation of murine erythroleukemia cells. J Biol Chem, 271:31517–31525.PubMedCrossRefGoogle Scholar
  70. 70.
    S. Kelm, R. Schauer, J.C. Manuguerra, H.J. Gross and P.R. Crocker (1994) Modifications of cell surface sialic acids modulate cell adhesion mediated by sialoadhesin and CD22. Glycoconj J, 11:576–585.PubMedCrossRefGoogle Scholar
  71. 71.
    K. Strenge, R. Schauer and S. Kelm (1999) Binding partners for the myelin-associated glycoprotein of N(2)A neuroblastoma cells. FEBS Lett., 444:59–64.PubMedCrossRefGoogle Scholar
  72. 72.
    H.H. Higa, G.N. Rogers and J.C. Paulson (1985) Influenza virus hemagglutinins differentiate between receptor determinants bearing N-acetyl-, N-glycolyl-, and N,O-diacetylneuraminic acids. Virology, 144:279–282.PubMedCrossRefGoogle Scholar
  73. 73.
    A. Gocht, G. Rutter and B. Kniep (1998) Changed expression of 9–0-acetyl GD3 (CDw60) in benign and atypical proliferative lesions and carcinomas of the human breast. Histochem Cell Biol, 110:217–229.PubMedCrossRefGoogle Scholar
  74. 74.
    G. Marquina, H. Waki, L.E. Fernandez, K. Kon, A. Carr, O. Valiente, R. Perez and S. Ando (1996) Gangliosides expressed in human breast cancer. Cancer Res., 56:5165–5171.PubMedGoogle Scholar
  75. 75.
    D.A. Cheresh, R.A. Reisfeld and A.P. Varki (1984) O-acetylation of disialoganglioside GD3 by human melanoma cells creates a unique antigenic determinant. Science, 225:844–846.PubMedCrossRefGoogle Scholar
  76. 76.
    S. Birklé, S. Ren, A. Slominski, G. Zeng, L. Gao and R.K. Yu (1999) Down-regulation of the expression of O-acetyl-GD3 by the O-acetylesterase cDNA in hamster melanoma cells: effects on cellular proliferation, differentiation, and melanogenesis. J Neurochem, 72:954–961.PubMedCrossRefGoogle Scholar
  77. 77.
    H. Araujo, M. Menezes and R. Mendez-Otero (1997) Blockage of 9-O-acetyl gangliosides induces microtubule depolymerization in growth cones and neurites. Eur J Cell Biol, 72:202–213.PubMedGoogle Scholar
  78. 78.
    L.E.A.M. Mello and R. Mendezotero (1996) Expression of 9-O-acetylated gangliosides in the rat hippocampus. Neurosci.Lett., 213:17–20.PubMedCrossRefGoogle Scholar
  79. 79.
    G. Reuter, R. Schauer and P. Bumm (1988) Sialic acids of human nasal mucin, possible targets of the influenza C viruses, in:Sialic Acids (R. Schauer and T. Yamakawa, eds.) pp 258–259, Berlin.Google Scholar
  80. 80.
    T. Ito, J.N. Couceiro, S. Kelm, L.G. Baum, S. Krauss, M.R. Castrucci, I. Donatelli, H. Kida, J.C. Paulson, R.G. Webster and Y. Kawaoka (1998) Molecular basis for the generation in pigs of influenza A viruses with pandemic potential. J Virol, 72:7367–7373.PubMedGoogle Scholar
  81. 81.
    T. Ariga, G.M. Blaine, H. Yoshino, G. Dawson, T. Kanda, G.C. Zeng, T. Kasama, Y. Kushi and R.K. Yu (1995) Glycosphingolipid composition of murine neuroblastoma cells: O-acetylesterase gene downregulates the expression of O-acetylated GD3. Biochemistry, 34:11500–11507.PubMedCrossRefGoogle Scholar
  82. 82.
    R. Schauer (1982) Chemistry, metabolism, and biological functions of sialic acids. Adv Carbohydr Chem Biochem, 40:131–234.PubMedCrossRefGoogle Scholar
  83. 83.
    A.P. Corfield and R. Schauer (1992) Metabolism of sialic acids, in: Sialic Acids - Chemistry, Metabolism and Function (R. Schauer, ed.) pp 195–261, Springer, Wien.Google Scholar
  84. 84.
    K. Kiehne and R. Schauer (1992) The influence of a-and ß-galactose residues and sialic acid O-acetyl groups of rat erythrocytes on the interaction with peritoneal macrophages. Biol Chem Hoppe Seyler, 373:1117–1123.PubMedCrossRefGoogle Scholar
  85. 85.
    R. Schauer (1991) Biosynthesis and function ofN-and O-substituted sialic acids. Glycobiology, 1:449452.Google Scholar
  86. 86.
    W.X. Shi, R. Chammas, N.M. Varki, L. Powell and A. Varki (1996) Sialic acid 9-O-acetylation on murine erythroleukemia cells affects complement activation, binding to l-type lectins, and tissue homing. J Biol Chem, 271:31526–31532.PubMedCrossRefGoogle Scholar
  87. 87.
    V. Koistinen (1992) Limited tryptic cleavage of complement factor H abrogates recognition of sialic acid-containing surfaces by the alternative pathway of complement. Biochem J, 283 (Pt 2):317–319.PubMedGoogle Scholar
  88. 88.
    F.W. Klotz, P.A. Orlandi, G. Reuter, S.J. Cohen, J.D. Haynes, R. Schauer, R.J. Howard, P. Palese and L.H. Miller (1992) Binding of Plasmodium falciparum 175-kilodalton erythrocyte binding antigen and invasion of murine erythrocytes requires N-acetylneuraminic acid but not its O-acetylated form. Mol Biochem Parasitol, 51:49–54.PubMedCrossRefGoogle Scholar
  89. 89.
    A.F. Pacitti and J.R. Gentsch (1987) Inhibition of reovirus type 3 binding to host cells by sialylated glycoproteins is mediated through the viral attachment protein. J Virol, 61:1407–1415.PubMedGoogle Scholar
  90. 90.
    A. Shugaba, I. Umar, J. Omage, N.D. Ibrahim, J. Andrews, A.I. Ukoha, D.I. Saror and K.A. Esievo (1994) Biochemical differences (O-acetyl and glycolyl groups) in erythrocyte surface sialic acids of trypanotolerant N’dama and trypanosusceptible Zebu cattle. J Comp Pathol, 110:91–95.PubMedCrossRefGoogle Scholar
  91. 91.
    B. Schultze, H.J. Gross, R. Brossmer, H.D. Klenk and G. Herrler (1990) Hemagglutinating encephalomyelitis virus attaches to N-acetyl-9-O-acetylneuraminic acid-containing receptors on erythrocytes: comparison with bovine coronavirus and influenza C virus. Virus Res, 16:185–194.PubMedCrossRefGoogle Scholar
  92. 92.
    B. Schultze, H.J. Gross, R. Brossmer and G. Herrler (1991) The S protein of bovine coronavirus is a hemagglutinin recognizing 9-O-acetylated sialic acid as a receptor determinant. J Virol, 65:6232–6237.PubMedGoogle Scholar
  93. 93.
    M. Larkin, W. Knapp, M.S. Stoll, H. Mehmet and T. Feizi (1991) Monoclonal antibodies VIB-E3, 1B5 and HB9 to the leucocyte/epithelial antigen CD24 resemble BA-1 in recognizing sialic acid-dependent epitope(s). Evidence that VIB-E3 recognizes NeuAc a2–6GaINAc and NeuAc a2–6Gal sequences. Clin Exp lmmunol, 85:536–541.Google Scholar
  94. 94.
    R. Schauer (1988) Sialic acids as antigenic determinants of complex carbohydrates. Adv Exp Med Biol, 228:47–72.PubMedCrossRefGoogle Scholar
  95. 95.
    H. Frasa, J. Procee, R. Torensma, A. Verbruggen, A. Algra, M. Rozenberg-Arska, K. Kraaijeveld and J. Verhoef (1993)Escherichia coliin bacteremia: 0-acetylated K1 strains appear to be more virulent than non-O-acetylated K1 strains. J Clin Microbiol, 31:3174–3178.PubMedGoogle Scholar
  96. 96.
    G. Sen and C. Mandai (1995) The specificity of the binding site of AchatininH, a sialic acid-binding lectin fromAchatina fulica.Carbohydr Res, 268:115–125.PubMedCrossRefGoogle Scholar
  97. 97.
    F.Y. Zeng and H.J. Gabius (1992) Sialic acid-binding proteins: characterization, biological function and application. Z Naturforsch.(C.), 47:641–653.Google Scholar
  98. 98.
    S. Agawa and J.R. Jass (1990) Sialic acid histochemistry and the adenoma-carcinoma sequence in colorectum. J Clin Pathol, 43:527–532.PubMedCrossRefGoogle Scholar
  99. 99.
    A.S. Blum and C.J. Barnstable (1987) O-acetylation of a cell-surface carbohydrate creates discrete molecular patterns during neural development. Proc Natl Acad Sci U S A, 84:8716–8720.PubMedCrossRefGoogle Scholar
  100. 100.
    C.B. Huang, J.A. Xu, K.R. Wu and W.M. Wang (1988) O-acetyl sialomucin and differentiation of stomach cancer: a histochemical study. Anticancer Res, 8:829–832.PubMedGoogle Scholar
  101. 101.
    J.T. Hutchins and C.L. Reading (1988) Characterization of mono-, di-, and tri-O-acetylated sialic acids on human cells. J Cell Biochem, 37:37–48.PubMedCrossRefGoogle Scholar
  102. 102.
    J.R. Jass and A.M. Roberton (1994) Colorectal mucin histochemistry in health and disease: a critical review. Pathol Int, 44:487–504.PubMedCrossRefGoogle Scholar
  103. 103.
    A.S. Palier, S.L. Arnsmeier, J.K. Robinson and E.G. Bremer (1992) Alteration in keratinocyte ganglioside content in basal cell carcinomas. J Invest Dermatol, 98:226–232.CrossRefGoogle Scholar
  104. 104.
    J. Reivinen, H. Holthofer and A. Miettinen (1994) O-acetyl GD3 ganglioside in human peripheral blood T lymphocytes. lnt Immunol, 6:1409–1416.Google Scholar
  105. 105.
    G. Sen, M. Chowdhury and C. Mandal (1994) 0-acetylated sialic acid as a distinct marker for differentiation between several leukemia erythrocytes. Mol Cell Biochem, 136:65–70.PubMedCrossRefGoogle Scholar
  106. 106.
    M. Heidenheim, E.R. Hansen and O. Baadsgaard (1995) CDw60, which identifies the acetylated form of GD3 gangliosides, is strongly expressed in human basal cell carcinoma. Br J Dermatol, 133:392–397.PubMedCrossRefGoogle Scholar
  107. 107.
    B. Mann, E. Klussmann, V. Vandammefeldhaus, M. Iwersen, M.L. Hanski, E.O. Riecken, H.J. Buhr, R. Schauer, Y.S. Kim and C. Hanski (1997) Low O-acetylation of sialyl-Le(x) contributes to its overexpression in colon carcinoma metastases. Int.J.Cancer, 72:258–264.PubMedCrossRefGoogle Scholar
  108. 108.
    D.S. Gupta, B. Jann and K. Jann (1984)Escherichia coltOl8ac antigen: structure of the O-specific polysaccharide moiety. Infect Immun, 45:203–209.PubMedGoogle Scholar
  109. 109.
    C.G. Hellerqvist, B. Lindberg, S. Svensson, T. Holme and A.A. Lindberg (1969) Structural studies on the O-specific side chains of the cell wall lipopolysaccharides fromSalmonella typhiandS. enteritidis.Acta Chem Scand, 23:1588–1596.PubMedCrossRefGoogle Scholar
  110. 110.
    B.A. Dmitriev, Y.A. Knirel, N.K. Kochetkov, B. Jann and K. Jann (1977) Cell-wall lipopolysaccharide of the ‘Shigella-like’Escherichia coli058. Structure of the polysaccharide chain. Eur J Biochem, 79:111–115.PubMedCrossRefGoogle Scholar
  111. 111.
    B.A. Dmitriev, L.V. Backinowsky, Y.A. Knirel, N.K. Kochetkov and I.L. Hofmann (1977) Somatic antigens of Shigella. The strucuture of the specific polysaccharide chain ofShigella dysenteriaetype 5 lipopolysaccharide. Eur J Biochem, 78:381–387.PubMedCrossRefGoogle Scholar
  112. 112.
    B. Lindberg, J. Lönngren and W. Nimmich (1972) Structural studies of the Klebsiella O group 9 lipopolysaccharide. Carbohydr Res, 23:47–55.PubMedCrossRefGoogle Scholar
  113. 113.
    N.P. Arbatsky, A.S. Shashkov, G. Widmalm, Y.A. Knirel, K. Zych and Z. Sidorczyk (1997) Structure of the 0-specific polysaccharide ofProteus penneristrain 25 containing N-(L-alanyl) and multipleO-acetyl groups in a tetrasaccharide repeating unit. Carbohydr Res, 298:229–235.PubMedCrossRefGoogle Scholar
  114. 114.
    E.V. Vinogradov, R. Pantophlet, S.R. Haseley, L. Brade, O. Holst and H. Brade (1997) Structural and serological characterisation of the O-specific polysaccharide from lipopolysaccharide ofAcinetobacter calcoaceticusstrain 7 (DNA group 1). Eur J Biochem, 243:167–173.PubMedCrossRefGoogle Scholar
  115. 115.
    S.N. Senchenkova, A.S. Shashkov, Y.A. Knirel, J.J. McGovern and A.P. Moran (1997) The O-specific polysaccharide chain ofCampylobacter fetusserotype A lipopolysaccharide is a partially O-acetylated 1,3-linked a-D-manean. Eur J Biochem, 245:637–641.PubMedCrossRefGoogle Scholar
  116. 116.
    A.I. Fattom, J. Sarwar, L. Basham, S. Ennifar and R. Naso (1998) Antigenic determinants ofStaphylococcus aureustype 5 and type 8 capsular polysaccharide vaccines. Infect Immun, 66:4588–4592.PubMedGoogle Scholar
  117. 117.
    X. Lemercinier and C. Jones (1996) Full ‘H NMR assignment and detailed O-acetylation patterns of capsular polysaccharides fromNeisseria meningitidisused in vaccine production. Carbohydr Res, 296:83–96.PubMedCrossRefGoogle Scholar
  118. 118.
    G. Kogan, B. Jann and K. Jann (1992) Structure of theEscherichia coli0104 polysaccharide and its identity with the capsular K9 polysaccharide. FEMS Microbiol Lett, 70:135–140.PubMedCrossRefGoogle Scholar
  119. 119.
    A. Gamian, E. Romanowska, J. Ulrich and J. Defaye (1992) The structure of the sialic acid-containingEscherichia coli0104 O-specific polysaccharide and its linkage to the core region in lipopolysaccharide. Carbohydr Res, 236:195–208.PubMedCrossRefGoogle Scholar
  120. 120.
    C.A. Clark, J. Beltrame and P.A. Manning (1991) Theoacgene encoding a lipopolysaccharide O-antigen acetylase maps adjacent to the integrase-encoding gene on the genome ofShigellafexneribacteriophage Sf6. Gene, 107:43–52.PubMedCrossRefGoogle Scholar
  121. 121.
    J.M. Slauch, A.A. Lee, M.J. Mahan and J.J. Mekalanos (1996) Molecular characterization of theoafAlocus responsible for acetylation ofSalmonella typhimuriumO-antigen: oafA is a member of a family of integral membrane trans-acylases. J Bacteriol, 178:5904–5909.PubMedGoogle Scholar
  122. 122.
    C.H. Zou, Y.A. Knirel, J.H. Helbig, U. Zähringer and C.S. Mintz (1999) Molecular cloning and characterization of a locus responsible for O-acetylation of the O-polysaccharide ofLegionella pneumophilaserogroup 1 lipopolysaccharide. J Bacteriol, 181:4137–4141.PubMedGoogle Scholar
  123. 123.
    G. Stevenson, B. Neal, D. Liu, M. Hobbs, N.H. Packer, M. Batley, J.W. Redmond, L. Lindquist and P. Reeves (1994) Structure of the O-antigen ofEscherichia coltK-12 and the sequence of itsribgene cluster. J Bacteriol, 176:4144–4156.PubMedGoogle Scholar
  124. 124.
    S. Bystricky and S.C. Szu (1994) O-acetylation affects the binding properties of the carboxyl groups on the Vi bacterial polysaccharide. Biophys Chem, 51:1–7.PubMedCrossRefGoogle Scholar
  125. 125.
    G. Arakere and C.E. Frasch (1991) Specificity of antibodies to O-acetyl-positive and O-acetyl-negative group C meningococcal polysaccharides in sera from vaccinees and carriers. Infect Immun, 59:4349–4356.PubMedGoogle Scholar
  126. 126.
    F. Orskov, I. Orskov, A. Sutton, R. Schneerson, W. Lin, W. Egan, G.E. Hoff and J.B. Robbins (1979) Form variation inEscherichia coltK1: determined by O-acetylation of the capsular polysaccharide. J Exp Med, 149:669–685.PubMedCrossRefGoogle Scholar
  127. 127.
    W.X. Shi, R. Chammas and A. Varki (1996) Linkage-specific action of endogenous sialic acidOacetyltransferase in Chinese hamster ovary cells. J.Biol.Chem., 271:15130–15138.PubMedCrossRefGoogle Scholar
  128. 128.
    A. Kanamori, J. Nakayama, M.N. Fukuda, W.B. Stallcup, K. Sasaki, M. Fukuda and Y. Hirabayashi (1997) Expression cloning and characterization of a cDNA encoding a novel membrane protein required for the formation of O-acetylated ganglioside: A putative acetyl-CoA transporter. Proc.NatI.Acad.Sci.USA, 94:2897–2902.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2001

Authors and Affiliations

  • Roland Schauer
    • 1
  • Hiltrud Schmid
    • 1
  • Jörg Pommerencke
    • 1
  • Matthias Iwersen
    • 1
  • Guido Kohla
    • 1
  1. 1.Christian-Albrechts-Universität Olshausenstraße 40Biochemisches InstitutKielGermany

Personalised recommendations