TTF-modified DNA

Chemistry - A European Journal

Volumn 14, Issue 19, 2008, Pages 5732-5736

  Bouquin, Nicolas ^a   Malinovskii, Vladimir L ^a   Guégano, Xavier ^a   Liu, Shi Xia ^a   Decurtins, Silvio ^a   Häner, Robert ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

DNA; Fluorescence; Oligonucleotides; Tetrathiafulvalene

Indexed keywords

DNA; FLOW INTERACTIONS; GENES; HYDROPHOBICITY; ORGANIC ACIDS; PROCESS ENGINEERING; PYROLYSIS;

COOPERATIVITY; DENATURATION PROCESS; DNA DUPLEXES; DUPLEX STABILITY; FLUORESCENCE; HYDROPHOBIC INTERACTIONS; MELTING PROCESSES; MODIFIED DNA; NUCLEOBASES; OLIGONUCLEOTIDES; STACKING INTERACTIONS; TETRATHIAFULVALENE;

NUCLEIC ACIDS;

DNA; HETEROCYCLIC COMPOUND; OLIGONUCLEOTIDE; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDOUS ACID; TETRATHIAFULVALENE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; NUCLEOTIDE SEQUENCE; SPECTROFLUOROMETRY; SYNTHESIS; TEMPERATURE;

BASE SEQUENCE; CIRCULAR DICHROISM; DNA; HETEROCYCLIC COMPOUNDS; OLIGONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; SPECTROMETRY, FLUORESCENCE; TEMPERATURE;

EID: 53849142132     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800505     Document Type: Article

References (67)

1. F. Wudl, G. M. Smith, E. J. Hufnagel, J. Chem. Soc. Chem. Commun. 1970, 1453-1454.
2. J. Yamada, T. Sugimoto, TTF Chemistry. Fundamentals and Applications of Tetrathiafitlvalene, Springer, Berlin, 2004.
3. J. L. Segura, N. Martin, Angew. Chem. 2001, 113, 1416-1455;
4. Angew. Chem. Int. Ed. 2001, 40, 1372-1409.
5. See also the special issue on molecular conductors in Chem. Rev. 2004, 104, 4887-5056.
6. M. B. Nielsen, C. Lomholt, J. Becher, Chem. Soc. Rev. 2000, 29, 153-164.
7. C. Goze, C. Leiggener, S. X. Liu, L. Sanguinet, E. Levillain, A. Hauser, S. Decurtins, ChemPhysChem 2007, 8, 1504-1512.
8. F. Dumur, N. Gautier, N. Gallego-Planas, Y. Sahin, E. Levillain, N. Mercier, P. Hudhomme, M. Masino, A. Girlando, V. Lloveras, J. Vidal-Gancedo, J. Veciana, C. Rovira, J. Org. Chem. 2004, 69, 2164-2177.
9. M. R. Bryce, J. Mater. Chem. 2000, 10, 589-598.
10. C. Y. Jia, S. X. Liu, C. Tanner. C. Leiggener, L. Sanguinet. E. Levillain, S. Leutwyler, A. Hauser, S. Decurtins, Chem. Commun. 2006, 1878-1880.
11. G. Ho, J. R. Heath, M. Kondratenko, D. F. Perepichka, K. Arseneault, M. Pezolet, M. R. Bryce, Chem. Eur. J. 2005, 11, 2914-2922.
12. E. Tsiperman, J. Y. Becker, V. Khodorkovsky, A. Shames, L. Shapiro, Angew. Chem. 2005, 117, 4083-4086;
13. Angew. Chem. Int. Ed. 2005, 44, 4015-4018.
14. J. Wu, S. X. Liu, A. Neels, F. Le Derf, M. Salle, S. Decurtins, Tetrahedron 2007, 63, 11282-11286.
15. N. Martin, L. Sanchez, M. A. Herranz, B. Illescas, D. M. Guldi, Acc. Chem. Res. 2007, 40, 1015-1024.
16. J. Puigmarti-Luis, V. Laukhin, A. P. del Pino, J. Vidal-Gancedo, C. Rovira, E. Laukhina, D. B. Amabilino, Angew. Chem. 2007, 119, 242-245;
17. Angew. Chem. Int. Ed. 2007, 46, 238-241.
18. C. Wang, D. Q. Zhang, D. B. Zhu, J. Am. Chem. Soc. 2005, 127, 16372-16373.
19. N. C. Seeman, Mol. Biotechnol. 2007, 37, 246-257.
20. U. Feldkamp, C. M. Niemeyer, Angew. Chem. 2006, 118, 1888-1910;
21. Angew. Chem. Int. Ed. 2006, 45, 1856-1876.
22. F. D. Lewis, E. L. Burch, J. Photochem. Photobiol. A 1996, 96, 19-23.
23. S. M. Langenegger, R. Häner, Bioorg. Med. Chem. Lett. 2006, 16, 5062-5065.
24. S. M. Langenegger, R. Häner, Helv. Chim. Acta 2002, 85, 3414-3421.
25. M. Nakamura, Y. Ohtoshi, K. Yamana, Chem. Commun. 2005, 5163-5165.
26. F. Samain, V. L. Malinovskii, S. M. Langenegger, R. Häner, Bioorg. Med. Chem. 2008, 16, 27-33.
27. S. M. Langenegger, R. Häner, Chem. Commun. 2004, 2792-2793.
28. U. B. Christensen, E. B. Pedersen, Helv. Chim. Acta 2003, 86, 2090-2097.
29. I. Trkulja, R. Häner, Bioconjugate Chem. 2007, 18, 289-292.
30. I. Trkulja, R. Häner, J. Am. Chem. Soc. 2007, 129, 7982-7989.
31. A. Okamoto, T. Ichiba, I. Saito, J. Am. Chem. Soc. 2004, 126, 8364-8365.
32. A. D. Malakhov, M. V. Skorobogatyi, I. A. Prokhorenko, S. V. Gontarev, D. T. Kozhich, D. A. Stetsenko, I. A. Stepanova, Z. O. Shenkarev, Y. A. Berlin, V. A. Korshun, Eur. J. Org. Chem. 2004, 1298-1307.
33. Y. Zheng, H. Long, G. C. Schatz, F. D. Lewis, Chem. Commun. 2005, 4795-4797.
34. N. Rahe, C. Rinn, T. Carell, Chem. Commun. 2003, 2119-2121.
35. C. Wagner, H. A. Wagenknecht, Org. Lett. 2006, 8, 4191-4194.
36. S. Bevers, S. Schutte, L. W. McLaughlin, J. Am. Chem. Soc. 2000, 122, 5905-5915.
37. W. Wang, W. Wan, H. H. Zhou, S. Q. Niu, A. D. Q. Li, J. Am. Chem. Soc. 2003, 125, 5248-5249.
38. U. B. Christensen, E. B. Pedersen, Nucl. Acids Res. 2002, 30, 4918-4925.
39. S. M. Langenegger, G. Bianké, R. Tona, R. Häner, Chimia 2005, 59, 794-797.
40. H. Kashida, H. Asanuma, M. Komiyama, Angew. Chem. 2004, 116, 6684-6687;
41. Angew. Chem. Int. Ed. 2004, 43, 6522-6525.
42. W. Wang, A. D. Q. Li, Bioconjugate Chem. 2007, 18, 1036-1052.
43. F. D. Lewis, X. Liu, Y. Wu, S. E. Miller, M. R. Wasielewski, R. L. Letsinger, R. Sanishvili, A. Joachimiak, V. Tereshko, M. Egli, J. Am. Chem. Soc. 1999, 121, 9905-9906.
44. A. Stutz, S. M. Langenegger, R. Häner, Helv. Chim. Acta 2003, 86, 3156-3163.
45. G. Bianké, R. Häner, Nucleosides Nucleotides Nucleic Acids 2007, 26, 949-952.
46. G. Bianké, R. Häner, ChemBioChem 2004, 5, 1063-1068.
47. F. D. Lewis, L. G. Zhang, R. F. Kelley, D. McCamant, M. R. Wasielewski, Tetrahedron 2007, 63, 3457-3464.
48. M. Nakamura, M. Ueda, S. Watanabe, S. Kumamoto, K. Yamana, Tetrahedron Lett. 2007, 48, 6159-6162.
49. V. Looser, S. M. Langenegger, R. Häner, J. S. Hartig, Chem. Commun. 2007, 4357-4359.
50. K. Yamana, A. Yoshikawa, H. Nakano, Tetrahedron Lett. 1996, 37, 637-640.
51. H. Asanuma, T. Ito, T. Yoshida, X. G. Liang, M. Komiyama, Angew. Chem. 1999, 111, 2547-2549;
52. Angew. Chem. Int. Ed. 1999, 38, 2393-2395.
53. F. D. Lewis, Y. S. Wu, X. Y. Liu, J. Am. Chem. Soc. 2002, 124, 12165-12173.
54. V. L. Malinovskii, F. Samain, R. Häner, Angew. Chem. 2007, 119, 4548-4551;
55. Angew. Chem. Int. Ed. 2007, 46, 4464-4467.
56. H. Kashida, M. Tanaka, S. Baba, T. Sakamoto, G. Kawai, H. Asanuma, M. Komiyama, Chem. Eur. J. 2006, 12, 777-784.
57. N. Bouquin, V. L. Malinovskii, R. Häner, Chem. Commun. 2008, 1974-1976.
58. See. for example: a) S. J. Pace, P. F. Man, A. P. Patil, K. F. Tan, CNT-based sensors: devices, processes and uses thereof, PCT Int. Appl. (2007), WO 2007089550;
59. b) G.-U. Flechsig, T. Reske, Selective Labeling of single-stranded regions of nucleic acid hybrids in the electrochemical detection of hybrids, Ger. (2007). DE 102005039726.
60. O. Neilands, V. Liepinsh, B. Turovska, Org. Lett. 1999, 1, 2065-2067.
61. S. Leroy-Lhez, J. Baffreau, L. Perrin, E. Levillain, M. Allain, M. J. Blesa, P. Hudhomme, J. Org. Chem. 2005, 70, 6313-6320.
62. S. L. Beaucage, M. H. Caruthers, Tetrahedron Lett. 1981, 22, 1859-1862.
63. High coupling yields were obtained during oligonucleotide synthesis. Some fragmentation of the oligomers at the site of the tetrathiafulvalene building block during ammonia deprotection was observed, however.
64. F. M. Winnik, Chem. Rev. 1993, 93, 587-614.
65. N. Berova, L. Di Bari, G. Pescitelli, Chem. Prod. Chem. Soc. Rev. 2007, 36, 914-931.
66. C. Loosli, C. Y. Jia, S. X. Liu, M. Haas, M. Dias, E. Levillain, A. Neels, G. Labat, A. Hauser, S. Decurtins, J. Org. Chem. 2005, 70, 4988-4992.
67. S. Delahaye, C. Loosli, S. X. Liu, S. Decurtins, G. Labat, A. Neels, A. Loosli, T. R. Ward, A. Hauser, Adv. Funct. Mater. 2006, 16, 286-295.