Nonreductive release of O-linked oligosaccharides from mucin glycoproteins for structure/function assignments as neoglycolipids: Application in the detection of novel ligands for E-selectin

Glycobiology

Volumn 7, Issue 6, 1997, Pages 861-872

  Chai, Wengang ^a   Feizi, Ten ^a   Yuen, Chun Ting ^a   Lawson, Alexander M ^a  

^a NORTHWICK PARK HOSPITAL   (United Kingdom)

Author keywords

E selectin; Mucins; Neoglycolipids; O linked oligosaccharides; TLC LSIMS

Indexed keywords

ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; GLYCOLIPID; GLYCOPROTEIN; MUCIN; OLIGOSACCHARIDE;

ARTICLE; MASS SPECTROMETRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; BOROHYDRIDES; CARBOHYDRATE SEQUENCE; CATTLE; E-SELECTIN; ETHYLAMINES; GLYCOLIPIDS; HYDROLYSIS; LIGANDS; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; MUCINS; OLIGOSACCHARIDES; OXIDATION-REDUCTION; SALIVARY PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

BOVINAE; SUIDAE;

EID: 0030883428     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/7.6.861     Document Type: Article

References (49)

1. Anderson, B., Rovis, L. and Kabat, E.A. (1972) Immunochemical studies of blood groups. LIII. A study of various conditions of alkaline borohydride degradation on human and hog blood group substances and on known oligosaccharides. Arch. Biochem. Biophys., 148, 304-314.
2. Ballou, C.E. (1954) Alkali-sensitive glycosides. Adv. Carbohydr. Chem., 9, 59-95.
3. Chai, W., Cashmore, G.C., Carruthers, R.A., Stoll, M.S. and Lawson, A.M. (1991) Optimal procedure for combined high-performance thin-layer chromatography/high sensitivity liquid secondary ion mass spectrometry. Biol. Mass. Spectrom., 20, 169-178.
4. Chai, W., Hounsell, E.F., Cashmore, G.C., Rosankiewicz, J.R., Bauer, C.J., Feeney, J., Feizi, T. and Lawson, A.M. (1992a) Neutral oligosaccharides of bovine submaxillary mucin. Eur. J. Biochem., 203, 257-268.
5. 1H-NMR of novel hexasaccharides among the acidic O-linked carbohydrate chains of bovine submaxillary mucin. Eur. J. Biochem., 207, 973-980.
6. Chai, W., Stoll, M.S., Cashmore, G.C. and Lawson, A.M. (1993) Specificity of mild periodate oxidation of oligosaccharide-alditols: relevance to the analysis of the core-branching pattern of O-linked glycoprotein oligosaccharides. Carbohydr. Res., 239, 107-115.
7. Childs, R.A., Drickamer, K., Kawasaki, T., Thiel, S., Mizuochi, T. and Feizi, T. (1989) Neoglycolipids as probes of oligosaccharide recognition by recombinant and natural mannose-binding proteins of the rat and man. Biochem. J., 262, 131-138.
8. Cooper, C.A., Packer, N.P. and Redmond, J.W. (1994) The elimination of O-linked glycans from glycoproteins under non-reducing conditions. Glycoconj. J., 11, 163-167.
9. Coté, R.H. and Morgan, W.T.J. (1956) Some nitrogen-containing disaccharides isolated from human blood-group A substance. Nature, 178, 1171-1172.
10. Cuvillier, O., Wieruszeski, J.-M., Michalski, J.C., and Strecker, G. (1991) Non reductive β-elimination of O-glycosylproteins. In Proceedings of the Meeting of the Nederlandse Vereniging voor de Bestudering van Glycoconjugaten, Cite Scientifique, Villeneuve, d'Ascq, p. 9.
11. Feizi, T. and Childs, R.A. (1994) Neoglycolipids: probes in structure/function assignments to oligosaccharides. Methods Enzymol., 242, 205-217.
12. Feizi, T., Stoll, M.S., Yuen, C.-T., Chai, W. and Lawson, A.M. (1994) Neoglycolipids: probes of oligosaccahride structure, antigenicity, and function. Methods Enzymol., 230, 484-519.
13. Gillece Castro, B.L., Prakobphol, A., Burlingame, A.L., Leffler, H. and Fisher, S.J. (1991) Structure and bacterial receptor activity of a human salivary proline-rich glycoprotein. J. Biol. Chem., 266, 17358-17368.
14. Gottschalk, A. and Graham, E.R.B. (1959) 6-Alpha-D-sialyl-N-acetyl-galactosamine: the neuraminidase-susceptible prosthetic group of bovine salivary mucoprotein. Biochem. Biophys. Acta, 34, 380-391.
15. Hanisch, F.G. and Peter Katalinic, J. (1992) Structural studies on fetal mucins from human amniotic fluid. Core typing of short-chain O-linked glycans. Eur. J. Biochem., 205, 527-535.
16. Iwase, H., Ishii-Karakasa, L. Fujii, E., Hotta, K., Hiki, Y. and Kobayashi, Y. (1992) Analysis of glycolbrm of O-glycan from human myeolma immunoglobulin A1 by gas-phase hydrazinolysis following pyridylamination of oligosaccharides. Anal. Biochem., 206, 202-205.
17. Iyer, R.N. and Carlson, D.M. (1971) Alkaline borohydride degradation of blood group H substance. Arch. Biochem. Biophys., 142, 101-105.
18. Kabat, E.A., Baer, H.H., Bezer, A.E. and Knaub, V. (1948) Immunochemical studies of blood-groups. VII. Chemical changes associated with destruction of blood-group activity and enhancement of the type XIV cross-reactivity by partial hydrolysis of hog and human blood-groups A,B, and substances. J. Exp. Med., 88, 43-57.
19. Kabat, E.A., Bassett, E.W., Pryzansky, K., Lloyd, K.O., Kaplan, M.E. and Layug, E.J. (1965) Immunochemical studies of blood groups XXXIII. The effect of alkaline borohydride and of alkali on blood-group A,B, and H substances. Biochemistry. 4, 1632-1638.
20. Kamerling, J.P. (1989) Mass Spectrometry, Principles, Methods and Applications In Lawson, A.M. (ed.), Walter deGruyter, Berlin, pp. 177-266.
21. Knox, K.W. and Morgan, W.T.J. (1954) The alkaline degradation of human blood-group substances. Biochem. J., 58, v
22. Kuhn, R., Baer, H.H. and Gauhe, A. (1954) Die konstitution der lacto-N-biose I. Chem. Ber., 87, 1553-1560.
23. Kuraya, N. and Hase, S. (1992) Release of O-linked sugar chains from glycoproteins with anhydrous hydrazine and pyridylamination of the sugar chains with improved reaction conditions. J. Biochem., 112, 122-126.
24. Kurosaka, A., Kitagawa, H., Fukui, S., Numata, Y., Nakada, H., Funakoshi, I., Kawasaki, T., Ogawa, T., Iijima, H. and Yamashina, I. (1988) A monoclonal antibody that recognizes a cluster of a disaccharide, NeuAc alpha(2-6)GalNAc, in mucin-type glycoproteins. J. Biol. Chem., 263, 8724-8726.
25. Larkin, M., Ahern, T.J., Stoll, M.S., Shaffer, M., Sako, D., O'Brien, J., Yuen, C.-T., Lawson, A.M., Childs, R.A., Barone, K.M., et al., (1992) Spectrum of sialylated and nonsialylated fuco-oligosaccharides bound by the endothelial-leukocyte adhesion molecule E-selectin. Dependence of the carbohydrate binding activity on E-selectin density. J. Biol. Chem., 267, 13661-13668.
26. Lawson, A.M., Chai, W., Cashmore, G.C. Stoll, M.S., Hounsell, E.F. and Feizi, T. (1990) High-sensitivity structural analyses of oligosaccharide probes (neoglycolipids) by liquid-secondary-ion mass spectrometry. Carbohydr. Res., 200, 47-57.
27. Lloyd, K.O. (1976) In Aspinall, G.O. (ed.), International Review Science: Organic Chemistry. Butterworths, London, pp. 252-281.
28. Lloyd, K.O. and Kabat, E.A. (1969) Immunological studies on blood groups. 40. Scission of oligosaccharides by sodium hydroxide in the presence of sodium borohydride: a model for the degradation of the blood-group substances. Carbohydr. Res., 9, 41-48.
29. Lloyd, K.O., Kabat, E.A., Layug, E.J. and Gruezo, F. (1966) Immunochemical studies on blood groups. 36. Structures of some oligosaccharides produced by alkaline degradation of blood groups A, B, and H substances. Biochemistry, 5, 1489-1501.
30. Marr, X.M.S., Donald, A.S.R., Watkins, W.M. and Morgan, W.T.J. (1967) Molecular and genetic aspects of human blood-group Le(b) specificity. Nature, 215, 1345-1349.
31. Matsushita, M., Endo, Y., Taira, S., Sato, Y., Fujita, T., Ichikawa, N., Nakata, M. and Mizuochi, T. (1996) A novel human serum lectin with collagen- and fibrinogen-like domains that functions as an opsonin. J. Biol. Chem., 271, 2448-2454.
32. Mizuochi, T., Loveless, R.W., Lawson, A.M., Chai, W., Lachmann, P.J., Childs, R.A., Thiel, S. and Feizi, T. (1989) A library of oligosaccharide probes (neoglycolipids) from N-glycosylated proteins reveals that conglutinin binds to certain complex-type as well as high mannose-type oligosaccharide chains. J. Biol. Chem., 264, 13834-13839.
33. Neuberger, A., Marshall, R.D. and Gottschalk, A. (1966) In Gottschalk, A. (ed.), Glycoproteins. Elsevier, New York, pp. 158-186.
34. Painter, T.J. and Morgan, W.T.J. (1961) Partial acid hydrolysis of a mucopolysaccharide without appreciable N-deacetylation. Nature, 191, 39-40.
35. Patel, T., Bruce, J., Merry, A., Bigge, C., Wormald, M., Jaques, A. and Parekh, R. (1993) Use of hydrazine to release in intact and unreduced form both N- and O-linked oligosaccharides from glycoproteins. Biochemistry, 32, 679-693.
36. Pohlentz, G. and Egge, H. (1994) Neoglycolipids of 1-deoxy-1-phosphatidylethanolaminolactitol type: synthesis, structure analysis, and use as probes for characterization of glycosyltransferases. Methods Enzymol., 242, 127-145.
37. Rege, V.P., Painter, T.J., Watkins, W.M. and Morgan, W.T.J. (1964) Isolation of seriologically active fucose-containing oligosaccharides from blood-group H substance. Nature, 203, 360-363.
38. Schiffan, G., Kabat, E.A. and Thompson, W. (1964) Immunochemical studies of blood groups. 30. Cleavage of A,B, and H blood-group substances by alkali. Biochemistry, 3, 113-120.
39. Solis, D., Feizi, T., Yuen, C.-T., Lawson, A.M., Harrison, R.A. and Loveless, R.W. (1994) Differential recognition by conglutinin and mannan-binding protein of N-glycans presented on neoglycolipids and glycoproteins with special reference to complement glycoprotein C3 and ribonuclease B. J. Biol. Chem., 269, 11555-11562.
40. Spillmann, D., Hard, K., Thomas Dates, J., Vliegenthart, J.F., Misevic, G., Burger, M.M. and Finne, J. (1993) Characterization of a novel pyruvylated carbohydrate unit implicated in the cell aggregation of the marine sponge Microciona prolifera. J. Biol. Chem., 268, 13378-13387.
41. Stoll, M.S., Mizuochi, T., Childs, R.A. and Feizi, T. (1988) Improved procedure for the construction of neoglycolipids having antigenic and lectin-binding activities, from reducing oligosaccharides. Biochem. J., 256, 661-664.
42. Stoll, M.S., Hounsell, E.F., Lawson, A.M., Chai, W. and Feizi, T. (1990) Microscale sequencing of O-linked oligosaccharides using mild periodate oxidation of alditols, coupling to phospholipid and TLC-MS analysis of the resulting neoglycolipids [published erratum appears in Eur. J. Biochem. (1990) 192, 813]. Eur. J. Biochem., 189, 499-507.
43. x carbohydrate sequence is recognized by antibody to L5, a functional antigen in early neuronal development. J. Neurochem., 66, 834-844.
44. Tang, P.W. and Feizi, T. (1987) Neoglycolipid micro-immunoassays applied to the oligosaccharides of human milk galactosyltransferase detect blood-group related antigens on both O- and N-linked chains. Carhohydr. Res., 161, 133-143.
45. Tang, P.W., Gooi, H.C., Hardy, H., Lee, H.C. and Feizi, T. (1985) Novel approach to the study of the antigenicities and receptor functions of carbohydrate chains of glycoproteins. Biochem. Biophys. Res. Commun., 132, 474-480.
46. Tsuji, T. and Osawa, T. (1986) Carbohydrate structures of bovine submaxillary mucin. Carbohydr. Res., 151, 391-402.
47. 1H-NMR spectroscopy. Eur. J. Biochem., 127, 21-29.
48. Whistler, R.L. and BeMiller, J.N. (1958) Alkaline degradation of polysaccharides. Adv. Carbohydr. Chem., 13, 289-329.
49. Yuen, C.-T., Lawson, A.M., Chai, W., Larkin, M., Stoll, M.S., Stuart, A.C., Sullivan, F.X., Ahern, T.J. and Feizi, T. (1992) Novel sulfated ligands for the cell adhesion molecule E-selectin revealed by the neoglycolipid technology among O-linked oligosaccharides on an ovarian cystadenoma glycoprotein. Biochemistry. 31, 9126-9131.