Synthesis of oligonucleotides carrying 5′-5′ linkages using copper-catalyzed cycloaddition reactions

Chemistry and Biodiversity

Volumn 4, Issue 12, 2007, Pages 2798-2809

  Alvira, Margarita ^a   Eritja, Ramon ^a  

^a BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AZIDE; COPPER DERIVATIVE; OLIGONUCLEOTIDE; PHOSPHORAMIDON;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CYCLOADDITION; GEL ELECTROPHORESIS; GENE STRUCTURE; GENETIC LINKAGE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEOTIDE SEQUENCE; SOLID PHASE SYNTHESIS; VELOCITY;

CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; COPPER; CROSS-LINKING REAGENTS; CYCLIZATION; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES;

EID: 38049047661     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200790229     Document Type: Article

References (29)

1. V. Marchán, S. Ortega, D. Pulido, E. Pedroso, A. Grandas, Nucleic Acids Res. 2006, 34, e24.
2. D. Graham, A. Enright, Curr. Org. Chem. 2006, 3, 9.
3. H. A. Latham-Timmons, A. Wolter, J. S. Roach, R. Giare, M. Leuck, Nucleosides, Nucleotides Nucleic Acids 2003, 22, 1495.
4. M. Proupin-Perez, R. Cosstick, L. M. Liz-Marzan, V. Salgueiriño-Maceira, M. Brust, Nucleosides Nucleotides Nucleic Acids 2005, 24, 1075.
5. R. Huisgen, Angew. Chem., Int. Ed. 1963, 2, 565.
6. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2001, 40, 2004.
7. C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057.
8. S. Punna, J. Kuzelka, Q. Wang, M. G. Finn, Angew. Chem., Int. Ed. 2005, 44, 2215.
9. J. L. Brennan, N. S. Hatzakis, T. R. Tshikhudo, N. Dirvianskyte, V. Razumas, S. Patkar, J. Vind, A. Svendsen, R. J. M. Nolte, A. E. Rowan, M. Brust, Bioconjugate Chem. 2006, 17, 1373.
10. R. L. Weller, S. R. Rajski, Org. Lett. 2005, 7, 2141.
11. N. K. Devaraj, G. P. Miller, W. Ebina, B. Kakaradov, J. P. Collman, E. T. Kool, C. E. D. Chidsey, J. Am. Chem. Soc. 2005, 127, 8600.
12. M. W. Kanan, M. M. Rozenman, K. Sakurai, T. M. Snyder, D. R. Liu, Nature 2004, 431, 545.
13. T. S. Seo, Z. Li, H. Ruparel, J. Ju, J. Org. Chem. 2003, 68, 609.
14. T. S. Seo, X. Bai, H. Ruparel, Z. Li, N. J. Turro, J. Ju, Proc. Natl. Acad. Sci U.S.A. 2004, 101, 5488.
15. C. Bouillon, A. Meyer, S. Vidal, A. Jochhum, Y. Chevolot, J. P. Cloarec, J. P. Praly, J. J. Vasseur, F. Morvan, J. Org. Chem. 2006, 71, 4700.
16. A. Meyer, C. Bouillon, S. Vidal, J. J. Vasseur, F. Morvan, Tetrahedron Lett. 2006, 47, 8867.
17. F. Seela, V. R. Sirivolu, Chem. Biodiv. 2006, 3, 509.
18. R. Kumar, A. El-Sagheer, J. Tampane, P. Lincoln, L. M. Wihelmsson, T. Brown, J. Am. Chem. Soc. 2007, 129, 6859.
19. J. H. van den Sande, N. B. Ramsing, M. W. Germann, W. Elhorst, B. W. Kalisch, E. V. Kitzing, R. T. Pon, R. C. Clegg, T. M. Jovin, Science 1988, 241, 551.
20. E. R. Kandimalla, S. Agrawal, G. Venkataraman, V. Sasisekharan, J. Am. Chem. Soc. 1995, 117, 6416.
21. E. R. Kandimalla, S. Agrawal, Biochemistry 1996, 35, 15332.
22. A. Aviñó, M. Frieden, J. C. Morales, B. G. de la Torre, R. Güimil García, F. Azorín, J. L. Gelpí, M. Orozco, C. González, R. Eritja, Nucleic Acids Res. 2002, 30, 2609.
23. M. Koeh, R. Breinbauer, Angew. Chem., Int. Ed. 2004, 43, 3106.
24. J. Liu, Q. R. Fan, M. Sodeoka, W. S. Lane, G. L. Verdine, Chem. Biol. 1994, 1, 47.
25. C. Fàbrega, R. Güimil-García, A. R. Díaz, R. Eritja, Biol. Chem. 1998, 379, 527.
26. M. Frieden, A. Aviñó, R. Eritja, Nucleosides Nucleotides Nucleic Acids 2003, 22, 193.
27. G. P. Miller, E. T. Kool, Org. Lett. 2002, 4, 3599.
28. B. Y. Lee, S. R. Park, H. B. Jeon, K. S. Kim, Tetrahedron Lett. 2006, 47, 5105.
29. Z. Li, T. S. Seo, J. Ju, Tetrahedron Lett. 2004, 45, 3143.