An efficient method for the construction of functionalized dna bearing amino acid groups through cross-coupling reactions of nucleoside triphosphates followed by primer extension or PCR

Chemistry - A European Journal

Volumn 13, Issue 21, 2007, Pages 6196-6203

  Čapek, Petr ^a   Cahová, Hana ^a   Pohl, Radek ^a   Hocek, Michal ^a   Gloeckner, Christian ^b   Marx, Andreas ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Cross coupling; DNA; Nucleosides; Nucleotides; Polymerase chain reaction

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; DNA SEQUENCES; ENZYME KINETICS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CROSS-COUPLING; DNA DUPLEXES; POLYMERASE CHAIN REACTION;

COMPLEXATION;

AMINO ACID; DNA; DNA DIRECTED DNA POLYMERASE; NUCLEOSIDE; NUCLEOTIDE; PRIMER DNA;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; GENETICS; METABOLISM; METHODOLOGY; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; POLYMERASE CHAIN REACTION;

AMINO ACIDS; BASE SEQUENCE; CIRCULAR DICHROISM; DNA; DNA PRIMERS; DNA-DIRECTED DNA POLYMERASE; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NUCLEOSIDES; NUCLEOTIDES; POLYMERASE CHAIN REACTION;

EID: 34547208319     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700220     Document Type: Article

References (40)

1. a) R. R. Breaker, Curr. Opin. Chem. Biol. 1997, 1, 26-31;
2. b) M. Famulok, G. Mayer, M. Blind, Acc. Chem. Res. 2000, 33, 591-599;
3. c) M. Famulok, Curr. Opin. Mol. Ther. 2005, 7, 137-143.
4. a) H. Hashimoto, M. G. Nelson, C. Schwitzer, J. Am. Chem. Soc. 1993, 115, 7128-7134;
5. b) H. Rosemeyer, N. Ramzaeva, E.-M. Becker, E. Feiling, F. Seela, Bioconjugate Chem. 2002, 13, 1274-1285;
6. c) J. A. Brazier, T. Shibata, J. Townsley, B. F. Taylor, E. Frary, N. H. Williams, D. M. Williams, Nucleic Acids Res. 2005, 33, 13621371.
7. a) J. Gierlich, G. A. Burley, P. M. E. Gramlich, D. M. Hammond, T. Carell, Org. Lett. 2006, 8, 3639-3642;
8. b) G. Burley, J. Gierlich, M. R. Mofid, H. Nir, S. Tal, Y. Eichen, T. Carell, J. Am. Chem. Soc. 2006, 128, 1398-1399.
9. a) K. Sakthivel, C. F. Barbas, III, Angew. Chem. Int. Ed. 1998, 37, 2872-2875;
10. b) H. Sawai, A. Ozaki-Nakamura, M. Mine, H. Ozaki, Bioconjugate Chem. 2002, 13, 309-316;
11. c) M. M. Masud, A. OzakiNakamura, M. Kuwahara, H. Ozaki, H. Sawai, ChemBioChem 2003, 4, 584-588;
12. d) M. Kuwahara, J. Nagashima, M. Hasegawa, T. Tamura, R. Kitagata, K. Hanawa, S. Hososhima, T. Kasamatsu, H. Ozaki, H. Sawai, Nucleic Acids Res. 2006, 34, 5383-5394;
13. e) T. Gourlain, A. Sidorov, N. Mignet, S. J. Thorpe, S. E. Lee, J. A. Grasby, D. M. Williams, Nucleic Acids Res. 2001, 29, 1898-1905.
14. a) O. Thum, S. Jäger, M. Famulok, Angew. Chem. Int. Ed. 2001, 40, 3990-3993;
15. b) S. Jäger, M. Famulok, Angew. Chem. Int. Ed. 2004, 43, 3337-3340;
16. c) S. Jäger, G. Rasched, H. Kornreich-Leshem, M. Engeser, O. Thum, M. Famulok, J. Am. Chem. Soc. 2005, 127, 15071-15082.
17. H. Sawai, A. N. Ozaki, F. Satoh, T. Ohbayashi, M. M. Masud, H. Ozaki, Chem. Commun. 2001, 2601-2605.
18. A. Shoji, T. Hasegawa, M. Kuwahara, H. Ozaki, H. Sawai, Bioorg. Med. Chem. Lett. 2007, 17, 776-779.
19. a) D. A. Di Giusto, W. A. Wlassoff, S. Geisebrecht, J. J. Gooding, G. C. King, J. Am. Chem. Soc. 2004, 126, 4120-4121;
20. b) D. A. Di G-iusto, W. A. Wlassoff, S. Geisebrecht, J. J. Gooding, G. C. King, Angew. Chem. Int. Ed. 2004, 43, 2809-2812;
21. c) W. A. Wlassoff, G. C. King, Nucleic Acids Res. 2002, 30, e58;
22. d) S. S. W. Yeung, T. M. H. Lee, I-M. Hsing, J. Am. Chem. Soc. 2006, 128, 13374-13375.
23. M. Kuwahara, K. Hanawa, K. Ohsawa, R. Kitagata, H. Ozaki, H. Sawai, Bioorg. Med. Chem. 2006, 14, 2518-2526.
24. M. Matsui, Y. Nishiyama, S. Ueji, Y. Ebara, Bioorg. Med. Chem. Lett. 2007, 17, 456-460.
25. L. H. Thoresen, G.-S. Jiao, W. C. Haaland, M. L. Metzker, K. Burgess, Chem. Eur. J. 2003, 9, 4603-4610.
26. P. Čapek, R. Pohl, M. Hocek, Org. Biomol. Chem. 2006, 4, 2278-2284.
27. a) E. C. Western, J. R. Daft, E. M. Johnson, P. M. Gannett, K. H. Shaughnessy, J. Org. Chem. 2003, 68, 6767-6774;
28. b) E. C. Western, K. H. Shaughnessy, J. Org. Chem. 2005, 70, 6378-6388;
29. c) recent comprehensive review: K. H. Shaughnessy, Eur. J. Org. Chem. 2006, 1827-1835.
30. A. Collier, G. Wagner, Org. Biomol. Chem. 2006, 4, 4526-4532.
31. Reviews: a) M. Hocek, Eur. J. Org. Chem. 2003, 245-254;
32. b) L. A. Agrofoglio, I. Gillaizeau, Y. Saito, Chem. Rev. 2003, 103, 1875-1916;
33. c) M. K. Lakshman, J. Organomet. Chem. 2002, 653, 234-251.
34. P. Čapek, M. Hocek, Synlett 2005, 3005-3007.
35. P. Čapek, M. Vrábel, Z. Hasník, R. Pohl, M. Hocek, Synthesis 2006, 3515-3526.
36. J. M. Clark, Nucleic Acids Res. 1988, 16, 9677.
37. M. Ikehara, M. Kaneko, Chem. Pharm. Bull. 1970, 18, 2441-2446.
38. L. S. Gordeeva, Yu. L. Kaminskii, N. L. Rumyantseva, N. A. Patokina, N. A. Korsakova, L. F. Chernysheva, V. K. Dedova, V. L. Efimova, A. G. Neopikhanova, Khim. Prir. Soedin. 1984, 6, 771-776.
39. F. Seela, M. Zulauf, H. Rosemeyer, H. Reuter, J. Chem. Soc. Perkin Trans. 2 1996, 2373-2376.
40. T. Kovacs, L. Ötvös, Tetrahedron Lett. 1988, 29, 4525-4528.