Photo-responsive oligonucleotides carrying azobenzene at the 2'-position of uridine

Tetrahedron Letters

Volumn 40, Issue 45, 1999, Pages 7995-7998

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Azo compounds; Isomerization; Phosphoramidites; Photochemistry

Indexed keywords

AZOBENZENE DERIVATIVE; COMPLEMENTARY DNA; OLIGONUCLEOTIDE; URIDINE;

ARTICLE; CHEMICAL MODIFICATION; CIS TRANS ISOMERISM; DRUG SYNTHESIS; PHOTOREACTIVITY;

EID: 0033527763     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01547-6     Document Type: Article

References (27)

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17. 4-Bromomethylazobenzene was synthesized according to the literature: Wesson, J. A.; Noh, I.; Kitano, T.; Yu, H. Macromolecules, 1984, 17, 782.
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19. 4′), 3.65-3.61 (m, 2H, H5′).
20. 4: calcd: 2565.4; observed: 2564.8.
21. 4 were eluted at 23.8 and 19.5 min, respectively.
22. m values were determined from the maximum in the first derivative of the melting curve.
23. The light from a 150 W Xenon lamp was irradiated for 10 min through an appropriate filter. Infrared light was cut off by using a water filter.
24. m measurements.
25. 8 duplex was lower than that of unmodified duplex. According to Yamana et al., the pyrene- or anthraquinone-modified uridine stabilized duplexes even when it was located in the middle of the sequence: Yamana, K.; Iwase, R.; Furutani, S.; Tsuchida, H.; Zako, H.; Yamaoka, T.; Murakami, A. Nucleic Acids Res. 1999, 27, 2387, and Yamana, K.; Mitsui, T.; Yoshioka, J.; Isuno, T.; Nakano, H. Bioconjugate Chem. 1996, 7, 715.
26. 8 duplex was lower than that of unmodified duplex. According to Yamana et al., the pyrene- or anthraquinone-modified uridine stabilized duplexes even when it was located in the middle of the sequence: Yamana, K.; Iwase, R.; Furutani, S.; Tsuchida, H.; Zako, H.; Yamaoka, T.; Murakami, A. Nucleic Acids Res. 1999, 27, 2387, and Yamana, K.; Mitsui, T.; Yoshioka, J.; Isuno, T.; Nakano, H. Bioconjugate Chem. 1996, 7, 715.
27. 8.