Photoisomerization of 2′-deoxyribofuranosyl and ribofuranosyl 2-phenylazoimidazole

Tetrahedron Letters

Volumn 44, Issue 36, 2003, Pages 6903-6906

  Endo, Masayuki ^a   Nakayama, Koji ^a   Kaida, Yuka ^a   Majima, Tetsuro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 N (2' DEOXYRIBOFURANOSYL) 2 PHENYLAZOIMIDAZOLE; 1 N RIBOFURANOSYL 2 PHENYLAZOIMIDAZOLE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CIS ISOMER; IRRADIATION; ISOMERISM; PHOTOACTIVATION; SYNTHESIS; TRANS ISOMER;

EID: 0042659737     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01697-6     Document Type: Article

References (21)

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11. In the differential NOE spectrum of the product 2 irradiated at C1′ proton, 2″H, 4′H and 5H were enhanced, which is identical to a β-anomer. On the other hand, 2′H, 3′H and 5H were enhanced for the counterpart diastereomer of 2, which is identical to an α-anomer.
12. +.
13. In the differential NOE spectrum of nucleoside 5 irradiated at C1′ proton, 2′H, 4′H, 5H and aromatic protons were enhanced, which is identical for a β-anomer.
14. +.
15. Anzai J., Osa T. Tetrahedron. 50:1994;4039-4070.
16. Photo irradiation was carried out in a 1.0 mL of methanoic solution containing 20 μM of nucleoside 3 or 5 by using a 500 W ultra high pressure mercury lamp (Ushio USH-500D; 500 W) equipped with a monochrometor (Ritsuoyo Kogaku MC-10N) which can control specific wavelength within 4 nm full-width at half maximum. A quartz cell with 1 cm path length was used and the sample was cooled to 0°C in a cell holder equipped with a circular temperature controller. UV/vis spectra were obtained at 0°C.
17. The quantum yields for trans to cis isomerization of nucleoside 3 and 5 were measured at rt referring to the quantum yields of trans to cis and cis to trans photoisomerizations of azobenzene (Φ=0.14 and 0.42, respectively) as standard.
18. Ronayette J., Arnaud R., Lebourgeois P., Lemaire J. Can. J. Chem. 52:1974;1848-1857.
19. 1/2=5.4 h), respectively.
20. 3OD solution containing 20 mM of 3 in an NMR tube using a UV transilluminator (UVP LMS-20E; 40 W) at 365 nm on ice.
21. Conversion from the cis to trans isomer was carried out in the same NMR sample by irradiation using the same ultra high-pressure mercury lamp with a UV cut-off filter below 430 nm wavelength (Sigma Koki UTF-50-43Y cut-off filter).