Partial purification and substrate specificity of heparan sulfate α-N-acetylglucosaminyltransferase I: Synthesis, NMR spectroscopic characterization and in vitro a assays of two aryl tetrasaccharides

Glycobiology

Volumn 7, Issue 5, 1997, Pages 587-595

  Fritz, Timothy A ^a,b   Agrawal, Pawan K ^a   Esko, Jeffrey D ^a,c   Krishna, N Rama ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Heparan sulfate N acetylglucosaminyltransferase I; Linkage tetrasaccharide; NMR; Proteoglycan; Substrate specificity; Synthesis

Indexed keywords

N ACETYLGLUCOSAMINYLTRANSFERASE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CARBOHYDRATE SYNTHESIS; CHO CELL; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME PURIFICATION; ENZYME SPECIFICITY; IN VITRO STUDY; LIVER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RAT; REACTION ANALYSIS;

ANIMALIA;

EID: 0030833811     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/7.5.587-c     Document Type: Article

References (35)

1. Agrawal, P.K. (1992) NMR spectroscopy in structure elucidation of oligosaccharides and glycosides. Phytochemistry, 32, 3307-3330.
2. Agrawal, P.K., Jain, D.C., Gupta, R.K. and Thakur, R.S. (1985). Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins. Phytochemistry, 27, 2479-2496.
3. Bax, A. and Davis, D.G. (1985) MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson., 65, 355-360.
4. Bax, A., Griffey, R.H. and Hawkins, B.L. (1983) Correlation of proton and nitrogen-15 chemical shifts by multiple quantum NMR. J. Magn. Reson., 55, 301-315.
5. Choe, B.-Y., Ekborg, G.C., Roden, L., Harvey, S.C. and Krishna, N.R. (1991) High-resolution NMR and molecular modeling studies on complex carbohydrates: Characterization of O-β-D-Gal-(1 → 3)O-β-D-Gal-(1 → 4)-O-β-D-Xyl-(1 → 0)-L-Ser, a carbohydrat-protein linkage region fragment from connective tissue proteoglycans. J. Am. Chem. Soc., 131, 3743-3749.
6. 1H NMR assignments of synthetic glycopeptides from the carbohydrate-protein linkage region of serglycins. Glycoconjugate J., 13, 599-607.
7. Esko, J.D., Stewart, T.E. and Taylor, W.H. (1985) Animal cell mutants defective in glycosaminoglycan biosynthesis. Proc. Natl. Acad. Sci. USA, 82, 3197-3201.
8. Esko, J.D. and Zhang, L. (1996) Influence of core protein sequence on glycosaminoglycan assembly. Curr. Opin. Struct. Biol.,6, 663-670.
9. Fransson, L.-A., Karlsson, P. and Schmidtchen, A. (1992) Effect of cycloheximide, brefeldin A, suramin, heparin and primaquine on proteoglycan and glycosaminoglycan biosynthesis in human embryonic skin fibroblasts. Biochim. Biophys. Acta, 1137, 287-297.
10. Fritz, T.A., Lugemwa, F.N., Sarkar, A.K. and Esko, J.D. (1994a) Biosynthesis of heparan sulfate on β-D-xyloside depends on aglycone structure. J. Biol. Chem., 269, 300-307.
11. Fritz, T.A., Gabb, M.M., Wei, G. and Esko, J.D. (1994b) Two N-acetylglucosaminyltransferases catalyze the biosynthesis of heparan sulfate. J. Biol. Chem., 269, 28809-28814.
12. Haltiwanger, R.S., Blomberg, M.A. and Hart, G.W. (1992) Glycosylation of nuclear and cytoplasmic proteins-purification and characterization of a uridine diphospho-N-acetyl glucosamine: polypeptide β-N-acetylglucosaminyltransferase. J. Biol. Chem., 267, 9005-9013.
13. Kjellen, L. and Lindahl, U. (1991) Proteoglycans: structures and Interactions. Annu. Rev. Biochem., 60, 443-475.
14. Krishna, N.R., Choe, B.-Y. Prabhakaran, M., Ekborg, G.C., Roden, L. and Harvey, S.C. (1990) Nuclear magnetic resonance and molecular modeling studies on O-β-D-galactopyranosyl-(1 → 4)-O-β-D-xylopyranosyl-(1 → 0)-L-serine, a carbohydrate-protein linkage region fragment from connective tissue proteoglycans. J. Biol. Chem., 256, 18256-18262.
15. Leelavathi, D.E., Estes, L.W., Feingold, D.S. and Lombardi, B. (1970) Isolation of a golgi-rich fraction from rat liver Biochim. Biophys. Acta, 211, 124-138.
16. Liu, J., Desai, U.R., Han, X.-J., Toida, T. and Linhardt, R.J. (1995) Strategy for the sequence analysis of heparin. Glycobiology, 5, 765-774.
17. Lowry, O.H., Rosebrough, N.J., Farr, A.L. and Randall, R.J. (1951) Protein measurement with the folin phenol reagent. J. Biol. Chem., 193, 265-275.
18. Lugemwa, F.N. and Esko, J.D. (1991) Estradiol β-D-xyloside, an efficient primer for heparan sulfate biosynthesis. J. Biol. Chem., 266, 6674-6677.
19. 1H NMR analysis using a nano-NMR probe indicates the presence of a terminal α-GalNAc residue copping 4-methylumbelliferyl-β-D-xylosides J. Biol. Chem., 270, 9154-9163.
20. 1H coupling constants in proteins. Biochem. Biophys. Res. Commun., 113, 967-974.
21. Meldal, M. and Bock, K. (1994) A general approach to the synthesis of O- and N-linked glycopeptides. Glycoconjugate J., 11, 59-63.
22. Nilsson, M., Westaman, J. and Svahn, C.-M. (1993) Synthesis of tri- and tetrasaccharides present in the linkage region of heparin and heparan sulphate. J. Carbohydr. Chem., 12, 23-37.
23. Nilsson, S., Lonn, H. and Norberg, T. (1991) Synthesis of two tumor-associated oligosaccharides: di- and trifucosylated para-lacto-N-hexaose. J. Carbohydr. Chem., 10, 1023-1048.
24. Rio, S., Beau, J.-M. and Jacquinet, J.-C. (1991) Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans. Carbohydr. Res., 219, 71-90.
25. Rohrmann, K., Niemann, R. and Buddecke, E. (1985) Two N-acetylgalactosaminyltransferase are involved in the biosynthesis of chondroitin sulfate. Eur. J. Biochem., 148, 463-469.
26. Shively, J.E. and Conrad, H.E. (1976) Formation of anhydrosugars in the chemical depolymerization of heparin. Biochemistry, 15, 3932-3942.
27. Sugahara, K., Masuda, M., Harada, T., Yamashina, I., de Waard, P. and Vliegenthart, J.F.G. (1991) Structural studies on sulfated oligosaccharides derived from carbohydrate-protein linkage region of chondroitin sulfate proteoglycans of whale cartilage. Eur. J. Biochem., 202, 805-811.
28. Sugahara, K., Yamada, S., Yoshida, K., de Waard, P. and Vliegenthart, J.F.G. (1992) A novel sulfated structure in the carbohydrate-protein linkage region isolated on porcine intestinal heparin. J. Biol. Chem., 267, 1528-1533.
29. Sugahara, K., Tohno-oka, R., Yamada, S., Khoo, K.-H. and Dell, A. (1994) Structural studies on the oligosaccharides isolated from bovine kidney heparan sulphate and characterization of bacterial heparitinases used as substrates. Glycobiology, 4, 535-544.
30. Uhlin-Hansen, L. and Yanagishita, M. (1993) Differential effect of brefeldin A on the biosynthesis of heparan sulfate and chondroitin/dermatan sulfate proteoglycans in rat ovarian granulosa cell in culture. J. Biol. Chem. 268, 17370-17376.
31. van Halbeek, H., Dorland, L., Veldink, G.A., Vliegenthart, J.F.G., Garegg, P.J., Noorberg, T. and Lindberg, B. (1982) A 500 MHz proton-magnetic-resonance study of several fragments of the carbohydrate-protein linkage region commonly occuring in proteoglycans. Eur. J. Biochem., 127, 1-6.
32. Zhang, L. and Esko, J.D. (1994) Amino acid determinants that drive heparan sulfate assembly in a proteoglycan. J. Biol. Chem., 269, 19295-19299.
33. Zhang, L. and Esko, J.D. (1995) Accumulation of a pentasaccharide terminating in α-N-acetylglucosamine in an animal cell mutant defective in heparan sulfat biosynthesis. J. Biol. Chem., 270, 12557-12562.
34. Zhang, L., David, G. and Esko, J.D. (1995) Repetitive ser-gly sequences enhance heparan sulfate assembly in proteoglycans. J. Biol. Chem., 270, 27127-27135.
35. Zsiska, M. and Meyer, B. (1991) Synthesis of β-D-GlcA-(1 → 3)-β-D-Gal disaccharide with 4- and 6- sulfate groups and 4,6-disulfate groups. Carbohydr. Res., 215, 279-292.