The first postsynthetic 5′-5′ intercalators in triplex DNA - Solid-phase postsynthetic Sonogashira reaction and homocouplings on arylacetylenes

Helvetica Chimica Acta

Volumn 92, Issue 4, 2009, Pages 716-730

  Bomholt, Niels ^a   Filichev, Vyacheslav V ^b   Pedersen, Erik B ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b MASSEY UNIVERSITY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLACETYLENES; DIETHYNYLBENZENE; DNA SYNTHESIS; HOMOCOUPLING; INTERCALATORS; MOLECULAR MODELLING; NEW ZEALAND; OLIGODEOXYNUCLEOTIDES; PHOSPHORAMIDITE; POLYPYRIMIDINE; POSTSYNTHESIS; POSTSYNTHETIC MODIFICATION; REPRODUCIBILITY; SOLID-PHASE; SONOGASHIRA COUPLING; SONOGASHIRA REACTIONS; THERMAL STABILITY; TRIPLEX DNA;

GENES; NUCLEIC ACIDS; OLIGONUCLEOTIDES; SYNTHESIS (CHEMICAL);

DNA;

1,3 DIETHYNYLBENZENE; 2 (3 IODOBENZYLOXY)ETHYL PHOSPHATE; ACETYLENE DERIVATIVE; BENZENE DERIVATIVE; CPG OLIGODEOXYNUCLEOTIDE; DNA; INTERCALATING AGENT; OLIGONUCLEOTIDE; PHOSPHATE; TRIPLEX FORMING OLIGONUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; DNA SYNTHESIS; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS; SONOGASHIRA REACTION; THERMOSTABILITY;

EID: 65749105567     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200800397     Document Type: Article

References (26)

1. R. V. Guntaka, B. R. Varma, K. T. Weber, Int. J. Biochem. Cell. Biol. 2003, 35, 22.
2. D. Praseuth, A. L. Guieysse, C. Hélène, Biochim. Biophys. Acta 1999, 1489, 181.
3. M. Faria, C. Giovannangeli, J. Gene Med. 2001, 3, 299.
4. L. E. Xodo, G. Manzini, F. Quadrifoglio, G. A. van der Marcel, J. H. van Boom, Nucleic Acids Res. 1991, 19, 5625.
5. P. L. James, T. Brown, K. R. Fox, Nucleic Acids Res. 2003, 31, 5598.
6. V. V. Filichev, E. B. Pedersen, J. Am. Chem. Soc. 2005, 127, 14849.
7. M. Paramavisam, C. Susanna, V. V. Filichev, N. Bomholt, E. B. Pedersen, L. E. Xodo, Nucleic Acid Res. 2008, 36, 3494.
8. S. Buchini, C. J. Leumann, Curr. Opin. Chem. Biol. 2003, 7, 717.
9. S. Hoshika, Y. Ueno, A. Matsuda, Bioconjugate Chem. 2003, 14, 607.
10. H. C. Jessen, E. B. Pedersen, Helv. Chim. Acta 2004, 87, 2465.
11. V. V. Filichev,M. C. Nielsen, N. Bomholt, C. H. Jessen, E. B. Pedersen, Angew. Chem., Int. Ed. 2006, 45, 5311.
12. I. Géci, V. V. Filichev, E. B. Pedersen, Bioconjugate Chem. 2006, 17, 950.
13. S. I. Khan, M.W. Grinstaff, J. Am. Chem. Soc. 1999, 121, 4704.
14. A. E. Beilstein, M.W. Grinstaff, Chem. Commun. 2000, 509.
15. M. Rist, N. Amann, H.-A. Wagenknecht, Eur. J. Org. Chem. 2003, 2498.
16. P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem., Int. Ed. 2000, 39, 2632.
17. A. Elangovan, Y.-H. Wang, T.-I. Ho, Org. Lett. 2003, 5, 1841.
18. H. G. Viehe, 'Chemistry of Acetylenes', Marcel Dekker Inc., New York, 1969, p. 599.
19. N. Minakawa, Y. Ono, A. Matsuda, J. Am. Chem. Soc. 2003, 125, 11545.
20. T. Matsuda, S. Kadowaki, M. Murakami, Chem. Commun. 2007, 2627.
21. J.-L. Mergny, L. Lacroix, Oligonucleotides 2003, 13, 515.
22. C. Giovannangeli, L. Perrouault, C. Escudé, N. Thuong, C. Hélène, Biochemistry 1996, 35, 10539.
23. C. Giovannangeli, L. Perrouault, C. Escudé, S. Gryaznov, C. Hélène, J. Mol. Biol. 1996, 261, 386.
24. A. Błaszczyk, M. Chadim, C. von Ḧnisch, M. Mayor, Eur. J. Org. Chem. 2006, 3809.
25. M. Tanimoto, K. Kuchitsu, Y. Morino, Bull. Chem. Soc. Jpn. 1971, 44, 386.
26. G. A. Williams, J. N. Macdonald, J. Mol. Struct. 1994, 320, 217.