Hybridization properties of oligonucleotides bearing a tricyclic 2'- deoxycytidine analog based on a carbazole ring system

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5057-5060

  Matteucci, Mark D ^a   Von Krosigk, Ulrike ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; DEOXYCYTIDINE; OLIGONUCLEOTIDE; PHENOXAZINE DERIVATIVE;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; DATA ANALYSIS; DNA SYNTHESIS; DRUG STABILITY; DRUG SYNTHESIS; HYBRIDIZATION; RNA SYNTHESIS;

EID: 0030586192     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01016-7     Document Type: Article

References (11)

1. 1. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York. 1984; pp. 132-133.
2. 2. Lin, K-Y.; Jones, R.J.; Matteucci, M. J. Am. Chem. Soc. 1995, 117, 3873-3874.
3. 3. Stille, J.K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
4. 4. Gómez-Bengoa, E.; Echavarren, A.M. J. Org. Chem. 1991, 56, 3497-3501.
5. 5. Ti, G.S.; Gaffney, B.L.; Jones, R.A. J. Am. Chem. Soc. 1982, 104, 1316-1319.
6. 6. Gaffney, B.L.; Jones, R.A. Tetrahedron Lett. 1982, 23, 2253.
7. 3): 9.00 (s, 1H); 7.60 (d, 1H); 7.49 (d, 2H); 7.38 (d, 4H); 7.30-7.20 (m, 4H); 6.86 (t, 1H); 6.79 (d, 4H); 6.63 (m, 2H); 4.62 (m, 1H); 4.31 (m, 1H); 3.70, 3.69 (2s, 6H); 3.61 (dd, 1H); 3.39 (dd, 1H); 2.97 (m, 1H); 2.76 (br, 1H); 2.43 (m, 1H).
8. 2O/pyr (1/1) yielding exclusively the monoacetylated 3′ ester. This hydroxyl-protected derivative was stable to the H-phosphonate coupling conditions of TEAH salt of ethyl H-phosphonate (0.05M) and pivaloyl chloride (0.25M) in pyridine at 20°C for at least 1 hr.
9. P-NMR (200MHz, D2O): 3.205.
10. 10. Froehler, B.C.; Ng, P.G.; Matteucci, M.D. Nucleic Acids Res. 1986, 14, 5399.
11. 11. Eadie, J.S.; McBride, L.J.; Efcavitch, J.W.; Huff, L.B.; Cathcart, R. Anal. Biochem. 1987, 165, 442.