Conjugation of nucleosides and oligonucleotides by [3+2] cycloaddition

Journal of Organic Chemistry

Volumn 73, Issue 1, 2008, Pages 287-290

  Jawalekar, Anup M ^a   Meeuwenoord, Nico ^b   Cremers, J G O ^a   Overkleeft, Herman S ^b   Van Der Marel, Gijs A ^b   Rutjes, Floris P J T ^a   Van Delft, Floris L ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CONDENSATION; COPPER; CYCLOADDITION; DIMERS; SYNTHESIS (CHEMICAL);

ADENOSINE DIMERS; CONJUGATION; NUCLEOSIDES; OLIGONUCLEOTIDE STRANDS;

OLIGONUCLEOTIDES;

ALKYNE DERIVATIVE; DIMER; NUCLEOSIDE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONJUGATION; CYCLOADDITION; ELECTROCHEMISTRY; FLUORESCENCE; HYBRIDIZATION; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

ALKYNES; CATALYSIS; COPPER; CYCLIZATION; MOLECULAR STRUCTURE; NUCLEOSIDES; OLIGONUCLEOTIDES;

EID: 37549012482     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702023s     Document Type: Article

References (47)

1. (a) Zamecnik, P. C.; Stephenson, M. L. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 280-284.
2. (b) Stephenson, M. L.; Zamecnik, P. C. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 285-288.
3. (a) Muthiah, M. Antisense Nucleic Acid Drug. Dev. 2002, 12, 103-128.
4. (b) Aboul-Fadl, T. Curr. Med. Chem. 2005, 12, 2193-2214.
5. (a) Bennett, C. F. Biochem. Pharmacol. 1998, 55, 9-19.
6. (b) Jarvis L. M. Chem. Eng. News 2006, 13-18.
7. Corey, D. R. Nature Chem. Biol. 2007, 3, 8-11.
8. (a) Gray, G. D.; Basu, S.; Wickstrom, E. Biochem. Pharmacol. 1997, 53, 1465-1476.
9. (b) Stein, C. A.; Tonkinson, J. L.; Zhang. L. M.; Yakubov, L.; Gervasoni, J.; Taub, R.; Rotenberg, S. A. Biochemistry 1993, 32, 4855-4861.
10. (c) Bennett, C. F.; Chiang, M. Y.; Chan, H.; Shoemaker, J. E.; Mirabelli, C. K. Mol. Pharmacol. 1992, 41, 1023-1033.
11. Shi, F.; Hoekstra, D. J. Controlled Release 2004, 97, 189-209.
12. Manoharan, M. Antisense Nucleic Acid Drug Dev. 2002, 12, 103-128.
13. Zatepsin, T. S.; Stetsenko, D. A.; Gait, M. J.; Oretskaya, T. S. Bioconj. Chem. 2005, 16, 471-489.
14. (a) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
15. (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
16. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.
17. Link, A. J.; Tirrell, D. A. J. Am. Chem. Soc. 2003, 125, 11164-11165.
18. Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687.
19. Bock, V. D.; Speijer, D.; Hiemstra, H.; van Maarseveen, J. H. Org. Biomol. Chem. 2007, 5, 971-975 and references cited herein.
20. Wilkinson, B. L.; Bornaghi, L. F.; Poulsen, S. A.; Houston, T. A. Tetrahedron 2006, 62, 8115-8125.
21. (a) Kuijpers, B. H. M.; Groothuys, S.; Keereweer, A. R.; Quaedflieg, P. J. L. M.; Blaauw, R. H.; van Delft, F. L.; Rutjes, F. P. J. T. Org. Lett. 2004, 6, 3123-3126.
22. (b) Dondoni, A.; Giovannini, P. P.; Massi, A. Org. Lett. 2004, 6, 2929-2932.
23. (c) Lin, H.; Walsh, C. T. J. Am. Chem. Soc. 2004, 126, 13998-14003.
24. (a) Lazrek, H. B.; Engels, J. W.; Pfleiderer, W. Nucleosides Nucleotides 1998, 17, 1851-1856.
25. (b) Park, S. M.; Lee, Y. S.; Kim, B. H. Chem. Commun. 2003, 2912-2913.
26. (c) Gierlich, J. G.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. M.; Carell, T. Org. Lett. 2006, 8, 3639-3642.
27. (d) Burley, G. A.; Gierlich, J.; Mofid, M. R.; Nir, H.; Tal, S.; Eichen, Y.; Carell, T. J. Am. Chem. Soc. 2006, 128, 1398-1399.
28. (e) Seela, F.; Sirivolu, V. R. Chem. Biodiv. 2006, 3, 509-514.
29. (f) Kosiova, I.; Kovackova, S.; Kois, P. Tetrahedron 2007, 63, 312-320.
30. (g) Seela, F.; Sirivolu, V. R. Helv. Chim. Acta 2007, 90, 535-552.
31. (a) Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609-612.
32. (b) Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588-9589.
33. (c) Weller, R. L.; Rajski, S. R. Org. Lett. 2005, 7, 2141-2144.
34. (d) Devaraj, N. K.; Miller, G. P.; Ebina, W.; Kakaradov, B.; Collman, J. P.; Kool, E. T.; Chidsey, C. E. D. J. Am. Chem. Soc. 2005, 127, 8600-8601.
35. (e) Bouillon, C.; Meyer, A.; Vidal, S.; Jochum, A.; Chevolot, Y.; Cloarec, J.-P.; Praly, J.-P.; Vasseur, J.-J.; Morvan, F. J. Org. Chem. 2006, 71, 4700-4702.
36. (f) Meyer, A.; Bouillon, C.; Vidal, S.; Vasseur, J.-J.; Morvan, F. Tetrahedron Lett. 2006, 47, 8867-8871.
37. (g) Kosiova, I.; Kovackova, S.; Kois, P. Tetrahedron 2007, 63, 312-320.
38. Grøtli, M.; Douglas, M.; Eritja, R.; Sproat, B. S. Tetrahedron 1998, 54, 5899-5914.
39. Egli, M.; Minasov, G.; Tereshko, V.; Pallan, P. S.; Teplova, M.; Inamati, G. B.; Lesnik, E. A.; Owens, S. R.; Ross, B. S.; Prakash, T. P.; Manoharan, M. Biochemistry 2005, 44, 9045-9057.
40. Cuenoud, R.; Casset, F.; Hüsken, N. F.; Wolf, R. M.; Almann, K.-H.; Martin, P.; Moser, H. E. Angew. Chem., Int. Ed. 1998, 37, 1288-1291.
41. (a) Yano, J.; Kan, L. S.; Ts'O, P. O. P. Biochim. Biophys. Acta 1980, 629, 178-183.
42. (b) Wagner, E.; Oberhauser, B.; Halzner, A.; Brunar, H.; Issakides, G.; Schaffner, G.; Cotten, M.; Knollmüller, M.; Noe, C. R. Nucl. Acids Res. 1991, 19, 5965-5971.
43. (a) McNamara, J. O.; Andrechek, E. R.; Wang, Y.; Viles, K. D.; Rempel, R. E.; Gilboa, E.; Sullenger, B. A.; Giangrande, P. H. Nat. Biotechnol. 2006, 24, 1005-1015.
44. (b) Chu, T. C.; Twu, K. Y.; Ellington, A. D.; Levy, M. Nucleic Acids Res. 2006, 34, e73.
45. Wada, T.; Mochizuki, A.; Higashiya, S.; Tsuruoka, H.; Kawahar, S.; Ishikawa, M.; Sekine, M. Tetrahedron Lett. 2001, 42, 9215-9219.
46. (a) Poulin-Kerstien, A. T.; Dervan, P. B. J. Am. Chem. Soc. 2003, 125, 15811-15821.
47. (b) Kumar, R.; El-Sagheer, A.; Tumpane, J.; Lincoln, P.; Wilhelmsson, L. M.; Brown, T. J. Am. Chem. Soc. 2007, 129, 6859-6864.