Stereocontrolled synthesis of anthracene β-C-ribosides: Fluorescent probes for photophysical studies of DNA

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1215-1219

  Coleman, Robert S ^a   Mortensen, Mark A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYANTHRACENE; 1 HYDROXYANTHRACENE TRIFLUOROMETHANESULFONATE; 1' ANTHRACEN 1 YL 2' DEOXY C RIBOSIDE; 1' ANTHRACEN 1 YL 3' KETO 2' DEOXY C RIBOSIDE; 1' ANTHRACEN 2 YL 2' DEOXY C RIBOSIDE; 1' ANTHRACEN 2 YL 3' KETO 2' DEOXY C RIBOSIDE; 2 ANTHROL; 2 BROMOANTHRACENE; 2 BROMOANTHRAQUINONE; 2 HYDROXYANTHRACENE TRIFLUOROMETHANESULFONATE; 4 HYDROXY 5 (HYDROXYMETHYL)DIHYDROFURAN; ANTHRACENE DERIVATIVE; FLUORESCENT DYE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DNA PROBE; DNA SYNTHESIS; TECHNIQUE;

EID: 0037415508     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02791-0     Document Type: Article

References (43)

1. Murphy C.J. Photophysical Probes of DNA Sequence-Directed Structure and Dynamics. Adv. Photochem. 26:2001;145-217.
2. Pecourt J.-M.L., Peon J., Kohler B. J. Am. Chem. Soc. 122:2000;9348.
3. Pecourt J.-M.L., Peon J., Kohler B. J. Am. Chem. Soc. 123:2001;10370.
4. Barbara P.F., Jarzeba W. Adv. Chem. Phys. 15:1990;1.
5. Maroncelli M. J. Mol. Liq. 57:1993;1.
6. Coleman R.S., Madaras M.L. J. Org. Chem. 63:1998;5700.
7. Eritja R., Walker P.A., Randall S.K., Goodman M.F., Kaplan B.E. Nucleosides Nucleotides. 6:1987;803.
8. Moog R.S., Davis S.G., Ostrowski S.G., Wilson G.L. Chem. Phys. Lett. 299:1999;265.
9. Horng M.L., Gardecki J.A., Papazyan A., Maroncelli M. J. Phys. Chem. 99:1995;17311.
10. Brauns E.B., Madaras M.L., Coleman R.S., Murphy C.J., Berg M.A. J. Am. Chem. Soc. 121:1999;11644.
11. Brauns E.B., Madaras M.L., Coleman R.S., Murphy C.J., Berg M.A. Phys. Rev. Lett. 88:2002;158101.
12. The 1-anthracenyl 2′-deoxy-C-riboside stereoisomers are described in a patent by Kool (CAN 134:326710), but the coupling of anthracene to the deoxyribose was poorly stereoselective and it relied on the use of stoichiometric cadmium followed by an acid catalyzed anomerization. There are no experimental details in the patent.
13. (a) Morales, R. G. E. J. Phys. Chem. 1982, 86, 2550;
14. (b) Ghoneim, N.; Suppan, P. Spectrochim. Acta 1995, 51A, 1043;
15. (c) Renge, I. J. Photochem. Photobiol. A: Chem. 1992, 69, 135. For time-resolved measurements,
16. see: (d) Zhang, Y.; Berg, M. A. J. Chem. Phys. 2001, 115, 4231; (e) Zhang, Y.; Jiang, J.; Berg, M. A. J. Chem. Phys., submitted for publication.
17. see: (d) Zhang, Y.; Berg, M. A. J. Chem. Phys. 2001, 115, 4231; (e) Zhang, Y.; Jiang, J.; Berg, M. A. J. Chem. Phys., submitted for publication.
18. Berlman I.B. Handbook of Fluorescence Spectra of Aromatic Molecules. 1971;Academic Press, New York.
19. Lambert W.R., Felker P.M., Syage J.A., Zewail A. J. Chem. Phys. 81:1984;2195.
20. Cabri W., Candiani I., DeBernardinis S., Francalanci F., Penco S. J. Org. Chem. 56:1991;5796.
21. Cabri W., Candiani I., Bedeschi A. J. Org. Chem. 55:1990;3654.
22. Cabri W., Candiani I., Bedeschi A. J. Org. Chem. 57:1992;3558.
23. Cabri W., Candiani I. Acc. Chem. Res. 28:1995;2.
24. Cameron M.A., Cush S.B., Hammer R.P. J. Org. Chem. 62:1997;9065.
25. Larson E., Jorgensen P.T., Sofan M.A., Pederson E.B. Synthesis. 1994;1037-1038.
26. Weidhaup K., Kesselaar F.H., Huisman H.O. Tetrahedron. 24:1968;779.
27. Sammes P.G. J. Chem. Soc., Chem. Commun. 1979;33.
28. Sarngadhuran M.G., Seshadri T.R. Indian J. Chem. 4:1966;503.
29. Brisson C., Brassard P. J. Org. Chem. 46:1981;1810.
30. Werntz J.H. J. Am. Chem. Soc. 57:1935;204.
31. Nicoletti T.M., Raston C.L., Sargent M.V. J. Chem. Soc., Perkin Trans. 1. 1990;133.
32. Iwao M., Kuraishi T. Bull. Chem. Soc. Jpn. 60:1987;4051.
33. Sartor G., Bigi F., Tao X., Porta C., Maggi R., Predieri G., Lanfranchi M., Pellinghelli M.A. J. Org. Chem. 60:1995;6588.
34. Morley J.A., Woolsey N.F. J. Org. Chem. 57:1992;6487.
35. Ihmels H. Eur. J. Org. Chem. 1999;1595.
36. Netka J., Crump S.L., Rickborn B. J. Org. Chem. 51:1986;1189.
37. Fitzgerald J.J., Drysdale N.E., Olofson R.A. J. Org. Chem. 57:1992;7122.
38. Doyle M.P., Siegfried B., Dellaria J.F. J. Org. Chem. 42:1977;2426.
39. Klanderman B.H., Criswell T.R. J. Org. Chem. 39:1974;770.
40. von Fierz-David H.E., Blangey L., Streif H. Helv. Chim. Acta. 29:1946;1718.
41. Tuyet J. Tetrahedron. 52:1996;10113.
42. Beletskaya I.P., Cheprakov A.V. Chem. Rev. 100:2000;3009.
43. Evans D.A., Chapman K.T., Carreira E.M. J. Am. Chem. Soc. 110:1988;3560.