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Specificity of the binding site of the sialic acid-binding lectin from ovine placenta, deduced from interactions with synthetic analogues

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Abstract

The specificity of the sialic acid-binding lectin from ovine placenta was examined in detail by haemagglutination inhibition assays applying a panel of 32 synthetic sialic acid analogues. The carboxylic acid group is a prerequisite for the interaction with the lectin, the α-anomer of the methyl glycoside is only a little more effective as an inhibitor than the β-anomer and the most potent inhibitor was 9-deoxy-10-carboxylic acid Neu5Ac, followed by 4-oxo-Neu5Ac. In contrast to the majority of known sialic acid-binding lectins, the N-acetyl group of Neu5Ac is not indispensable for binding, neither is the hydroxyl group at C-9 since substitutions at this carbon atom are well tolerated. Furthermore, all sulfur-containing substituents at C-9 enhanced the affinity of the lectin. This is the first sialic acid-binding lectin found to strongly bind thio derivatives.

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References

  1. Lis H, Sharon N, The biochemistry of plants lectins (phytohemagglutinins), Annu Rev Biochem 42, 541–74 (1973).

    Google Scholar 

  2. Goldstein IJ, Hayes CE, The lectins: Carbohydrate-binding proteins of plants and animals, Adv Carbohydr Chem Biochem 35, 127–340 (1978).

    Google Scholar 

  3. Barondes SH, Lectins: Their multiple endogenous cellular functions, Annu Rev Biochem 50, 207–31 (1981).

    Google Scholar 

  4. Doyle R, Keller K, Lectins in diagnostic microbiology, Eur J Clin Microbiol 3, 4–9 (1984).

    Google Scholar 

  5. Lis H, Sharon N, Lectins as molecules and as tools, Annu Rev Biochem 55, 35–67 (1986).

    Google Scholar 

  6. Sharon N, Lis H, Lectins as cell recognition molecules, Science 246, 227–34 (1989).

    Google Scholar 

  7. Nicolson GL, The interactions of lectins with animal cell surfaces, Int Rev Cytol 39, 89–190 (1974).

    Google Scholar 

  8. Fischer E, Khang NQ, Brossmer R, The alpha-galactosyl specific lectin from Artocarpus integrifolia distinguishes between two lymphoma lines with different metastatic potential, Biochem Cell Biol 75, 171–5 (1997).

    Google Scholar 

  9. Varki A, Biological roles of oligosaccharides: All of the theories are correct, Glycobiology 3, 97–130 (1993).

    Google Scholar 

  10. Pilatte Y, Bignon J, Lambré CL, Sialic acids as important molecules in the regulation of the immune system: pathophysiological implications of sialidases in immunity, Glycobiology 3, 201–17 (1993).

    Google Scholar 

  11. Reutter W, KoÈttgen E, Bauer C, Gerok W, In Sialic Acids: Chemistry, Metabolism and Function, edited by Shauer R, (Springer-Verlag, New York, 1982), pp. 263–305.

    Google Scholar 

  12. Yogeeswaran G, Salk PL, Metastatic potential is positively correlated with cell surface sialylation of cultured murine tumor cell lines, Science 212, 1514–6 (1981).

    Google Scholar 

  13. Varki A, Diversity in the sialic acids, Glycobiology 2, 25–40 (1992).

    Google Scholar 

  14. Kelm S, Shauer R, Sialic acids in molecular and cellular interactions, Int Rev Cytol 175, 137–240 (1997).

    Google Scholar 

  15. Marchalonis JJ, Edelman GM, Isolation and characterization of a hemagglutinin from Limulus polyphemus, J Mol Biol 32, 453–65 (1968).

    Google Scholar 

  16. Ravindranath MH, Higa HH, Cooper EL, Paulson JC, Purification and characterization of an O-acetylsialic acid-specific lectin from a marine crab Cancer antennarius, J Biol Chem 260, 8850–6 (1985).

    Google Scholar 

  17. Ahmed H, Chatterjee BP, Kelm S, Shauer R, Purification of a sialic acid-specific lectin from the Indian scorpion Heterometrus granulomanus, Biol Chem Hoppe-Seyler 367, 501–6 (1986).

    Google Scholar 

  18. Mercy PD, Ravindranath H, Purification and characterization of N-glycolylneuraminic acid-specific lectin from Scylla serrata, Eur J Biochem 215, 697–704 (1993).

    Google Scholar 

  19. Vázquez L, Massó F, Rosas P, Montaño LF, Zenteno E, Purification and characterization of a lectin from Macrobrachium rosenbergii (Crustaces, Decapoda) hemolimph, Comp Biochem Physiol 105, 617–23 (1993).

    Google Scholar 

  20. Fischer E, Khang NQ, Letendre G, Brossmer R, A lectin from the Asian horseshoe crab Tachypleus tridentatus: purification, specificity and interaction with tumor cells, Glycoconj J 11, 51–8 (1994).

    Google Scholar 

  21. Miller RL, Collawn JFJ, Fish WW, Purification and macromolecular properties of a sialic acid-specific lectin from the slug Limax flavus, J Biol Chem 257, 7574–80 (1982).

    Google Scholar 

  22. Wagner M, Agglutination of bacteria by a sialic acid-specific lectin of the snail Cepaea hortensis, Acta Histochem 71, 35–9 (1982).

    Google Scholar 

  23. Basu S, Sankar M, Mandal C, A single step purification of a sialic acid binding lectin (AchatininH) from Achatina fulica snail, Mol Cell Biochem 71, 149–57 (1986).

    Google Scholar 

  24. Farthing MJ, Pereira MA, Keusch GT, Description and characterization of a surface lectin from Giardia lamblia, Infect Immun 51, 661–7 (1986).

    Google Scholar 

  25. Babál P, Pindak FF, Wells DJ, Gardner WA Jr, Purification and characterization of a sialic acid-specific lectin from Tritrichomonas mobilensis, Biochem J 299, 341–6 (1994).

    Google Scholar 

  26. Babál P, Pindak FF, Russell LC, Gardner WA Jr, Sialic acid-specific lectin from Tritrichomonas foetus, Biochim Biophys Acta 1428, 106–16 (1999).

    Google Scholar 

  27. Nagata Y, Burger MM, Wheat germ agglutinin. Molecular characteristics and specificity for sugar binding, J Biol Chem 249, 3116–22 (1974).

    Google Scholar 

  28. Shibuya N, Goldstein IJ, Brockaert WF, Nsimba-Lubaki M, Peeters B, Peumans WJ, The elderberry (Sambucus nigra L.) bark lectin recognizes the Neu5Ac(alpha 2-6)Gal/GalNAc sequence, J Biol Chem 262, 1596–601 (1987).

    Google Scholar 

  29. Moch T, Hoschutzcky H, Hacker J, Kroncke KD, Jann K, Isolation and characterization of the alpha-sialyl-beta-2,3-galactosyl-specific adhesin from fimbriated Escherichia coli, Proc Natl Acad Sci 84, 3462–6 (1987).

    Google Scholar 

  30. Hirmo S, Kelm S, Schauer R, Nilsson B, Wadström T, Adhesion of Helicobacter pylori strains to α-2,3-linked sialic acids, Glyconjugate J 13, 1005–11 (1996).

    Google Scholar 

  31. Rogers GN, Herrler G, Paulson JC, Kenk HD, Influenza C virus uses 9-O-acetyl-N-acetylneuraminic acid as a high affinity receptor determinant for attachment to cells, J Biol Chem 261, 5947–51 (1986).

    Google Scholar 

  32. Ahmed H, Gabius HJ, Purification and properties of a Ca2+.-independent sialic acid-binding lectin from human placenta with preferential affinity to O-acetylsialic acids, J Biol Chem 264, 18673–8 (1989).

    Google Scholar 

  33. Ravindranath MH, Paulson JC, Irie RF, Human melanoma antigen O-acetylated ganglioside GD3 is recognised by Cancer antennarius lectin, J Biol Chem 263, 2079–86 (1988).

    Google Scholar 

  34. Sen G, Chowdhury M, Mandal C, O-acetylated sialic acid as a distinct marker for differentiation between several leukemia erythrocytes, Mol Cell Biochem 136, 65–70 (1994).

    Google Scholar 

  35. Mandal C, Sinha D, Sharma V, Bhattacharya DK, O-acetyl sialic acid binding lectin as a probe for detection of subtle change on cell surface induced during acute lymphoblastic leukemia (ALL), Ind J Biochem Biophys 34, 82–6 (1997).

    Google Scholar 

  36. Sinha D, Mandal C, Bhattacharya DK, Development of a simple, blood based lymphoproliferation assay to assess the clinical status of patients with acute lymphoblastic leukemia, Leuk Res 23, 433–9 (1999).

    Google Scholar 

  37. Sinha D, Bhattacharya DK, Mandal C, A colorimetric assay to evaluate the chemotherapeutic response of children with acute lymphoblastic leukemia (AAL) employing achatinin H: A 9-Oacetyl sialic acid binding lectin, Leuk Res 23, 803–9 (1999).

    Google Scholar 

  38. Sinha D, Chatterjee M, Mandal C, O-acetylated sialic acids: Their detection, biological significance and alteration in diseases, Trends Glycosci Glycotech 12, 17–33 (2000).

    Google Scholar 

  39. Iglesias MM, Cymes GD, Wolfenstein-Todel C, A sialic acidbinding lectin from ovine placenta: Purification, specificity and interaction with actin, Glycoconj J 13, 967–76 (1996).

    Google Scholar 

  40. Nowak TP, Haywood PL, Barondes SH, Developmentally regulated lectin in embryonic chick muscle and a myogenic cell line, Biochim Biophys Res Commun 68, 6650–7 (1976).

    Google Scholar 

  41. Meindl P, Tuppy H, Synthetic ketosides of N-acetyl-D-neuraminic acid. (I) Preparation of a series of ketosides susceptible to cleavage by neuraminidase, Monatsh Chemie 96, 802–15 (1965).

    Google Scholar 

  42. Kuhn R, Lutz P, MacDonald DL, Synthese anomerer sialinsäuremethylketoside, Chem Ber 99, 611–7 (1966).

    Google Scholar 

  43. Meindl P. Tuppy H, Synthetic ketosides of N-glycoly-Dneuraminic acid, Monatsh Chemie 97, 1628–47 (1966).

    Google Scholar 

  44. Fujita S, Numata M, Sugimoto M, Tomita K, Ogawa T, Total synthesis of the modified ganglioside de-N-acetyl-GM3 and some analogs, Carbohydr Res 228, 347–70 (1992).

    Google Scholar 

  45. Groβ HJ, Brossmer R, Inhibition of N-acetylneuraminate lyase by N-acetyl-4-oxo-D-neuraminic acid, FEBS Lett 232, 145–7 (1988).

    Google Scholar 

  46. Isecke R, Brossmer R, Synthesis of 5-N-and 9-N-thio-acetylated sialic acids, Tetrahedron 50, 7445–60 (1994).

    Google Scholar 

  47. Brossmer R, Groβ HJ, Fluorescent and photoactivatable sialic acids, Methods Enzymol 247B, 173–93 (1994).

    Google Scholar 

  48. Isecke R, Brossmer R, Synthesis of N-acetyl-9-S-acetyl-9-thioneuraminic acid, N-acetyl-9-thioneuraminic acid, and their methyl alpha-glycosides, Carbohydr Res 274, 303–11 (1995).

    Google Scholar 

  49. Weis WI, Drickamer K, Structural basis of lectin-carbohydrate recognition, Annu Rev Biochem 65, 441–73 (1996).

    Google Scholar 

  50. Stehle T, Yan Y, Benjamin TL, Harrison SC, Structure of murin polyomavirus complexed with an oligosaccharide receptor fragment, Nature 369, 160–3 (1994).

    Google Scholar 

  51. Brossmer R, Wagner M, Fischer E, Specificity of the sialic acidbinding lectin from the snail Cepea hortensis, J Biol Chem 267, 8752–6 (1992).

    Google Scholar 

  52. Fischer E, Brossmer R, Sialic acid-binding lectin: Submolecular specificity and interaction with sialoglycoproteins and tumor cells, Glycoconj J 12, 707–13 (1995).

    Google Scholar 

  53. Kelm S, Brossmer R, Isecke R, Gross HJ, Strenge K, Schauer R, Functional groups of sialic acids involved in binding to siglecs (sialoadhesins) deduced from interactions with synthetic analogues, Eur J Biochem 255, 663–72 (1998).

    Google Scholar 

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Authors and Affiliations

  1. Facultad de Farmacia y Bioquímica, Instituto de Química y Fisicoquímica Biológicas (IQUIFIB) (UBA-CONICET), Junín 956, 1113, Buenos Aires, Argentina

    M. Fernanda Troncoso, M. Mercedes Iglesias & Carlota Wolfenstein Todel

  2. Biochemistry Center, University of Heidelberg, Im Neuenheimer Feld 328, D-69120, Heidelberg, Germany

    Rainer Isecke & Reinhard Brossmer

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  1. M. Fernanda Troncoso
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  2. M. Mercedes Iglesias
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  3. Rainer Isecke
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  4. Carlota Wolfenstein Todel
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  5. Reinhard Brossmer
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Troncoso, M.F., Iglesias, M.M., Isecke, R. et al. Specificity of the binding site of the sialic acid-binding lectin from ovine placenta, deduced from interactions with synthetic analogues. Glycoconj J 17, 705–711 (2000). https://doi.org/10.1023/A:1011022721545

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