Regiospecific glycosidase-assisted synthesis of lacto-N-biose I (Galβ1- 3GlcNAc) and 3'-sialyl-lacto-N-biose I (NeuAcα2-3Galβ1-3GlcNAc)

European Journal of Biochemistry

Volumn 267, Issue 4, 2000, Pages 942-949

  Vetere, Amedeo ^a,c   Miletich, Marinella ^d   Bosco, Marco ^b   Paoletti, Sergio ^d  

^a AREA Science Park   (Italy)

^b Area Science Park Padriciano 99   (Italy)

^c UNIVERSITY OF TRIESTE   (Italy)

^d NONE

Author keywords

3' sialyl lacto N biose I; Lacto N biose I; Lewis(a); Sialyl Lewis; Transglycosylation

Indexed keywords

GLYCOSIDASE; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CONTROLLED STUDY; ENZYME MECHANISM; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; TRYPANOSOMA CRUZI; XANTHOMONAS;

ACETYLGLUCOSAMINE; BETA-GALACTOSIDASE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLYCOPROTEINS; GLYCOSIDE HYDROLASES; GLYCOSYLATION; HYDROGEN-ION CONCENTRATION; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR WEIGHT; N-ACETYLNEURAMINIC ACID; NEURAMINIDASE; STEREOISOMERISM; XANTHOMONAS;

TRYPANOSOMA; TRYPANOSOMA CRUZI; XANTHOMONAS; XANTHOMONAS AXONOPODIS PV. MANIHOTIS;

EID: 0033975998     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.2000.01068.x     Document Type: Article

References (46)

1. 1. Yamashita, K., Totani, K., Iwaki, Y., Kuroki, M., Matsuoka, Y., Endo, T. & Kobata, A. (1989) Carbohydrate structures of nonspecific cross-reactions antigen-2, a glycoprotein purified from meconium as an antigen cross-reactions with anticarcinoembryonic antigen antibody. J. Biol. Chem. 264, 17873-17881.
2. 6) as human tumor-associated antigen. J. Biol. Chem. 266, 8439-8446.
3. 3. Nozawa, S., Narisawa, S., Kojima, K., Sakayori, M., Jizuka, R., Mochizuki, H., Yamauchi, T., Iwamori, M. & Nagai, Y. (1989) Human monoclonal antibody (HMST-1) against lacto-series type I chain and expression of the chain in uterine endometrial cancers. Cancer Res. 49, 6401-6406.
4. 4. Terashima, M., Kato, K. & Osawa, T. (1982) An antibody to lacto-N-biose I. Carboydr. Res. 110, 345-350.
5. 5. Lasky, L.A. (1992) Selectins: interpreters of cell-specific carbohydrate information during inflammation. Science 258, 964-969.
6. 6. Nelson, R.M., Dolich, S., Aruffo, A., Cecconi, O. & Bevilacqua, M.P. (1993) Higher-affinity oligosaccharide ligands for E-selectin. J. Clin. Invest. 91, 1157-1166.
7. 7. Kuhn, R., Gauhe, A. & Baer, H.H. (1954) Lacto-N-tetraose and its relation to the fucose-containing oligosaccharides of human milk. Chem. Ber. 87, 289-300.
8. 8. Flowers, H.M. & Jeanloz, R.W. (1963) The synthesis of 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-glucose. J. Org. Chem. 28, 1377-1379.
9. 9. Lemieux, R.U. & Driguez, H. (1975) The chemical synthesis of 2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-3-O-(β-D-galactopyranosyl)-D-glucose. The Lewis a blood-group antigenic determinant. J. Am. Chem. Soc. 97, 4063-4068.
10. 10. Lemieux, R.U., Bundle, D.R. & Baker, D.A. (1975) The properties of a "synthetic" antigen related to the human blood-group Lewis a. J. Am. Chem. Soc. 97, 4076-4083.
11. 11. Jain, R.K., Locke, R.D. & Matta, K. (1993) A convenient synthesis of lacto-N-biose I [β-D-Galp-(1→3)-beta;-D-GlcpNAc] linked oligosaccharides from phenyl O-(tetra-O-acetyl-β-D-galactopyranosyl)-(1→3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside. Carbohydr. Res. 241, 165-176.
12. 12. Hanessian, S. (1997) Preparative Carbohydrate Chemistry. Marcel Dekker Inc., New York, USA.
13. 13. Ichikawa, Y, Look, G.C. & Wong, C.-H. (1992) Enzyme-catalyzed oligosaccharide synthesis. Anal. Biochem. 202, 215-238.
14. 14. Wong, C.-H., Halcomh, R.L., Ichikawa, Y. & Kajimoto, T. (1995) Enzymes in organic synthesis: application to the problems of carbohydrate recognition (part. 2). Angew. Chem. Int. Ed. Engl. 34, 521-546.
15. 15. Nilsson, K.G.I. (1987) A simple strategy for changing the regioselectivity of glycosidase-catalysed formation of disaccharides. Carbohydr. Res. 167, 95-103.
16. 16. Nilsson, K.G.I. (1988) A simple strategy for changing the regioselectivity of glycosidase-catalysed formation of disaccharides: part II. Enzymatic synthesis in situ of various acceptor glycosides. Carbohydr. Res. 180, 53-59.
17. 17. Nilsson, K.G.I. (1988) Enzymatic synthesis of oligosaccharides. Trends Biotech. 6, 256-264.
18. 18. Cote, G.L. & Tao, B.Y. (1990) Oligosaccharide synthesis by enzymatic transglycosylation. Glycoconj. J. 7, 145-162.
19. 19. Bucke, C. & Rastall, R.A. (1990) Synthesising sugars by enzymes in reverse. Chem. Britain 26, 675-678.
20. 20. Usui, T. (1992) Regioselective synthesis of useful oligosaccharide by glycosidase. Trends Glycosci. Glycotech. 4, 116-122.
21. 21. Vetere, A. & Paoletti, S. (1996) High-yield synthesis of N-acetyllactosamine by regioselective transglycosylation. Biochem. Biophys. Res. Comm. 219, 6-13.
22. 22. Vetere, A., Ferro, S., Bosco, M., Cescutti, P. & Paoletti, S. (1997) All-transglycolytic synthesis and characterization of sialyl (α2-3) galactosyl(β1-4)xylosyl-, p-nitrophenyl (β1-), an oligosaccharide derivative related to glycosaminoglycan biosynthesis. Eur. J. Biochem. 247, 1083-1090.
23. 23. Crout, D.H. & Vic, G. (1998) Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis. Curr. Opin. Chem Biol. 2, 98-111.
24. 24. Vetere, A., Novelli, L. & Paoletti, S. (1999) On the effect of the aglycon structure of three aryl β-D-galactosides on the yield and the regioselectivity of the transglycolytic synthesis of N-acetyllactosamine. J. Carbohydr. Chem. 18, 515-521.
25. 25. Smith, L.E., Uemura, H. & Eichinger, D. (1996) Isolation and expression of an open reading frame encoding sialidase from Trypanosoma rangelii. Mol. Biochem. Parasit. 79, 21-33.
26. 26. Shupp, J.M., Travis, S.E., Price, L.B., Shand, R.F. & Keim, P. (1995) Rapide bacterial permeabilization reagent useful for enzyme assays. Biotechniques 19, 18-20.
27. 27. Vetere, A. & Paoletti, S. (1996) Complete synthesis of 3'-sialyl-N-acetyllatosamine by regioselective transglycosylation. FEBS Lett. 399, 203-206.
28. 28. Schenkman, S., Pontes de Carvalho, L. & Nussenzweig, V. (1992) Trypanosoma cruzi trans-sialidase and neuraminidase activities can be mediated by the same enzymes. J. Exp. Med. 175, 567-575.
29. 29. Palcic, M. (1994) Glycosyltransferases in glycobiology. Methods Enzymol. 230, 300-316.
30. 30. Honda, S., Akao, E., Suzuki, S., Okuda, M., Kakehi, K. & Nakamura, J. (1989) High-performance liquid chromatography of reducing carbohydrates as strongly ultraviolet-absorbing and electrochemically sensitive 1-phenyl-3-methyl-5-pyrazolone derivatives. Anal. Biochem. 180, 351-357.
31. 31. López, R. & Fernández-Mayoralas, A. (1992) Controlling yield and regioselectivity in the enzymatic synthesis of β-D-galactopyranosyl-β-D-xylopyranosides. Tetrahedron Lett. 33, 5449-5452.
32. 32. López, R. & Fernández-Mayoralas, A. (1994) Enzymatic β-galactosidation of modified monosaccharides: study of the enzyme selectivity for the acceptor and its application to the synthesis of disaccharides. J. Org. Chem. 59, 737-745.
33. 33. Sabesan, S., Duus, J.Ø., Fukunaga, T., Bolk, K. & Ludvigsen, S. (1991) NMR and conformational analysis of ganglioside GD1a. J. Am. Chem. Soc. 113, 3236-3246.
34. 34. Bermam, E. (1983) Determination of the structure of three oligosaccharides from normal human urine by using 60 MHz, Carbon-13 nuclear magnetic resonance spectroscopy. Carbohydr. Res. 118, 9-20.
35. 35. Hedbys, L., Johansson, E., Mosbach, K., Larsson, P.-O., Gunnarsson, A., Svensson, S. & Lönn, H. (1989) Synthesis of Galβ1-3GlcNAc and Galβ1-3GlcNAcβ-SEt by enzymatic method comprising the sequential use of β-galactosidases from bovine testes and Escherichia coli. Glycoconj. J. 6, 161-168.
36. 36. Fujimoto, H. (1997) Regioselective synthesis of β-D-Gal-(1→3)-D-GlcNAc using β-galactosidase from Xanthomonas manihotis. J. Carbohydr. Chem. 16, 967-970.
37. 37. Derensy-Dron, D., Krzewìnski, F., Brassart, C. & Bouquelet, S. (1999) β-1,3-Galactosyl-N-acetylhexosamine phosphorylase from Bifido-bacterium bifidum DSM 20082: characterization, partial purification and relation to mucin degradation. Biotechnol. Appl. Biochem. 29, 3-10.
38. 13C NMR spectroscopy. J. Am. Chem. Soc. 108, 2068-2080.
39. 39. Nilsson, K.G.I. (1989) Enzymatic synthesis of di-and tri-saccharide glycosides, using glycosidases and β-D-galactoside 2-α-sialyltrans-ferase. Carbohydr. Res. 188, 9-17.
40. 40. Vandekerckhove, F., Schenkman, S., Pontes de Carvalho, L., Tomlinson, S., Kiso, M., Yoshida, M., Hasegawa, A. & Nussenzweig, V. (1992) Substrate specificity of the Trypanosoma cruzi trans-sialidase. Glycobiology 2, 541-548.
41. 41. Colli, W. (1993) Trans-sialidase: a unique enzyme enzyme activity discovered in the protozoan Trypanozoma cruzi. FASEB J. 7, 145-162.
42. 42. Scudder, P.R., Doom, J.P., Chuenkova, M., Manger, I.D. & Pereira, M.E.A. (1993) Enzymatic characterization of β-D-galactoside α2,3-trans-sialidase from Trypanosoma cruzi. J. Biol. Chem. 268, 9886-9891.
43. 43. Nishimura, S.-I., Lee, K.B., Matsuoka, K. & Lee, Y.C. (1994) Chemoenzymatic preparation of glycoconjugate polymer having a sialyloligosaccharide: NeuAcα(2-3)Galβ(1-4)GlcNAc. Biochem. Biophys. Res. Comm. 189, 249-254.
44. 44. Lee, K.B. & Lee, Y.C. (1994) Transfer of modified sialic acid by Trypanosoma cruzi trans-sialidase for attachment of functional groups to oligosaccharide. Anal Biochem. 216, 358-364.
45. 45. Takahashi, N., Lee, K.B., Nakagawa, H., Tsukamoto, Y., Kawamura, Y., Li, Y.-T. & Lee, Y.C. (1995) Enzymatic sialylation of N-linked oligosaccharides using an α-(2,3)-specific trans-sialidase from Trypanosoma cruzi: structural identification using a three-dimensional elution mapping technique. Anal Biochem. 230, 333-342.
46. 46. Ribeirão, M., Pereira-Chioccola, V.L., Eichinger, D., Rodrigues, M.M. & Schenkman, S. (1997) Temperature differences for transglycosylation and hydrolysis reaction reveal an acceptor binding site in the catalytic mechanism of Trypanosoma cruzi trans-sialidase. Glycobiology 7, 1237-1246.