'Linkage region' sequences of heparins and heparan sulfates: Detection and quantification by nuclear magnetic resonance spectroscopy

Analytical Biochemistry

Volumn 274, Issue 1, 1999, Pages 50-58

  Iacomini, M ^a   Casu, B ^a   Guerrini, M ^a   Naggi, A ^a   Pirola, A ^a   Torri, G ^a  

^a Istituto di Ricerche Chimiche e Biochimiche G Ronzoni   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOSACCHARIDES; POLYSACCHARIDES; SULFUR COMPOUNDS;

13C NMR SIGNALS; 13C NMR SPECTRUM; ACID HYDROLYZATES; CARBOHYDRATE CHAINS; DETECTION AND QUANTIFICATIONS; GLYCOSAMINOGLYCANS; HEPARAN SULFATES; PEPTIDE CHAIN;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

GLYCOSAMINOGLYCAN; HEPARAN SULFATE; HEPARIN; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ASSAY;

EID: 0033215151     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1006/abio.1999.4230     Document Type: Article

References (35)

1. Lane D. A., Björk I., Lindahl U. Heparin and Related Polysaccharides. 1992;Plenum Press, New York.
2. Lindahl U., Lidholt K., Spillmann D., Kjellén L. Heparin: More than anticoagulation. Thrombosis Res. 75:1994;1-32.
3. Robinson H. C., Horner A. A., Höök M., Ögren S., Lindahl U. J. Biol. Chem. 253:1978;6687-6693.
4. Casu B. Structure and biological activities of heparin. Adv. Carbohydr. Chem. Biochem. 43:1985;51-134.
5. European Patent, 1990, Low sulfate oligosaccharide fraction derived from heparin or heparan sulfate, for inhibition of capillary endothelial cell proliferation and angiogenesis. EP394971A (Kabivitrum).
6. Hanhenberger R., Jakobson Å M., Ansari A., Wehler T., Svahn C. M., Lindahl U. Low-sulfated oligosaccharides derived from heparan sulfate inhibit normal angiogenesis. Glycobiology. 3:1993;567-573.
7. Lindahl U., Cifonelli J. A., Lindahl B., Rodén L. The role of serine in the linkage of heparin to protein. J. Biol. Chem. 240:1965;2817-2820.
8. Lindahl U., Rodén L. The role of galactose and xylose in the linkage of heparin to protein. J. Biol. Chem. 240:1965;2821-2826.
9. Lindahl U. Further characterization of the heparin-protein linkage region. Biochim. Biophys. Acta. 130:1966;368-382.
10. Sugahara K., Yamada S., Yoshida K., de Waard P., Vliegenthart J. F. G. A novel sulfated structure in the carbohydrate-protein linkage region isolated from porcine intestinal heparin. J. Biol. Chem. 267:1993;1528-1533.
11. Sugahara K., Tsuda H., Yoshida K., Yamada S., de Beer T., Vliegenthart J. F. G. Structure determination of the octa- and decasaccharide sequences isolated from the carbohydrate-protein linkage region of porcine intestinal heparin. Biol. Chem. 270:1995;22914-22923.
12. Liu J., Desai U. R., Han X. J., Toida T., Linhardt R. J. Strategy for the sequence analysis of heparin. Glycobiology. 5:1995;765-774.
13. Taylor R. L., Shively J. E., Conrad H. E., Cifonelli J. A. Uronic acid composition of heparins and heparan sulfates. Biochemistry. 12:1973;3633-3637.
14. Kusche M., Torri G., Casu B., Lindahl U. Biosynthesis of heparin. Availability of glucosaminyl 3-O-sulfation sites. J. Biol. Chem. 265:1990;7292-7300.
15. Casu B., Diamantini G., Fedeli G., Mantovani M., Oreste P., Pescador R., Porta R., Prino G., Torri G. Retention of antilipemic activity by non-anticoagulant periodate-oxidized heparins. Arzneim. Forsch. (Drug Res.). 36:1986;635-642.
16. 1H nuclear magnetic resonance spectroscopy. Anal. Biochem. 223:1994;135-141.
17. Casu B., Guerrini M., Naggi A., Torri G., De-Ambrosi L., Boveri G., Gonella S., Cedro A., Ferro L., Lanzarotti E., Paternò M., Attolini M., Valle M. G. Characterization of sulfation patterns of beef and pig mucosal heparins by nuclear magnetic resonance spectroscopy. Arzneim. Forsch. (Drug Res.). 46:1996;472-477.
18. Dubois M., Gilles K. A., Hamilton I. K., Rebers P. A., Smith F. Determination of sugars and related substances. Anal. Biochem. 28:1956;350-355.
19. Brown A. K. Reaction of sugars with orcinol. Arch. Biochem. 11:1946;269-274.
20. Dabrowski J. Two-dimensional proton magnetic resonance spectroscopy. Methods Enzymol. 179:1989;122-156.
21. Homans J. W. Oligosaccharide conformations: Application of NMR and energy calculations. Prog. NMR Spectrosc. 22:1990;55-81.
22. Kay L. E., Keifer P., Saarinen T. Pure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity. Am. Chem. Soc. 114:1992;10663-10669.
23. 13C-HSQC and HSQC-TOCSY to the alpha-subunit of human chorionic gonadotropin. FEBS Lett. 348:1994;1-6.
24. Stott K., Keeler J., Shaks J. One-dimensional NOE experiments using pulse field gradients. J. Magn. Res. 125:1997;302-324.
25. 13C NMR spectral assignments of the major sequences of twelve systematically modified heparin derivatives. Carbohydr. Res. 294:1996;15-27.
26. Lindberg B., Rodén L., Silvander B. G. Carbohydr. Res. 2:1966;398-406.
27. 1H NMR spectra of heparin and heparan sulfate. Carbohydr. Res. 170:1987;151-165.
28. Huckerby T. N., Nieduszynski I. A. Proton chemical-shift assignment in the NMR spectra of heparan and heparin. Carbohydr. Res. 103:1982;141-145.
29. Perlin, A. S., and Casu, B.1982Spectroscopic methods. inThe Polysaccharides (Aspinall, G. O., Ed.), Vol. 1, pp. 133-193, Academic Press, New York.
30. 1H-NMR spectroscopy as a tool in the structural analysis of carbohydrates related to glycoproteins. Adv. Carbohydr. Chem. Biochem. 41:1983;209-274.
31. Casu B., Guerrini M., Naggi A., Torri G., Hricovini M., Lay L., Panza L., Russo G. Abstr. EUROCARB VIII. 1995;B59.
32. Krishna R. N. R., Choe B.-Y., Prabhakaran M., Ekborg G. C., Rodén L., Harvey S. C. Nuclear magnetic resonance and molecular modeling studies on O-β-d-galactopyranosyl-(1→4)-O-β-d-xylopyranosyl-(1→O)-l- serine, a carbohydrate-protein linkage region fragment from connective tissue glycosaminoglycans. J. Biol. Chem. 265:1990;18256-18262.
33. Van Halbeek H., Dorland L., Veldnink G. A., Vliegenthart J. F. G., Garegg J., Norberg T., Lindberg B. A 500-MHz proton magnetic resonance study of several fragments of the carbohydrate-protein linkage region commonly occurring in proteoglycans. Eur. J. Biochem. 127:1982;1-6.
34. 13C NMR analyses and titration data from variously desulfated and periodate-oxidized heparins. Biochem. J. 175:1978;299-309.
35. Casu B., Naggi A., Oreste P., Torri G., Pangrazzi A., Maggi M., Abbadini M., Donati M. B. Bleeding associated with heparin contaminants. Lancet. 1987;1088.