Photo-responsive oligonucleotides carrying azobenzene in the side- chains

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9015-9018

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Azo compound; Isomerization; Phosphoramidite; Photochemistry

Indexed keywords

AZOBENZENE DERIVATIVE; OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE;

ARTICLE; CELL FUNCTION; CHEMICAL MODIFICATION; CRYSTALLIZATION; ISOMERISM; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE METABOLISM; PHOTOCHEMISTRY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0032481070     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02022-X     Document Type: Article

References (12)

1. 1. a) Kume, A.; Fujii, M.; Sekine, M.; Hata, T. J. Org. Chem. 1984, 49, 2139.
2. b) Yamana, K.; Aota, R.; Nakano, H. Tetrahedron Lett., 1995, 36, 8427.
3. c) Giovannangeli, C.; Perrouault, L.; Escudé, C.; Thuong, N.; Hélène, C. Biochemistry, 1996, 35, 10539.
4. d) Boutorine, A.S.; Brault, D.; Takasugi, M.; Delgado, O.; Hélène, C. J. Am. Chem. Soc., 1996, 118, 9469.
5. e) Letsinger, R. L.; Wu, T. J. Am. Chem. Soc. 1994, 116, 811.
6. f) Kool, E. T. Chem. Rev., 1997, 97, 1473 and references cited therein.
7. 2. Yamana, K.; Yoshikawa, A.; Nakano, H. Tetrahedron Lett., 1996, 37, 637.
8. 3. Endo, M.; Azuma, Y.; Saga, Y.; Kuzuya, A.; Kawai, G.; Komiyama, M. J. Org. Chem., 1997, 62, 846.
9. 3, 109.4 MHz] δ 149.8, 149.3.
10. 5. The HPLC conditions: a Merck LiChrospher 100 RP-18(e) column, 260 nm, 1.0 ml/min, a linear gradient 5-25 % (25 min) acetonitrile/water containing 50 mM ammonium formate.
11. 6. The light from 150 W Xenon lamp was irradiated for 30 min through an appropriate filter. Infrared light was cut off by using water filter.
12. 7. The ci⇒trans conversion slowly proceeded even in dark (it took about 5 h to convert half of the oligonucleotide A to the C at 25°C).