Synthesis of 4-guanidinopyrimidine nucleosides for triple helix-mediated guanine and cytosine recognition

Tetrahedron Letters

Volumn 39, Issue 7, 1998, Pages 547-550

  Doronina, Svetlana O ^a   Behr, Jean Paul ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYTIDINE; CYTOSINE; GUANINE; PYRIMIDINE NUCLEOSIDE; THYMIDINE;

ARTICLE; DNA SEQUENCE; GEOMETRY; SYNTHESIS;

EID: 0032509935     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10627-X     Document Type: Article

References (25)

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8. 5. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2502; Dutta, S. P.; Chheda, G. B. in Nucleic Acid Chemistry, part 4; Townsend, L. B.; Tipson, R. S.; John Wiley and Sons, Inc.: New York, 1991; pp. 245-247.
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13. 8. For N-nucleophiles see Perbost, M.; Sanghvi, Y. S. J. Chem. Soc., Perkin Trans. 1 1994, 2051-2052. For O-nucleophiles, Xu, Y.-Z.; Swann, P. F. Nucleic Acids Res. 1990, 18, 4061-4065. For C-nucleophiles, ref. 6.
14. 3O-phenyl), 7.18-7.44 (m, 12H, phenyl), 7.84 (s, 1H, H6).
15. 3O-phenyl), 7.15-7.46 (m, 12H, phenyl), 7.64 (s, 1H, H6).
16. 11. Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933-5936.
17. 1H NMR of 7 showed no resonance for H5 whereas H6 still gave a doublet (J = 7.5 Hz). The H5/H6 proton correlation peak was also absent from the COSY spectrum. Variable temperature spectra showed evidence for hindered rotation about N4-C(S) bond. Two isomers in an equimolar ratio were observed in the 230°K spectrum.
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20. 2-), 13.6 (B) and 15.9 (A) (bs, 1H, NH-CO).
21. 3), 2.02-2.16 and 2.32-2.47 (2m, 2H, H2′, H2″), 3.67-3.98 (m, 3H, H5′, H5″, H4′), 4.39 (m, 1H, H3′), 5.88 (d, J = 7.4 Hz, H5), 6.27 (dd, 1H, J = 5.8 Hz, H1′), 7.96 (d, 1H, J = 7.4 Hz, H6).
22. 3O-phenyl), 7.15-7.46 (m, 12H, phenyl), 7.64 (s, 1H, H6).
23. 3O-phenyl), 7.15-7.43 (m, 13H, H6, phenyl).
24. 3), δ (ppm): 149.19, 149.39 (ß); 149.74, 150.05 (α).
25. 20. Taylor, P. J.; Wait, A. R. J. Chem. Soc., Perkin Trans. 2 1986, 1765-1770.