"Chemical ligation": A versatile method for nucleoside modification with boron clusters

Chemistry - A European Journal

Volumn 14, Issue 34, 2008, Pages 10675-10682

  Wojtczak, Błazej A ^a   Andrysiak, Agnieszka ^a   Grüner, Bohumír ^b   Lesnikowski, Zbigniew J ^a  

^a INSTITUTE OF MEDICAL BIOLOGY   (Poland)

^b INSTITUTE OF INORGANIC CHEMISTRY   (Czech Republic)

Author keywords

Alkynes; Azides; Chemical ligation; Nucleosides; Thiols

Indexed keywords

ACETYLENE; BEARINGS (STRUCTURAL); BORON; CHEMICAL MODIFICATION; CYCLOADDITION; ETHERS; HYDROCARBONS; NITROGEN COMPOUNDS; NONMETALS; NUCLEOTIDES; PORT TERMINALS; SUGAR (SUCROSE); SUGARS; SYNTHESIS (CHEMICAL);

ALKYNES; AZIDES; CHEMICAL LIGATION; NUCLEOSIDES; THIOLS;

BORON COMPOUNDS;

ALKYNE; AZIDE; BORON DERIVATIVE; NUCLEOSIDE;

ARTICLE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; AZIDES; BORON COMPOUNDS; CYCLIZATION; NUCLEOSIDES;

EID: 56749131185     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801053     Document Type: Article

References (34)

1. Macromolecules Containing Metal and Metal-Like Elements, Vol.3 (Eds.: A. S. Abd-El-Aziz, C. E. Carraher, Jr., C. U. Pittman.Jr., J. E. Sheats, M. Zeldin), John Wiley and Sons, Hoboken, New Jersey, 2004.
2. Z. J. Lesnikowski, Curr. Org. Chem. 2007, 11, 355-381.
3. Z. J. Lesnikowski, A. B. Olejniczak, R. F. Schinazi in Frontiers in Nucleosides and Nucleic Acids (Eds.: R.F. Schinazi, D. C. Liotta), IHL Press. Informed Horizons, LLC. Tucker, GA. 2004, pp. 577-592.
4. Z. J. Lesnikowski, Eur. J. Org. Chem. 2003, 4489-4500.
5. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075:
6. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
7. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128-1136.
8. J. A. Prescher, C. R. Bertozzi, Nat. Chem. Biol. 2005, 1, 13-21.
9. R. Huisgen in 1.3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), Wiley, New York, 1984, pp. 1-176.
10. V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68.
11. D. C. Young, D. V. Howe, M. F. Hawthorne, J. Am. Chem. Soc. 1969, 91, 859-862.
12. Z. Janoušek, S. Heřmánek, J. Plešek, B. Štibr, Collect. Czech. Chem. Commun. 1974, 39, 2363-2373.
13. P. Selucky, J. Plešek, J. Rais, M. Kyrš, L. Kadlecová, J. Radioanal. Nucl. Chem. 1991, 149, 131-140.
14. J. Plešek, B. Grüner, S. Heřmánek, J. Báča, V. Mareček, J. Jänchenová, A. Lhotský, K. Holub, P. Selucký, J. Rais, L. Císař ová, J. Čáslavský, Polyhedron 2002, 21, 975-986.
15. T. Peymann, K. Kück, D. Gabel, Inorg. Chem. 1997, 36, 5138-5139.
16. I. B. Sivaev, Z. A. Starikova, S. Sjöberg, V. I. Bregadze, J. Organomet. Chem. 2002, 649, 1-8.
17. J. Llop, C. Masalles, C. Viñas, R Teixidor, R. Sillanpää, R. Kivekäs, Dalton Trans. 2003, 556-561.
18. A.B. Olejniczak, J. Plesek, Z. J. Leśnikowski, Chem. Eur. J. 2007, 13, 311-318.
19. A. A. Semioshkin, I. B. Sivaev, V. I. Bregadze, Dalton Trans. 2008, 1-16.
20. A. Olejniczak, B. Wojtczak, Z. J. Lesnikowski. Nucl. Nucl. Nucl. Acids 2007, 26, 1611-1613.
21. M. Y. Stogniy, E. N. Abramova, I. A. Lobanova, I. B. Sivaev, V. I. Bragin, P. V. Petrovskii, V. N. Tsupreva, O. V. Sorokina, V. I. Bregadze, Collect. Czech. Chem. Commun. 2007, 72, 1676-1688.
22. A. V. Orlova, N. N. Kondakov, B. G. Kimel, L. O. Kononov, E. G. Kononova, I. B. Sivaev, V. I. Bregadze, Appl. Organomet. Chem. 2007, 21, 98-100.
23. A. A. Semioshkin, S. N. Osipov, J. N. Grebenyuk, E. A. Nizhnik, I. A. Godovikov, G. T. Shchetnikov, V. I. Bregadze, Collect. Czech. Chem. Commun. 2007, 72, 1717-1724.
24. I. B. Sivaev, N. Y. Kulikova, E. A. Nizhnik, M. V. Vichuzhanin, Z. A. Starikova, A. A. Semioshkin, V. I. Bregadze, J. Organomet. Chem. 2008, 693, 519-525.
25. Y. Byun, J. Yan, A. S. Al-Madhoun, J. Johnsamuel, W. Yang, R. F. Barth, S. Eriksson, W. Tjarks, J. Med. Chem. 2005, 48, 1188-1198.
26. J. Johnsamuel, N. Lakhi, A. S. Al-Madhoun, Y. Byun, J. Yan, S. Eriksson, W. Tjarks, Bioorg. Med. Chem. 2004, 12, 4769-4781.
27. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711;
28. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
29. F. G. Rong, A. H. Soloway, S. Ikeda, D. H. Ives, Nucl. Nucl. Nucl. Acids 1995, 14, 1873-1887.
30. Y. Chen, G. L. Barker, J. Org. Chem. 1999, 64, 6870-6873.
31. W. Tjarks, A. K. M. Anisuzzaman, L. Liu, A. H. Soloway, R. F. Barth, D. J. Perkins, D. M. Adams, J. Med. Chem. 1992, 35, 1628-1633.
32. J. Plešek, T. Jelinek, F. Mares, S. Hermanek, Collect. Czech. Chem. Commun. 1993, 58, 1534-1547.
33. J. Plesek, S. Hermanek, A. Franken, I. Cisarova, C. Nachtigal, Collect. Czech. Chem. Commun. 1997, 62, 47-56.
34. J. Plesek, B. Gruner, J. Machacek, I. Cisarova, J. Caslavsky, J. Organomet. Chem. 2007, 692, 4801-4804.