Photoregulation of the formation and dissociation of a DNA duplex by using the cis-trans isomerization of azobenzene

Angewandte Chemie - International Edition

Volumn 38, Issue 16, 1999, Pages 2393-2395

  Asanuma, Hiroyuki ^a   Ito, Takanori ^a   Yoshida, Takayuki ^a   Liang, Xingguo ^a   Komiyama, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Azo compounds; DNA structures; Isomerizations; Nucleotides; Photochemistry

Indexed keywords

AZO COMPOUND; DOUBLE STRANDED DNA;

ARTICLE; CHEMICAL MODIFICATION; CHIRALITY; COLONY FORMING UNIT; DISSOCIATION CONSTANT; DNA STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; PHOTOCHEMISTRY;

EID: 0033549733     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2393::AID-ANIE2393>3.0.CO;2-7     Document Type: Article

References (24)

1. a) A. Kume, M. Fujii, M. Sekine, T. Hata, J. Org. Chem. 1984, 49, 2139-2143;
2. b) C. J. Murphy, M. R. Arkin, Y. Jenkins, N. D. Ghatlia, S. H. Bossmann, N. J. Turro, J. K. Barton, Science 1993, 262, 1025-1029;
3. c) K. Yamana, R. Aota, H. Nakano, Tetrahedron Lett. 1995, 36, 8427-8430;
4. d) C. Giovannangeli, L. Perrouault, C. Escudé, N. Thuong, C. Hélène, Biochemistry 1996, 35, 10539-10548;
5. e) S. A. Boutonne, D. Brault, M. Takasugi, O. Delgado, C. Hélène, J. Am. Chem. Soc. 1996, 118, 9469-9476;
6. f) R. L. Letsinger, T. Wu, J. Am. Chem. Soc. 1994, 116, 811-812;
7. g) E. T. Kool, Chem. Rev. 1997, 97, 1473-1487;
8. h) M. S. Shchepinov, I. A. Udalova, A. J. Bridgman, E. M. Southern, Nucleic Acids Res. 1997, 25, 4447-4454;
9. i) L. Deng, O. D. Schärer, G. L. Verdine, J. Am. Chem. Soc. 1997, 119, 7856-7866;
10. j) T. E. Lehmann, W. A. Greenberg, D. A. Liberles, C. K. Wada, P. B. Dervan, Helv. Chim. Acta 1997, 80, 2002-2022;
11. k) P. Zhang, W. T. Johnson, D. Klewer, N. Paul, G. Hoops, V. J. Davisson, D. E. Bergstrom, Nucleic Acids Res. 1998, 26, 2208-2215;
12. l) K. Berlin, R. K. Jain, M. D. Simon, C. Richert, J. Org. Chem. 1998, 63, 1527-1535;
13. m) D. J. Earnshaw, M. J. Gait, Biopolymers 1998, 48, 39-55;
14. n) G. D. Glick, Biopolymers 1998, 48, 83-96, and references therein.
15. Control of the replication and transcription of DNA might be possible, since both processes involve the dissociation of a DNA duplex to single strands prior to the chemical reactions.
16. H. Asanuma, T. Ito, M. Komiyama, Tetrahedron Lett. 1998, 39, 9015-9018.
17. The introduction of azobenzene to the main chain of oligonucleotide has been reported: K. Yamana, A. Yoshikawa, N. Nakao, Tetrahedron Lett. 1996, 37, 637-640; K. Yamana, A. Yoshikawa, R. Noda, H. Nakao, Nucleosides Nucleotides 1998, 17, 233-242.
18. The introduction of azobenzene to the main chain of oligonucleotide has been reported: K. Yamana, A. Yoshikawa, N. Nakao, Tetrahedron Lett. 1996, 37, 637-640; K. Yamana, A. Yoshikawa, R. Noda, H. Nakao, Nucleosides Nucleotides 1998, 17, 233-242.
19. 2O gradient from 5/95 to 50/50 at 25 min.
20. The pure trans isomer isolated by HPLC was partially (about 10%) converted into the cis isomer by ambient light.
21. m value of the cis isomer, UV light was irradiated in the middle of the measurement to minimize the effect of the thermal isomerization to the trans form. By this treatment, the fraction of the cis isomer was kept almost constant at 70% throughout the measurement, as confirmed by HPLC and UV/Vis spectroscopy.
22. 1 at pH 7.1 (without NaCl)). Here the modified oligonucleotide was used as a mixture of the two diastereomers since they could not be separated by HPLC.
23. m.
24. J. M. Robertson, J. Chem. Soc. 1939, 232-236.