Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins - Characterization of the poly LacdiNAc sequence: HSO3(4)(GalNAcβ1-4GlcNAcβ1-3) 1-3GalNAcβ1-4(GlcNAcβ1-3)0-1GlcNAcβ1- 6GalNAc-ol

Glycoconjugate Journal

Volumn 23, Issue 5-6, 2006, Pages 377-399

  Florea, Doina ^a   Maes, Emmanuel ^a   Guérardel, Yann ^a   Page, Adeline ^b   Zanetta, Jean Pierre ^a   Cogalniceanu, Dan ^c   Strecker, Gérard ^a  

^a UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

^b UNIV LILLE   (France)

^c UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

Amphibia; ESI MS MS; Jelly coat; Mucin; NMR; O glycan; Poly LacdiNAc; Triturus alpestris

Indexed keywords

ALDITOL; CAD PROTEIN; CARBOHYDRATE; CARBON 13; DEAMINONEURAMINIC ACID; GLYCAN; GLYCOPROTEIN; HYDROGEN SULFIDE; MUCIN; N ACETYLGALACTOSAMINE; N ACETYLGLUCOSAMINE; N ACETYLNEURAMINIC ACID; N GLYCOLOYLNEURAMINIC ACID; O GLYCAN; OLIGOSACCHARIDE; POLYMER; PROTON; SIALIC ACID; UNCLASSIFIED DRUG;

AMPHIBIA; ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL ANALYSIS; EGG; ELECTROSPRAY MASS SPECTROMETRY; ELECTROSPRAY MASS SPECTROMETRY MASS SPECTROMETRY; FERTILIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SALAMANDER; SPECIES DIFFERENCE; STRUCTURAL BIOINFORMATICS; UTERINE TUBE MUCOSA;

AMPHIBIA; TRITURUS ALPESTRIS;

EID: 84863681574     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-006-6126-4     Document Type: Article

References (32)

1. Inoue, S., Inoue, Y.: Fish glycoproteins, in: Glycoproteins, I.I., Montreuil, J., Vliegenthart, J.F.G., Schachter, H., (eds.) Elsevier Science 143-61 (1997)
2. Wieruszeski, J.M., Michalski, J.C., Montreuil, J., Strecker, G., Peter-Katalinic, J., Egge, H., van Halbeck, H., Mutsears, J.H.G.M., Vliegenthart, J.F.G.: Structure of the monosialyl oligosaccharides derived from salivary gland mucin glycoproteins of the Chinese swiftlet (Genus collocalia). J. Biol. Chem. 262, 6650-57 (1987)
3. Strecker, G.: Amphibian glycoproteins, In: Glycoproteins, I.I., Montreuil, J., Vliegenthart, J.F.G., Schachter, H., (eds.) Elsevier Science 163-72 (1997)
4. Laine, R.A.: A calculation of all possible oligosaccharide isomers both branched and linear yields 1.05 x 10(12) structures for a reducing hexasaccharide: the isomer barrier to development of single-method saccharide sequencing or synthesis systems. Glycobiology 4, 759-67 (1994)
5. Varki, A.: Biological roles of oligosaccharides: all the theories are correct. Glycobiology 3, 97-130 (1993)
6. Zanetta, J.P., Timmerman, P., Leroy, Y.: Gas-liquid chromatography of the heptafluorobutyrate derivatives of the O-methyl glycosides on capillary columns: a method for the quantitative determination of the monosaccharide composition of glycoproteins and glycolipids. Glycobiology 9, 255-66 (1999)
7. Zanetta, J.P., Pons, A., Iwersen, M., Mariller, C., Leroy, Y., Timmerman, P., Schauer, R.: Diversity of sialic acids revealed using gas chromatography/mass spectrometry of heptafluorobutyrate derivatives. Glycobiology 11, 663-76 (2001)
8. 1H-nuclear magnetic resonancespectroscopy of oligosaccharide-alditols released from mucin-type O-glycoproteins. Biological Magnetic Resonance 10, 1-287 (1992)
9. Strecker, G., Wieruszeski, J.M., Michalski, J.C., Alonso, C., Boilly, B., Montreuil, J.: Characterization of Le(x), Le(y) and A Le(y) antigen determinants in KDN-containing O-linked glycan chains from Pleurodeles waltlii jelly coat eggs. FEBS Lett. 298, 39-43 (1992)
10. Strecker, G., Wieruszeski, J.M., Michalski, J.C., Alonso, C., Leroy, Y., Boilly, B., Montreuil, J.: Primary structure of neutral and acidic oligosaccharide-alditols derived from the jelly coat of the Mexican axolotl. Occurrence of oligosaccharides with fucosyl(α1-3)fucosyl(α1-4)-3- deoxy-D-glycero-D-galacto-nonulosonic acid and galactosyl(α1-4) [fucosyl(α1-2)]galactosyl(β1-4)-N-acetylglucosamine sequences. Eur. J. Biochem. 207, 995-1002 (1992)
11. Maes, E., Wieruszeski, J. M., Plancke, Y., Strecker, G.: Structure of three Kdn-containing oligosaccharide-alditols released from oviducal secretions of Ambystoma tigrinum: characterization of the carbohydrate sequence Fuc (α1-5) [Fuc (α1-4)] Kdn (α2-3(6). FEBS Lett. 358, 205-10 (1995)
12. Fontaine, M.D., Wieruszeski, J.M., Plancke, Y., Delplace, F., Strecker, G.: Structure of six 3-deoxy-D-glycero-D-galacto-nonulosonic acid (Kdn)-containing oligosaccharide-alditols released from oviduct secretions of Ambystoma maculatum. Characterization of the sequence fucosyl(α1-2) [fucosyl(α1-3)]fucosyl(α1-4)-3-deoxy-D-glycero-D-galacto- nonulosonic acid. Eur. J. Biochem. 231, 424-33 (1995)
13. Maes, E., Florea, D., Delplace, F., Lemoine, J., Plancke, Y., Strecker, G.: Structural analysis of the oligosaccharide-alditols released by reductive β-elimination from oviducal mucins of Rana temporaria. Glycoconj. J. 14, 127-46 (1997)
14. Lloyd, K.O., Kabat, E.A., Layug, E.J., Gruezo, F.: Immunochemical studies on blood groups. XXXIV. Structures of some oligosaccharides produced by alkaline degradation of blood group A, B, and H substances. Biochemistry 5, 1489-1501 (1966)
15. Lloyd, K.O.: The chemistry and immunochemistry of blood group A, B, H, and Lewis antigens: past, present and future. Glycoconj. J. 17, 531-41 (2000)
16. Florea, D., Maes, E., Haddad, M., Strecker, G.: Structural analysis of the oligosaccharidealditols released from the jelly coat of Rana dalmatina eggs by reductive β-elimination. Biochimie. 84, 611-24 (2002)
17. Mourad, R., Morelle, W., Neveu, A., Strecker, G.: Diversity of O-linked glycosylation patterns between species. Characterization of 25 carbohydrate chains from oviducal mucins of Rana ridibunda. Eur. J. Biochem. 268, 1990-2003 (2001)
18. Coppin, A., Maes, E., Flahaut, C., Coddeville, B., Strecker, G.: Acquisition of species-specific O-linked carbohydrate chains from oviducal mucins in Rana arvalis A case study. Eur. J. Biochem. 266, 370-82 (1999)
19. Guerardel, Y., Kol, O., Maes, E., Lefebvre, T., Boilly, B., Davril, M., Strecker, G.: O-glycan variability of egg-jelly mucins from Xenopus laevis: characterization of four phenotypes that differ by the terminal glycosylation of their mucins. Biochem. J. 352, 449-63 (2000)
20. Nadano, D., Iwasaki, M., Endo, S., Kitajima, K., Inoue, S., Inoue, Y.: A naturally occurring deaminated neuraminic acid, 3-deoxy-D-glycero-D-galacto- nonulosonic acid (KDN). Its unique occurrence at the non reducing ends of oligosialyl chains in polysialoglycoprotein of rainbow trait eggs. J. Biol. Chem. 261, 11550-57 (1986)
21. Knirel, Y., Kocharova, N.A., Shashkov, A.S., Kochetkov, N.K., Mamonotova, V.A., Soloveva, T.F.: Structure of the capsular polysaccharide of Klebsiella ozaenae serotype K4 containing 3-deoxy-D-glycero-D-galacto-nonulosonic acid. Carbohydr. Res. 188, 145-55 (1989)
22. Ziak, M., Qu, B., Zuo, X., Zuber, C., Kanamori, A., Kitajima, K., Inoue, S., Inoue, Y., Roth, J.: Occurrence of poly(alpha2,8-deaminoneuraminic acid) in mammalian tissues: widespread and developmentally regulated but highly selective expression on glycoproteins. Proc. Natl. Acad. Sci. USA 93, 2759-63 (1996)
23. Inoue, S., Lin, S.L., Chang, T., Wu, S.H., Yao, C.W., Chu, T.Y., Troy, F.A. Inoue, Y.: Identification of free deaminated sialic acid (2-keto-3-deoxy-D-glycero-D-galacto-nononic acid) in human red blood cells and its elevated expression in fetal cord red blood cells and ovarian cancer cells. J. Biol. Chem. 273, 27199-204 (1998)
24. Coppin, A., Florea, D., Maes, E., Cogalniceanu, D., Strecker, G.: Comparative study carbohydrate chains released -form the oviducal mucins of the two very closely related amphibian species Bombina bombina and Bombina variegata. Biochimie. 85, 53-64 (2003)
25. Arntzen, J. W.: Some hypotheses on postglacial migrations of the fire-bellied toad, Bombina bombina (Linnaeus) and yellow-bellied toad, Bombina variegata (Linnaeus). J. Biogeog. 2, 339-45 (1978)
26. Hinderlich, S., Stäsche, R., Zeitler, R., Reutter, W.: A bifuctional enzyme catalyzes the first two steps in N-acetylneuraminic acid biosynthesis of rat liver. Purification and characterization of UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase. J. Biol. Chem. 272, 24313-318 (1997)
27. Angata, T., Nakata, D., Matsuda, T., Kitajima, K., Troy, F.A.: Biosynthesis of KDN (2-Keto-3-deoxy-D-glycero-D-galacto-nononic acid). Identification and characterization of a KDN-9-phosphate synthetase activity from trout testis. J. Biol. Chem. 274, 22949-956 (1999)
28. Nakata, D., Close, B.E., Colley, K.J., Matsuda, T., Kitajima, K.: Molecular cloning and expression of the mouse N-acetylneuraminic acid 9-phosphate synthase which does not have deaminoneuraminic acid (Kdn) 9-phosphate synthase activity. Biochem. Biophys. Res. Commun. 273, 642-48 (2000)
29. Lawrence, S.M., Huddleston, K.A., Pitts, L.R., Nguyen, N., Lee, Y.C., Vann, W.F., Coleman, T.A., Betenbaugh, M.J.: Cloning and expression of the human N-acetylneuraminic acid phosphate synthase gene with 2-keto-3-deoxy-D-glycero- D-galacto-nononic acid biosynthetic ability. J. Biol. Chem. 275, 17869-877 (2000)
30. Van den Berg, T.K., Honing, H., Franke, N., van Remoortere, A., Schiphorst, W.E.C.M., Liu, F.-T., Deelder, A.M., Cummings, R.D., Hokke, C.H., van Die, I.: LacdiNAc-glycans constitute a parasite pattern for galectin-3-mediated immune recognition. J. Immunol. 173, 1902-07 (2004)
31. Salo, H., Aitio, O., Ilves, K., Bencomo, E., Toivonen, S., Penttil̈a, L., Niemel̈a, R., Salminen, H., Grabenhorst, E., Renkonen, R., Renkonen, O.: Several polylactosamine-modifying glycosyltransferases also use internal GalNAcβ1-4GlcNAc units of synthetic saccharides as acceptors. Glycobiology 12, 217-28 (2002)
32. Kawar, Z.S., Haslam, S.M., Morris, H.R., Dell, A., Cummings, R.D.: Novel poly-GalNAcβ1-4GlcNAc (LacdiNAc) and fucosylated poly-LacdiNAc N-glycans from mammalian cells expressing β1,4-N-acetylgalactosaminyltransferase and α1,3-fucosyltransferase. J. Biol. Chem. 280, 12810-819 (2005)