Some key experimental features of a modular synthesis of heparin-like oligosaccharides

European Journal of Organic Chemistry

Volumn , Issue 17, 2003, Pages 3308-3324

  De Paz, José Luis ^a   Ojeda, Rafael ^a   Reichardt, Niels ^a   Martín Lomas, Manuel ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

Carbohydrates; Glycosylation; Heparin; Oligosaccharides; Synthesis design

Indexed keywords

DISACCHARIDE; HEPARIN DERIVATIVE; OLIGOSACCHARIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL REACTION; ELECTRIC POTENTIAL; MOLECULAR SIZE; PROTEIN ASSEMBLY; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 0042786019     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (50)

1. [1a] J. L. de Paz, J. Angulo, J. M. Lassaletta, P. M. Nieto, M. Redondo-Horcajo, R. M. Lozano, G. Giménez-Gallego, M. Martín-Lomas, ChemBioChem 2001, 2, 673-685.
2. [1b] R. Ojeda, J. Angulo, P. M. Nieto, M. Martín-Lomas, Can. J. Chem. 2002, 80, 917-936.
3. [1c] R. Lucas, J. Angulo, P. M. Nieto, M. Martín-Lomas, Org. Biomol. Chem. 2003, 1, 2253-2266.
4. S. Faham, R. J. Linhardt, D. C. Rees, Curr. Opin. Struct. Biol. 1998, 8, 578-586.
5. I. Capila, R. J. Linhardt, Angew. Chem. Int. Ed. 2002, 41, 390-412.
6. U. Lindahl, L. Thunberg, G. Bäckström, J. Riesenfeld, K. Nordling, I. Björk, J. Biol. Chem. 1984, 259, 2368-2376.
7. B. Casu, U. Lindahl, Adv. Carbohydr. Chem. Biochem. 2001, 57, 159-206.
8. B. Mulloy, M. J. Forster, Glycobiology 2000, 10, 1147-1156.
9. J. Angulo, R. Ojeda, J. L. de Paz, R. Lucas, P. M. Nieto, R. M. Lozano, G. Giménez-Gallego, M. Martín-Lomas, ChemBioChem, manuscript submitted.
10. J. Angulo, P. M. Nieto, M. Martín-Lomas, Chem. Commun. 2003, 1512-1513.
11. K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531.
12. P. J. Kociénski, Protecting groups, Thieme, Stuttgart, New York, 1994.
13. H. A. Orgueira, A. Bartolozzi, P. Schell, R. E. J. N. Litjens, E. Palmacci, P. H. Seeberger, Chem. Eur. J. 2003, 9, 140-169.
14. [12a] J. Tamura, Trend. Glycosci. Glycotechnol. 1994, 6, 29-50.
15. [12b] J. Tamura, Trend. Glycosci. Glycotechnol 2001, 13, 65-88.
16. [13a] C. A. A. van Boeckel, M. Petitou, Angew. Chem. Int. Ed. Engl. 1993, 32, 1671-1690 and references therein.
17. [13b] M. Petitou, J. Herault, A. Bernat, P. Driguez, P. Duchaussoy, J. Lormeau, J. Herbert, Nature 1999, 398, 417-422.
18. [13c] M. Petitou, P. Duchaussoy, P. Driguez, J. Herault, J. Lormeau, J. Herbert, Biorg. Med. Chem. Lett. 1999, 9, 1155-1160.
19. [13d] M. Petitou, P. Duchaussoy, P. Driguez, J. Herault, J. Lormeau, J. Herbert, Biorg. Med. Chem. Lett. 1999, 1161-1166.
20. [13e] M. Petitou, A. Imberty, P. Duchaussoy, P. A. Driguez, M. L. Ceccato, F. Gourvenec, P. Sizun, J. P. Herault, S. Perez, J. M. Herbert, Chem. Eur. J. 2001, 7, 858-873.
21. [13f] P. D. J. Grootenhuis, C. A. A. van Boeckel, J. Am. Chem. Soc. 1991, 113, 2743-2747.
22. [13g] N. Sakairi, J. E. M. Basten, G. A. van der Marel, C. A. A. van Boeckel, J. H. van Boom, Chem. Eur. J. 1996, 2, 1007-1013.
23. [13h] M. Petitou, P. Duchaussoy, G. Jaurand, F. Gourvenec, I. Lederman, J. Strassel, T. Barzu, B. Crepon, J. Herault, J. Lormeau, A. Bernat, J. M. Herbert, J. Med. Chem. 1997, 40, 1600-1607.
24. [13i] M. Petitou, P. Duchaussoy, P. Driguez, G. Jaurand, J. Herault, J. Lormeau, C. A. A. van Boeckel, J. Herbert, Angew. Chem. Int. Ed. 1998, 37, 3009-3014.
25. A. Lubineau, O. Gavard, J. Alais, D. Bonnaffé, Tetrahedron Lett. 2000, 41, 307-311.
26. [15a] J. C. Jacquinet, M. Petitou, P. Duchaussoy, I. Lederman, J. Choay, G. Torri, P. Sinay, Carbohydr. Res. 1984, 130, 221-241.
27. [15b] R. Ojeda, J. L. de Paz, M. Martín-Lomas, J. M. Lassaletta, Synlett 1999, 8, 1316-1318.
28. [16a] A. Vasella, C. Witzig, J. L. Chiara, M. Martín-Lomas, Helv. Chim. Acta 1991, 74, 2073-2077.
29. [16b] P. B. Alper, S. C. Hung, C.-H. Wong, Tetrahedron Lett. 1996, 37, 6029-6032.
30. [16c] P. T. Nyffeler, C. H. Liang, K. M. Koeller, C.-H. Wong, J. Am. Chem. Soc. 2002, 124, 10773-10778.
31. [17a] M. M. Palme, A. Vasella, Helv. Chim. Acta 1995, 78, 959-969.
32. [17b] S.-Y. Luo, S. R. Thopate, C.-Y. Hsu, S.-C. Hung, Tetrahedron Lett. 2002, 43, 4889-4892.
33. [18a] C. Murakata, T. Ogawa, Carbohydr. Res. 1992, 234, 75-91.
34. [18b] A. Toepfer, R. R. Schmidt, J. Carbohydr. Chem. 1993, 12, 809-822.
35. M. Martín-Lomas, M. Flores-Mosquera, J. L. Chiara, Eur. J. Org. Chem. 2000, 1547-1562.
36. R. R. Schmidt, W. Kinzy, Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
37. B. La Ferla, L. Lay, M. Guerrini, L. Poletti, L. Panza, G. Russo, Tetrahedron 1999, 55, 9867-9880.
38. M. López de la Paz, G. Ellis, M. Pérez, J. Perkins, J. Jiménez-Barbero, C. Vicent, Eur. J. Org. Chem. 2002, 840-855.
39. R. R. Schmidt, A. Toepfer, Tetrahedron Lett. 1991, 32, 3353-3356.
40. P. J. Garegg, in Preparative Carbohydrate Chemistry (Ed.: S. Hanessian), Marcel Dekker, New York, 1997, 53-67.
41. T. B. Grindley, Adv. Carbohydr. Chem. Biochem. 1998, 53, 17-142.
42. P. Baumhof, R. Mazitschek, A. Giannis, Angew. Chem. Int. Ed. 2001, 40, 3672-3674.
43. H. A. Orgueira, A. Bartolozzi, P. Schell, P. H. Seeberger, Angew. Chem. Int. Ed. 2002, 41, 2128-2131.
44. K. C. Nicolaou, C. A. Veale, C. K. Hwang, J. Hutchinson, C. V. C. Prasad, W. W. Ogilwie, Angew. Chem. Int. Ed. Engl. 1991, 30, 299-303.
45. S. A. Abbas, A. H. Haines, Carbohydr. Res. 1975, 39, 358-363.
46. [30a] K. C. Nicolaou, R. A. Daines, T. K. Chakraborty, J. Am. Chem. Soc. 1987, 109, 2208-2210.
47. [30b] S. Masamune, J. W. Ellingboe, W. Choy, J. Am. Chem. Soc. 1982, 104, 5526-5528.
48. [30c] K. C. Nicolaou, S. E. Webber, Synthesis 1986, 453-461.
49. [30d] K. C. Nicolaou, S. P. Seitz, M. R. Pavia, J. Am. Chem. Soc. 1981, 103, 1222-1224.
50. T. Tabeur, F. Machetto, J. M. Mallet, P. Duchaussoy, M. Petitou, P. Sinaÿ, Carbohydr. Res. 1996, 281, 253-276.