Free oligosaccharides with lewis x structure expressed in the segmentation period of zebrafish embryo

Journal of Biochemistry

Volumn 142, Issue 2, 2007, Pages 213-227

  Moriguchi, Kaznnobu ^a   Takemoto, Tatsuya ^a   Aoki, Takafuini ^a   Nakakita, Shin Ichi ^a,b   Natsuka, Shunji ^a   Hase, Sumihiro ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KAGAWA UNIVERSITY   (Japan)

Author keywords

Embryogenesis; Lewis x; Oligosaccharide; Pyridylamination; Zebrafish

Indexed keywords

2 AMINOPYRIDINE; ALPHA 1,3 FUCOSIDASE; ALPHA 1,3 FUCOSYLTRANSFERASE; ALPHA LEVO FUCOSIDASE; EPITOPE; GLUCOSAMINIDASE; LEWIS X ANTIGEN; MANNOSE; N ACETYL BETA GLUCOSAMINIDASE; N ACETYLGALACTOSAMINE; N ACETYLGLUCOSAMINE; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CARBOHYDRATE SYNTHESIS; EMBRYO; EMBRYO SEGMENTATION; ENZYME ACTIVITY; NONHUMAN; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; ZEBRA FISH;

ANIMALS; CARBOHYDRATE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EMBRYO, NONMAMMALIAN; FUCOSYLTRANSFERASES; MANNOSYL-GLYCOPROTEIN ENDO-BETA-N-ACETYLGLUCOSAMINIDASE; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; ZEBRAFISH;

DANIO RERIO;

EID: 35748948991     PISSN: 0021924X     EISSN: None     Source Type: Journal    
DOI: 10.1093/jb/mvm128     Document Type: Article

References (51)

1. Muramatsu, T. (1988) Developmentally regulated expression of cell surface carbohydrates during mouse embryogenesis. J. Cell. Biochem. 36, 1-14
2. Muramatsu, T. (1988) Alterations of cell-surface carbohydrates during differentiation and development. Biochemie 70, 1587-1596
3. Gooi, H.C., Feizi, T., Kapadia, A., Knowles, B.B., Solter, D., and Evans, M.J. (1981) Stage-specific embryonic antigen involves alpha 1 goes to 3 fucosylated type 2 blood group chains. Nature 292, 156-158
4. Fox, N., Damjanov, I., Martines-Hernandez, A., Knowles, B.B., and Solter, D. (1981) Immunohistochemical localization of the early embryonic antigen (SSEA-1) in postimplantation mouse embryos and fetal and adult tissues. Dev. Biol. 83, 391-398
5. Bird, J.M. and Kimber, S.J. (1984) Oligosaccharides containing fucose linked alphad-3) and alpha(1-4) to N-acetylglucosamine cause decompaction of mouse morulae. Dev. Biol. 104, 449-460
6. Fenderson, B.A., Holmes, E.H., Fukushi, Y., and Hakomori, S. (1986) Coordinate expression of X and Y haptens during murine embryogenesis. Dev. Biol. 114, 12-21
7. Fenderson, B.A., Zehavi, U., and Hakomori, S. (1984) A multivalent lacto-N-fucopentaose III-lysyllysine conjugate decompacts preimplantation mouse embryos, while the free oligosaccharide is ineffective. J. Exp. Med. 160, 1591-1596
8. Kageyama, N., Natsuka, S., and Hase, S. (1999) Molecular cloning and characterization of two zebrafish alpha(1,3) fucosyltransferase genes developmentally regulated in embryogenesis. J. Biochem. 125, 838-845
9. Kojima, K., Iwamori, M., Takahashi, S., Kubushiro, K., Nozawa, S., Iizuka, R., and Nagai, Y. (1987) Diplococcal beta-galactosidase with a specificity reacting to beta 1-4 linkage but not to beta 1-3 linkage as a useful exoglycosidase for the structural elucidation of glycolipids. Anal. Biochem. 165, 465-469
10. Paulson, J.C., Prieels, J.P., Glasgow, L.R., and Hill, R.L. (1978) Sialyl- and fucosyltransferases in the biosynthesis of asparaginyl-linked oligosaccharides in glycoproteins. Mutually exclusive glycosylation by beta-galactoside alpha 2 goes to 6 sialyltransferase and N-acetylglucosaminide alpha 1 goes to 3 fucosyltransferase. J. Biol. Chem. 253, 5617-5624
11. Makino, Y., Kuraya, N., Omichi, K., and Hase, S. (1996) Classification of sugar chains of glycoproteins by analyzing reducing end oligosaccharides obtained by partial acid hydrolysis. Anal. Biochem. 238, 54-59
12. Ohashi, S., Iwai, K, Mega, T., and Hase, S. (1999) Quantitation and isomeric structure analysis of free oligosaccharides present in the cytosol fraction of mouse liver: detection of a free disialobiantennary oligosaccharide and glucosylated oligomannosides. J. Biochem. 126, 852-858
13. Yanagida, K., Ogawa, H., Omichi, K., and Hase, S. (1998) Introduction of a new scale into reversed-phase high-performance liquid chromatography of pyridylamino sugar chains for structural assignment. J. Chromatogr. A 800, 187-198
14. Tarutani, M., Norioka, N., Mega, T., Hase, S., and Ikenaka, T. (1993) Structures of sugar chains of hen egg yolk riboflavin-binding protein. J. Biochem. 113, 677-682
15. Gowda, D.C., Schultz, M., Bredehorst, R., and Vogel, C.W. (1992) Structure of the major oligosaccharide of cobra venom factor. Mol. Immunol. 29, 335-342
16. Gowda, D.C., Glushka, J., van Halbeek, H., Thotakura, R.N., Bredehorst, R., and Vogel, C.W. (2001) N-linked oligosaccharides of cobra venom factor contain novel alpha(1-3)galactosylated Le(x) structures. Glycobiology 11, 195-208
17. Geyer, A., Fitzpatrick, T.B., Pawelek, P.D., Kitzing, K., Vrielink, A., Ghisla, S., and Macheroux., P (2001) Structure and characterization of the glycan moiety of L-amino-acid oxidase from the Malayan pit viper Calloselasma rhodostoma. Eur. J. Biochem. 268, 4044-53
18. Streisinger, G. (1995) The Zebrafish Book (Westerfield, M., ed.) University of Oregon Press, Eugene, OR
19. Kuraya, N. and Hase, S. (1992) Analysis of pyridylaminated O-linked sugar chains by two-dimensional sugar mapping. J. Biochem. 112, 122-126
20. Yoshizawa, Z., Sato, T., and Schmid, K. (1966) Hydrazinolysis of alpha-1-acid glycoprotein. Biochem. Biophys. Acta 121, 417-420
21. Yanagida, K., Natsuka, S., and Hase, S. (1999) A pyridylamination method aimed at automatic oligosaccharide analysis of N-linked sugar chains. Anal. Biochem. 274, 229-234
22. Hase, S., Hatanaka, K., Ochiai, K, and Shimizu, H. (1992) Improved method for the component analysis of glycoproteins by pyridylamino sugars purified with immobilized boronic acid. Biosci. Biotech. Biochem. 56, 1676-1677
23. Makino, Y., Omichi, K., and Hase, S. (1998) Analysis of oligosaccharide structures from the reducing end terminal by combining partial acid hydrolysis and a two-dimensional sugar map. Anal. Biochem. 264, 172-179
24. Takemoto, T., Natsuka, S., Nakakita, S., and Hase, S. (2005) Expression of complex-type N-glycans in developmental periods of zebrafish embryo. Glycoconj. J. 22, 21-26
25. Tachibana, Y., Yamashita, K., Kawaguchi, M., Arashima, S., and Kobata, A. (1981) Digestion of asparagine-linked oligosaccharides by endo-beta-N- acetylglucosaminidase in the human skin fibroblasts obtained from fucosidosis patients. J. Biochem. 90, 1291-1296
26. Tachibana, Y., Yamashita, K, and Kobata, A. (1982) Substrate specificity of mammalian endo-beta-N-acetylglucosaminidase: study with the enzyme of rat liver. Arch. Biochem. Biophys. 214, 199-210
27. Ito, K, Okada, Y., Ishida, K., and Minamiura, N. (1993) Evidence for the transglycosylation of complex type oligosaccharides of glycoproteins by endo-beta-N-acetylglucosaminidase HS. J. Biol. Chem. 268, 16074-16081
28. Kato, T., Hatanaka, K., Mega, T., and Hase, S. (1997) Purification and characterization of endo-beta-N-acetylglucosaminidase from hen oviduct. J. Biochem. 122, 1167-1173
29. Muramatsu, T. (1971) Demonstration of an endo-glycosidase acting on a glycoprotein. J. Biol. Chem. 246, 5535-5537
30. Tarentino, A.L. and Maley, F. (1974) Purification and properties of an endo-beta-N-acetylglucosaminidase from Streptomyces griseus. J. Biol. Chem. 249, 811-817
31. Kadowaki, S., Yamamoto, K., Fujisaki, M., Izumi, K., Tochikura, T., and Yokoyama, T. (1990) Purification and characterization of a novel fungal endo-beta-N-acetylglucosaminidase acting on complex oligosaccharides of glycoproteins. Agric. Biol. Chem. 54, 97-106
32. Plummer, T.H. Jr and Tarentino, A. L. (1991) Purification of the oligosaccharide-cleaving enzymes of Flavobacterium meningosepticum. Glycobiology 1, 257-263
33. Yamamoto, K., Kadowaki, S., Fujisaki, M., Kumagai, H., and Tochikura, T. (1994) Novel specificities of Mucor hiemalis endo-beta-N- acetylglucosaminidase acting complex asparagine-linked oligosaccharides. Biosci. Biotechnol. Biochem. 58, 72-77
34. Suzuki, T., Yano, K., Sugimoto, S., Kitajima, K., Lennarz, W.J., Inoue, S., Inoue, Y., and Emori, Y. (2002) Endo-beta-N-acetylglucosaminidase, an enzyme involved in processing of free oligosaccharides in the cytosol. Proc. Natl Acad. Sci. USA 99, 9691-9696
35. Inoue, S., Iwasaki, M., Ishii, K., Kitajima, K., and Inoue, Y. (1989) Isolation and structures of glycoprotein-derived free sialooligosaccharides from the unfertilized eggs of Tribolodon hakonensis, a dace. Intracellular accumulation of a novel class of biantennary disialooligosaccharides. J. Biol. Chem. 264, 18520-18526
36. Nishigaki, M, Yamashita, K., Matsuda, I., Arashima, S., and Kobata, A. (1978) Urinary oligosaccharides of fucosidosis. Evidence of the occurrence of X-antigenic determinant in serum-type sugar chains of glycoproteins. J. Biochem. 84, 823-834
37. Cacan, R., Villers, C., Belard, M., Kaiden, A., Krag, S.S., and Verbert, A. (1992) Different fates of the oligosaccharide moieties of lipid intermediates. Glycobiology 2, 127-136
38. Moore, S.E. and Spiro, E.G. (1994) Intracellular compartmentalization and degradation of free polymannose oligosaccharides released during glycoprotein biosynthesis. J. Biol. Chem. 269, 12715-12721
39. Kmiécik, D., Herman, V., Stroop, C.J., Michalski, J.C., Mir, A.M., Labiau, O., Verbert, A., and Cacan, R. (1995) Catabolism of glycan moieties of lipid intermediates leads to a single Man5GlcNAc oligosaccharide isomer: a study with permeabilized CHO cells. Glycobiology 5, 483-494
40. Saint-Pol, A., Bauvy, C., Codogno, P., and Moore, S.E. (1997) Transfer of free polymannose-type oligosaccharides from the cytosol to lysosomes in cultured human hepatocellular carcinoma HepG2 cells. J. Cell Biol. 136, 45-59
41. Iwai, K, Mega, T., and Hase, S. (1999) Detection of ManSGlcNAc and related free oligomannosides in the cytosol fraction of hen oviduct. J. Biochem. 125, 70-74
42. Cacan, R., Cecchelli, R., and Verbert, A. (1987) Catabolic pathway of oligosaccharide-diphospho-dolichol. Study of the fate of the oligosaccharidic moiety in mouse splenocytes. Eur. J. Biochem. 166, 469-474
43. Cacan, R., Lepers, A., Belard, M., and Verbert, A. (1989) Catabolic pathway of oligosaccharide-diphospho-dolichol. Subcellular sites of the degradation of the oligomannoside moiety. Eur. J. Biochem. 185, 173-179
44. Villers, C., Cacan, R., Mir, A.M., Labiau, O., and Verbert, A. (1994) Release of oligomannoside-type glycans as a marker of the degradation of newly synthesized glycoproteins. Biochem. J. 298, 135-142
45. Iwasaki, M., Seko, A., Kitajima, K., Inoue, Y., and Inoue, S. (1992) Fish egg glycophosphoproteins have species-specific N-linked glycan units previously found in a storage pool of free glycan chains. J. Biol. Chem. 267, 24287-24296
46. Ishii, K, Iwasaki, M., Inoue, S., Kenny, P.T.M., Komura, H., and Inoue, Y. (1989) Free sialooligosaccharides found in the unfertilized eggs of a freshwater trout, Plecoglossus altivelis. A large storage pool of complex-type bi-, tri-, and tetraantennary sialooligosaccharides. J. Biol. Chem. 264, 1623-1630
47. Guérardel, Y., Chang, L.-Y., Maes, E., Huang, C.-J., and Khoo, K.-H. (2006) Glycomic survey mapping of zebrafish identifies unique sialylation pattern. Glycobiology 16, 244-257
48. Thisse, B., Pflumio, S., Thauer, M., Loppin, B., Heyer, V., Degrave, A., Woehl, R., Lux, A., Steffan, T., Charbonnier, X.Q., and Thisse, C. (2001) Expression of the zebrafish genome during embryogenesis (NIH R01 RR15402). ZFIN Direct Data Submission
49. Streit, A., Faissner, A., Gehrig, B., and Schachner, M. (1990) Isolation and biochemical characterization of a neural proteoglycan expressing the L5 carbohydrate epitope. J. Neurochem. 55, 1494-1506
50. Roberts, C., Platt, N., Streit, A., Schachner, M., and Stern, C.D. (1991) The L5 epitope: an early marker for neural induction in the chick embryo and its involvement in inductive interactions. Development 112, 959-970
51. Streit, A., Yuen, C.T., Loveless, R.W., Lawson, A.M., Finne, J., Schmitz, B., Feizi, T., and Stern, C.D. (1996) The Le(x) carbohydrate sequence is recognized by antibody to L5, a functional antigen in early neural development. J. Neurochem. 66, 834-44