Solid-phase synthesis of oligonucleotide glycoconjugates bearing three different glycosyl groups: Orthogonally protected bis(hydroxymethyl)-N,N′- bis(3-hydroxypropyl)malondiamide phosphoramidite as key building block

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7609-7615

  Katajisto, Johanna ^a   Heinonen, Petri ^a   Lönnberg, Harri ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

AMINOLYSIS; OLIGONUCLEOTIDES;

ALDEHYDES;

4,4' DIMETHOXYTRITYL DERIVATIVE; AMINOPROPANOL; BIS(HYDROXYMETHYL) N,N' BIS(3 HYDROXYPROPYL)MALONDIAMIDE PHOSPHORAMIDITE; DIETHYL O,O' (METHOXYMETHYLENE)BIS(HYDROXYMETHYL)MALONATE; GALACTOSE; GLUCOSE; GLYCOCONJUGATE; GLYCOSYL 6 O PHOSPHORAMIDITE; HYDROXYL GROUP; LEVULINYL DERIVATIVE; MANNOSE; N,N DIISOPROPYLPHOSPHORAMIDOUS ACID; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PROPANOLAMINE DERIVATIVE; SILANE DERIVATIVE; TERT BUTYLDIPHENYLSILYL DERIVATIVE; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

AMINOLYSIS; AMMONOLYSIS; ARTICLE; COMBINATORIAL CHEMISTRY; CONJUGATION; COVALENT BOND; ELECTROSPRAY MASS SPECTROMETRY; GEL CHROMATOGRAPHY; GLYCOSYLATION; MELTING POINT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID; SYNTHESIS;

CATALYSIS; GLYCOCONJUGATES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS;

EID: 6344277035     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048984o     Document Type: Article

References (59)

1. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
2. Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321-327.
3. Mammen, M.; Choi, S.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2755-2794.
4. Sharon, N.; Lis, H. Science 1989, 246, 227-234.
5. Taylor, M. E.; Bezouška, K.; Drickamer, K. J. Biol. Chem. 1992, 267, 1719-1726.
6. Dimick, S. M.; Powell, S. C.; McMahon, S. A.; Moothoo, D. N.; Naismith, J. H.; Toone, E. J. J. Am. Chem. Soc. 1999, 121, 10286-10296.
7. (a) Sreedhara, A.; Cowan, J. A. J. Biol. Inorg. Chem. 2001, 6, 166-172.
8. (b) Hanessian, S.; Qiu, D.; Prabhanjan, H.; Reddy, G. V.; Lou, B. Can. J. Chem. 1996, 74, 1738-1747.
9. (c) Hansen, H. C.; Haataja, S.; Finne, J.; Magnusson, G. J. Am. Chem. Soc. 1997, 119, 6974-6979.
10. (d) Hanessian, S.; Prabhanjan, H. Synlett, 1994, 868-870.
11. (e) Lehmann, J.; Scheuring, M. Carbohydr. Res. 1995, 276, 57-74.
12. (f) Lehmann, J.; Weitzel, U. P. Carbohydr. Res. 1996, 294, 65-94.
13. (g) Veeneman, G. H.; Van der Hulst, R. G. A.; Van Boeckel, C. A. A.; Philipsen, R. L. A.; Ruigt, G. S. F.; Tonnaer, J. A. D. M.; Van Delft, T. M. L.; Konings, P. N. M. Bioorg. Med. Chem. Lett. 1995, 5, 9-14.
14. (h) Lindhorst, T. K.; Dubber, M.; Krallmann-Wenzel, U.; Ehlers, S. Eur. J. Org. Chem. 2000, 2027-2034.
15. (i) Liu, B.; Roy, R. J. Chem. Soc., Perkin Trans. 1 2001, 8, 773-779.
16. (j) Frison, N.; Taylor, M. E.; Soilleux, E.; Bousser, M.; Mayer, R.; Monsigny, M.; Drickamer, K.; Roche, A. J. Biol. Chem. 2003, 278, 23922-23929.
17. (k) Sato, K.; Hada, N.; Takeda, T. Tetrahedron Lett. 2003, 44, 9331-9335.
18. (l) Kalovidouris, S. A.; Blixt, O.; Nelson, A.; Vidal, S.; Turnbull, W. B.; Paulson, J. C.; Stoddart, J. F. J. Org. Chem. 2003, 68, 8485-8493.
19. (a) Roy, R.; Zanini, D.; Meunier, S. J.; Romanowska, A. J. Chem. Soc., Chem. Commun. 1993, 1869-1872.
20. (b) Pagé, D.; Zanini, D.; Roy, R. Bioorg. Med. Chem. 1996, 4, 1949-1961.
21. (c) Ježek, J.; Velek, J.; Vepřek, P.; Velková, V.; Trnka, T.; Pecka, J.; Ledvina, M.; Vondrášek, J.; Písačka, M. J. Pept. Sci. 1999, 5, 46-55.
22. (d) Lindhorst, T. K.; Dubber, M. Org. Lett. 2001, 3, 4019-4022.
23. (e) Roy, R.; Kim; J. M. Tetrahedron 2003, 59, 3881-3893.
24. Virta, P.; Katajisto, J.; Niittymäki, T.; Lönnberg, H. Tetrahedron 2003, 59, 5137-5174.
25. (a) Fulton, D. A.; Stoddart, J. F. J. Org. Chem. 2001, 66, 8309-8319.
26. (b) André, S.; Kaltner, H.; Furuike, T.; Nishimura, S.; Gabius, H. Bioconjugate Chem. 2004, 15, 87-98.
27. (a) Manning, D. D.; Strong, L. E.; Hu, X.; Beck, P. J.; Kiessling, L. L. Tetrahedron 1997, 53, 11937-11952.
28. (b) Mann, D. A.; Kanai, M.; Maly, D. J.; Kiessling, L. L. J. Am. Chem. Soc. 1998, 120, 10575-10582.
29. (c) Strong, L. E.; Kiessling, L. L. J. Am. Chem. Soc. 1999, 121, 6193-6196.
30. (d) Owen, R. M.; Gestwicki, J. E.; Young, T.; Kiessling, L. L. Org. Lett. 2002, 4, 2293-2296.
31. (a) Patel, A.; Lindhorst, T. K. Eur. J. Org. Chem. 2002, 79-86.
32. (b) Tanaka, H.; Amaya, T.; Takahashi, T. Tetrahedron Lett. 2003, 44, 3053-3057.
33. (a) Schmidt, M.; Dobner, B.; Nuhn, P. Synlett 2000, 1157-1159.
34. (b) Katajisto, J.; Karskela, T.; Heinonen, P.; Lönnberg, H. J. Org. Chem. 2002, 67, 7995-8001.
35. Wang, L.; Prakash, R. K.; Stein, C. A.; Koehn, R. K.; Ruffner, D. E. Antisense Nucleic Acid Drug Dev. 2003, 13, 169-189.
36. (a) Midoux, P.; Mendes, C.; Legrand, A.; Raimond, J.; Mayer, R.; Monsigny, M.; Roche, A. C. Nueleic Acids Res. 1993, 21, 871-878.
37. (b) Liang, W.; Shi, X.; Deshpande, D.; Malanga, C. J.; Rojanasakul, Y. Biochim. Biophys. Acta 1996, 1279, 227-234.
38. (c) Erbacher, P.; Roche, A. C.; Monsigny, M.; Midoux, P. Biochim. Biophys. Acta 1997, 1324, 27-36.
39. (a) Bonfils, E.; Depierreux, C.; Midoux, P.; Thuong, N. T.; Monsigny, M.; Roche, A. C. Nucleic Acids Res. 1992, 20, 4621-4629.
40. (b) Biessen, E. A. L.; Vietsch, H., Rump, E. T.; Fluiter, K.; Kuiper, J.; Bijsterbosch, M. K.; Van Berkel, T. J. C. Biochem. J. 1999, 340, 783-792.
41. Maier, M. A.; Yannopoulos, C. G.; Mohamed, N.; Roland, A.; Fritz, H.; Mohan, V.; Just, G.; Manohara, M. Bioconjugate Chem. 2003, 14, 18-29.
42. Hangeland, J. J.; Flesher, J. E.; Deamond, S. F.; Lee, Y. C.; Ts'O, P. O. P. Antisense Nucleic Acid Drug Dev. 1997, 7, 141-149.
43. Adinolfi, M.; Barone, G.; De Napoli, L.; Guariniello, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1999, 40, 2607-2610.
44. Sando, S.; Matsui, K.; Niinomi, Y.; Sato, N.; Aoyama, Y. Bioorg. Med. Chem. Lett. 2003, 13, 2633-2636.
45. (a) Hunziker, J. Bioorg. Med. Chem. Lett. 1999, 9, 201-204.
46. (b) Matsuura, K.; Hibino, M.; Yamada, Y.; Kobayashi, K. J. Am. Chem. Soc. 2001, 123, 357-358.
47. (c) De Kort, M.; Ebrahimi, E.; Wijsman, E. R.; Van der Marel, G. A.; Van Boom, J. H. Eur. J. Chem. 1999, 2337-2344.
48. (a) Akhtar, S.; Routledge, A.; Patel, R. Tetrahedron Lett. 1995, 36, 7333-7336.
49. (b) Sheppard, T. L.; Wong, C.; Joyce, G. F. Angew. Chem., Int. Ed. 2000, 39, 3660-3663.
50. Dubber, M.; Fréchet, J. M. J. Bioconjugate Chem. 2003, 14, 239-246.
51. Katajisto, J.; Virta, P.; Lönnberg, Bioconjugate Chem. 2004, 15, 890-896.
52. Guzaev, A.; Salo, H.; Azhayev, A.; Lönnberg, H. Bioconjugate Chem. 1996, 7, 240-248.
53. Du, Y.; Zhang, M.; Kong, F. Org. Lett. 2000, 2, 3797-3800.
54. Wahlström, J. L.; Ronald, R. C. J. Org. Chem. 1998, 63, 6021-6022.
55. Scaringe, S. A.; Wincott, F. E.; Caruthers, M. H. J. Am. Chem. Soc. 1998, 120, 11820-11821.
56. Atkinson, T.; Smith, M. Oligonucleotide Synthesis: A Practical Approach; IRL Press: Oxford, U.K., 1984; p 48.
57. Westman, E.; Strömberg, R. Nueleic Acids Res. 1994, 22, 2430-2431.
58. 2) in DMF in 30 min. Dahl, B. J.; Bjergarde, K.; Henriksen, L.; Dahl, O. Acta Chem. Scand. 1990, 44, 639-641.
59. Koga, M.; Wilk, A.; Moore, M. F.; Scremin, C. L.; Zhou, L.; Beaucage, S. L. J. Org. Chem. 1995, 60, 1520-1530.