Oxidation of glycosphingolipids under basic conditions: Synthesis of glycosyl 'serine acids' as opposed to 'ceramide acids'. Precursors for neoglycoconjugates with increased ligand binding affinity

Biochemistry

Volumn 38, Issue 33, 1999, Pages 10885-10897

  Mylvaganam, M ^a   Meng, L J ^b   Lingwood, C A ^a,b  

^a HOSPITAL FOR SICK CHILDREN RESEARCH INSTITUTE   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMANTADINE DERIVATIVE; CERAMIDE DERIVATIVE; GALACTOSYLCERAMIDE; GLOBOTRIAOSYLCERAMIDE; GLYCOCONJUGATE; GLYCOLIPID; GLYCOSPHINGOLIPID; HYDROCARBON; HYDROXYBUTYRIC ACID; IODINE DERIVATIVE; LACTOSYLCERAMIDE; OLIGOSACCHARIDE; OXYGEN DERIVATIVE; PERMANGANATE POTASSIUM; PROPIONIC ACID DERIVATIVE; SERINE DERIVATIVE; SODIUM DERIVATIVE; SPHINGOLIPID; SPHINGOSINE DERIVATIVE; TERT BUTYL ALCOHOL; VEROTOXIN;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; LIGAND BINDING; OXIDATION; PH; PRIORITY JOURNAL; STOICHIOMETRY; SYNTHESIS;

ACYLATION; ANIMALS; BACTERIAL TOXINS; BINDING SITES; CARBOHYDRATE SEQUENCE; CARBONATES; CATTLE; CERAMIDES; GLYCOCONJUGATES; GLYCOSPHINGOLIPIDS; HUMANS; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PERIODIC ACID; POTASSIUM; SERINE; SHEEP; SHIGA-LIKE TOXIN I; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 0033578398     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi990669m     Document Type: Article

References (24)

1. Hakomori, S. (1986) Sci. Am. 254, 40-53.
2. Hakomori, S. (1983) in Sphingolipid Biochemistry (Kanfer, J. N., and Hakomori, S., Eds.) Plenum Press, New York.
3. Stults, C. L. M., Sweeley, C. H., and Macher, B. A. (1989) Methods Enzymol. 179, 167-214.
4. Kiarash, A., Boyd, B., and Lingwood, C. A. (1994) J. Biol. Chem. 269, 11138-11146.
5. Sonnino, S., Kirschner, G., Ghidoni, R., Aquotti, D., and Tettamanti, G. (1985) J. Lipid Res. 26, 248-257.
6. Picking, W. D. (1993) Biochem. Biophys. Res. Commun. 195, 1153-1158.
7. Pagano, R., and Martin, O. (1988) Biochemistry 27, 4439-4445.
8. Young, W. W. J., Laine, R. A., and Hakomori, S. (1979) J. Lipid Res. 20, 275-278.
9. Laine, R., Yogeeswaren, G., and Hakomori, S. (1974) J. Biol. Chem. 249, 4460-4466.
10. MacDonald, D. L., Pat, L., and Hakomori, S. (1980) J. Lipid Res. 21, 642-645.
11. Seeberger, P. H., Bilodeau, M. T., and Danishefsky, S. J. (1997) Aldrichim. Acta 30, 75-92.
12. Mylvaganam, M., and Lingwood, C. A. (1999) J. Biol. Chem. 274, 20725-20732.
13. Lemieux, R. U., and von Rudloff, E. (1955) Can. J. Chem. 33, 1701-1709.
14. Boyd, B., Zhiuyan, Z., Magnusson, G., and Lingwood, C. A. (1994) Eur. J. Biochem. 223, 873-878.
15. Boyd, B., and Lingwood, C. A. (1989) Nephron 51, 207-210.
16. Head, S., Ramotar, K., and Lingwood, C. A. (1990) Infect. Immun. 58, 1532-1537.
17. Yamakawa, T., Irie, R., and Iwanaga, M. (1960) J. Biochem. 48, 490-497.
18. Boulanger, J., Petric, M., Lingwood, C. A., Law, H., Roscoe, M., and Karmali, M. (1990) J. Clin. Microbiol. 28, 2830-2833.
19. Lingwood, C. A., Law, H., Richardson, S., Petric, M., Brunton, J. L., DeGrandis, S., and Karmali, M. (1987) J. Biol. Chem. 262, 8834-8839.
20. Hsu, F.-F., Bohrer, A., and Turk, J. (1998) Biochim. Biophys. Acta 1392, 202-216.
21. Nyholm, P. G., Magnusson, G., Zheng, Z., Norel, R., Binnington-Boyd, B., and Lingwood, C. A. (1996) Chem. Biol. 3, 263-275.
22. Nyholm, P.-G., Brunton, J. L., and Lingwood, C. A. (1995) Int. J. Biol. Macromol. 17, 199-205.
23. Pascher, I., and Sundell, S. (1977) Chem. Phys. Lipids 20, 175-191.
24. Kuduk, S. D., Schwarz, J. B., Chen, X. T., Glunz, P. W., Sames, D., Ragupathi, G., Livingston, P. O., and Danishefsky, S. J. (1998) J. Am. Chem. Soc. 120, 12474-12485.