Tritylisation of pyrene, perylene and coronene: A new family of switchable fluorescent labels

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4943-4948

  Shchepinov, Mikhail S ^a   Korshun, Vladimir A ^b   Egeland, Ryan D ^a   Southern, Edwin M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

Author keywords

Fluorescence; Friedel Crafts reactions; Grignard reactions; Nucleic acids; Polycyclic aromatic compounds

Indexed keywords

PERYLENE; POLYCYCLIC AROMATIC COMPOUND; PYRENE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DNA MICROARRAY; FLUORESCENCE; PH; REACTION ANALYSIS;

EID: 0034686347     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00737-1     Document Type: Article

References (22)

1. Smith, L. M.; Sanders, J. Z.; Kaiser, R. J.; Hughes, P.; Dodd, C.; Connell, C. R.; Heiner, C.; Kent, S. B. H.; Hood, L. E. Nature 1986, 321, 674-679.
2. (a) Cardullo, R. A.; Agrawal, S.; Flores, C.; Zamecnic, P. C.; Wolf, D. E., et. al. Proc. Natl. Acad. Sci. USA 1988, 85, 8790-8794.
3. (b) Tyagi, S.; Kramer, F. R. Nat. Biotechnol. 1996, 14, 303-308.
4. (c) Lewis, F. D.; Zhang, Y.; Letsinger, R. L. J. Am. Chem. Soc. 1997, 119, 5451-5452.
5. (d) Masuko, M.; Ohuchi, S.; Sode, K.; Ohtani, H.; Shimadzu, A. Nucleic Acids Res. 2000, 28, e35.
6. (e) Mao, C. D.; Sun, W. Q.; Shen, Z. Y.; Seeman, N. C. Nature 1999, 397, 144-146.
7. (f) Dobrikov, M. I.; Gainutdinov, T. I.; Vlassov, V. V. Nucleosides Nucleotides 1999, 18, 1517-1518.
8. Reines, S. A.; Cantor, C. R. Nucleic Acids Res. 1974, 1, 767-786.
9. Johansson, L. B.-A.; Molotkovsky, J. G.; Bergelson, L. D. J. Am. Chem. Soc. 1987, 109, 7374-7381.
10. Rohr, U.; Schlichting, P.; Bohm, A.; Gross, M.; Meerholz, K.; Brauchle, C.; Mullen, K. Angew. Chem., Int. Ed. 1998, 37, 1434-1437.
11. Zieger, H. E. J. Org. Chem. 1966, 31, 2977-2981.
12. (a) Gildea, B. D.; Coull, J. M.; Koster, H. Tetrahedron Lett. 1990, 31, 7095-7098.
13. (b) Shchepinov, M. S.; Chalk, R.; Southern, E. M. Nucleic Acids Symp. Ser. 1999, 42, 107-108.
14. (c) Shchepinov, M. S.; Chalk, R.; Southern, E. M. Tetrahedron 2000, 56, 2715-2726.
15. 2).
16. Fourrey, J. L.; Varenne, J.; Blonski, C.; Dousset, P.; Shire, D. Tetrahedron Lett. 1987, 28, 5157-5160.
17. Smith, M.; Rammler, D. H.; Goldberg, I. H.; Khorana, H. G. J. Am. Chem. Soc. 1961, 84, 430-440.
18. 2) was as follows: DMTrOH <7<9~MMTrOH<8
19. Klinger, K. W.; Landes, G.; Dackowski, W.; Leverone, B.; Lopez, L.; Locke, P.; Ward, D.; Ried, T. Cytogenet. Cell Genet. 1991, 58, 2149.
20. Schena, M.; Shalon, D.; Davis, R. W.; Brown, P. O. Science 1995, 270, 467-470.
21. Fisher, E. F.; Caruthers, M. H. Nucleic Acids Res. 1983, 11, 1589-1599.
22. Lee, L. G.; Spurgeon, S. L.; Heiner, C. R.; Benson, S. C.; Rosenblum, B. B.; Menchen, S. M.; Graham, R. J.; Constantinescu, A.; Upadhya, K. G.; Cassel, J. M. Nucleic Acids Res. 1997, 25, 2816-2822.