An uridine derivative containing a hydrophobic fluorescent probe at the 2'-position: Synthesis and its incorporation into oligonucleotides

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5815-5818

  Yamana, Kazushige ^a   Mitsui, Tuneo ^a   Hayashi, Haruhisa ^a   Nakano, Hidehiko ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYE; OLIGONUCLEOTIDE; URIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; FLUORESCENCE; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030878232     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01329-4     Document Type: Article

References (14)

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3. c) Hoenes, G.; Hauser, M.; Pleiderer, G. Photochem. Photobiol. 1986, 43, 133-137.
4. Yamana, K.; Ohashi, Y.; Nunota, K.; Nakano, H. Tetrahedron 1997, 53, 4265-4270.
5. a) Weber, G.; Farris, F.J. Biochemistry 1979, 18, 3075-3078.
6. b) Macgregor, R.B.; Weber, G. Nature 1986, 319, 70-73.
7. a) Haworth, R.D.; Sheldrick, G. J. Chem. Soc. 1934, 864-866.
8. b) reference 3a.
9. King, L.C. J. Org. Chem. 1944, 66, 894-896.
10. +N), 7.00(s, 1H, naphthyl), 7.34(dd, 1H, naphthyl), 7.78(d, 1H, naphthyl), 7.85(dd, 1H, naphthyl), 8.00(d, 1H, naphthyl), 8.27(t, 2H, pyridine), 8.57(s, 1H, naphthyl), 8.73(t, 1H, pyridine), 9.01(d, 2H, pyridine).
11. 1H, naphthyl), 7.25(dd, 1H, naphthyl), 7.66(d, 1H, naphthyl), 7.79(dd, 1H, naphthyl), 7.88(d, 1H, naphthyl), 8.37(s, 1H, naphthyl), 12.61(s, 1H, -COOH).
12. 3H).
13. The synthesis of the modified oligonucleotides was accomplished by phosphoramidite chemistry, beginning with 5′-DMT nucleoside (0.2 μmol) bound to a CPG support. For the coupling of normal deoxyribonucleoside phosphormaidites, the standard protocol (50 μL of 0.1 M amidite and 50 μL of 0.1 M tetrazole in acetonitrile, 2 min) was used. For the coupling of the modified amidites 5, 120 (μL of the 0.1 M amidite and 120 μL of 0.1 M tetrazole in acetonitrile (10 min) were used.
14. The TOF Mass spectra data obtained on a Broker ReflexII model using a linear negative mode; Oligomer 6 : 2646.7 (. 2646.9), 7 : 3857.6 (calcd. 3857.7), 8 :3857.7 (calcd. 3857.7), 9 : 3857.9 (calcd. 3857.7).