First synthesis of heparan sulfate tetrasaccharides containing both N-acetylated and N-unsubstituted glucosamine - Search for putative 10E4 epitopes

ChemBioChem

Volumn 7, Issue 12, 2006, Pages 1856-1858

  Hamza, Daniel ^a   Lucas, Ricardo ^a   Feizi, Ten ^b   Chai, Wengang ^b   Bonnaffé, David ^a   Lubineau, André ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Glycosylation; Heparan sulfate; Oligosaccharides; Prion pathogenesis; Regioselectivity

Indexed keywords

EPITOPE; GLUCOSAMINE; HEPARAN SULFATE; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY 10E4; OLIGOSACCHARIDE;

ANTIGENICITY; ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY;

ACETYLATION; CARBOHYDRATE SEQUENCE; EPITOPES; GLUCOSAMINE; HEPARITIN SULFATE; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NITROGEN; OLIGOSACCHARIDES;

SCRAPIE PRION;

EID: 33845409771     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200600356     Document Type: Article

References (37)

1. J. M. Whitelock, R. V. Iozzo, Chem. Rev. 2005, 105, 2745-2764.
2. a) I. Capila, R. J. Linhardt, Angew. Chem. 2002, 114, 426-450;
3. Angew. Chem. Int. Ed. 2002, 41, 390-412;
4. b) H. Lortat-Jacota, A. Grosdidier, A. Imberty, Proc. Natl. Acad. Sci. USA 2002, 99, 1229-1234.
5. a) M. Petitou, B. Casu, U. Lindhal, Biochimie 2003, 85, 83-89;
6. b) S. Sarrazin, D. Bonnaffé, A. Lubineau, H. Lortat-Jacob, J. Biol. Chem. 2005, 280, 37558-37564;
7. c) A. Lubineau, H. Lortat-Jacob, O. Gavard, S. Sarrazin, D. Bonnaffé, Chem. Eur. J. 2004, 10, 4265-4282;
8. d) M. Guerrini, T. Agulles, A. Bisio, M. Hricivini, L. Lay, A. Naggi, L. Poletti, L. Sturiale, G. Torri, B. Casu, Biochem. Biophys. Res. Commun. 2002, 292, 222-230;
9. e) J. Angulo, R. Ojeda, J. L. De Paz, R. Lucas, P. M. Nieto, R. -M Lozano, M. Redondo-Horcajo, G. Gimenez-Gallego, M. Martin-Lomas, ChemBioChem 2004, 5, 55-61;
10. f) A. Canales, J. Angulo, R. Ojeda, M. Bruix, R. Fayos, R. Lozano, G. Gimenez-Gallego, M. Martin-Lomas, P. M. Nieto, J. Jimenez-Barbero, J. Am. Chem. Soc. 2005, 127, 5778-5779.
11. M. Petitou, C. A. A. van Boeckel, Angew. Chem. 2004, 116, 3180-3196;
12. Angew. Chem. Int. Ed. 2004, 43, 3118-3133.
13. P. A. McBridge, M. I. Wilson, P. Eikelenboom, A. Tunstall, M. E. Bruce, Exp. Neurol. 1998, 149, 447-454.
14. C. Leteux, W. G. Chai, K. Nagai, C. G. Herbert, A. M. Lawson, T. Feizi, J. Biol. Chem. 2001, 276, 12 539-12 545.
15. a) U. R. Desai, H. Wang, R. J. Linhardt, Biochemistry 1993, 32, 8140-8145;
16. b) U. R. Desai, H. M. Wang, R. J. Linhardt, Arch. Biochem. Biophys. 1993, 306, 461-468.
17. a) F. Cheng, K. Mani, J. van den Born, K. Ding, M. Belting, L.-A. Fransson, J. Biol. Chem. 2002, 277, 44431-44439;
18. b) K. Mani, F. Cheng, S. Sandgren, J. van den Born, B. Havsmark, K. Ding, L.-A. Fransson, Glycobiology 2004, 14, 599-607;
19. c) J. van den Born, K. Salmivirta, T. Henttinen, N. Ostman, T. Ishimaru, S. Miyaura, K. Yosida, M. Salmivirta, J. Biol. Chem. 2005, 280, 20516-20523.
20. M. Goedert, R. Jakes, M. G. Spillantini, M. Hasegawa, M. J. Smith, R. A. Crowther, Nature 1996, 383, 550-553.
21. a) W. Chai, C. Leteux, C. Westling, T. Feizi, Biochemistry 2004, 43, 8590-8599;
22. b) T. Toida, H. Yoshida, H. Toyoda, I. Koshiishi, T. Imanari, R. E. Hileman, J. R. Fromm, R. J. Linhardt, Biochem. J. 1997, 322, 499-506;
23. c) J. van den Born, K. Gunnarsson, M. A. Bakker, L. Kjellen, M. Kusche-Gullberg, M. Maccarana, J. H. Berden, U. Lindahl, J. Biol. Chem. 1995, 270 31303-31309.
24. C. Westling, U. Lindahl, J. Biol. Chem. 2002, 277, 49247-49255.
25. a) J. D. C. Codée, H. S. Overkleeft, G. A. van der Marel, C. A. A. van Boeckel, Drug Discovery Today Technol. 2004, 1, 317-326;
26. b) G. J. S. Lohman, P. H. Seeberger, J. Org. Chem. 2004, 69, 4081-4093.
27. a) C. A. A. van Boeckel, M. Petitou, Angew. Chem. 1993, 105, 1741- 1760;
28. Angew. Chem. Int. Ed. 1993, 32, 1671-1690;
29. b) J. L. de Paz, M. Martin Lomas, Eur. J. Org. Chem. 2005, 1849-1858;
30. c) J. L. de Paz, R. Ojeda, N. Reichardt, M. Martin-Lomas, Eur. J. Org. Chem. 2003, 3308-3324.
31. a) R. Lucas, D. Hamza, A. Lubineau, D. Bonnaffé, Eur. J. Org. Chem. 2004, 2107-2117;
32. b) L. Liao, F. I. Auzanneau, J. Org. Chem. 2005, 70, 6265-6273.
33. H. Paulsen, R. Lebuhn, Carbohydr. Res. 1984, 130, 85-101.
34. J. J. Oltvoort, C. A. A. van Boeckel, J. H. Koning, J. H. van Boom, Synthesis 1981, 305-308.
35. 1H NMR analyses. Collision Induced Dissociation MS/MS sequence analyses showed nonacetylated GlcN residues located internally between the two hexuronic acids, thus confirming the location of the N-acetyl group at the reducing terminus. See Supporting Information.
36. a) A. Dilhas, D. Bonnaffé, Tetrahedron Lett. 2004, 45, 3643-3645;
37. b) O. Gavard, J. Alais, A. Bascou, Y. Hersant, V. Duverger, A. Dilhas, D. Bonnaffe, Eur. J. Org. Chem. 2003, 3603-3620.