[(2-Deoxy-α-and β-d-erythro-pentofuranosyl)thymin-1-yl] methane derivatives as potential conformational probes for altDNA oligonucleotides

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 2, 1996, Pages 207-212

  Scremin, Carlo L ^a   Boal, Jila H ^a   Wilk, Andrzej ^a   Phillips, Lawrence R ^b   Beaucage, Serge L ^a  

^a CENTER FOR BIOLOGICS EVALUATION AND RESEARCH   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEMENTARY DNA; OLIGONUCLEOTIDE; THYMINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030050537     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(95)00589-L     Document Type: Article

References (16)

1. Koga, M.; Wilk, A.; Moore, M. F.; Scremin, C. L.; Zhou, L.; Beaucage, S. L. J. Org. Chem. 1995, 60, 1520.
2. Koga, M.; Geyer, S. J.; Regan, J. B., Beaucage, S. L. Nucl. Acids Res. Symp. Ser. No. 29 1993, 3.
3. Koga, M.; Moore, M. F.; Beaucage, S. L. J. Org. Chem. 1991, 56, 3757.
4. Scremin, C. L.; Boal, J. H.; Wilk, A.; Phillips, L. R.; Zhou, L.; Beaucage, S. L. Tetrahedron Lett. 1995, 36, 8953.
5. Hybrid simulations were achieved using QUANTA version 4.0 with helix constraints in vacuum. The lowest energy conformation was further energy-minimized using the Adopted Basis Newton-Raphson method. Figure 1 should be viewed with a stereoviewer.
6. In spite of structural homologies between 1a,b and 2a,b, the preparation of these nucleoside analogues has been achieved according to quite different synthetic strategies.
7. Hoffer, M. Chem. Ber. 1960, 93, 2777.
8. 8b
9. (b) Kolb, A.; Huynh Dinh, T.; Igolen, J. Bull. Soc. Chim. France 1973, 3447.
10. 3): δ 21.7, 35.5, 43.3, 64.1, 75.5, 75.9, 82.4, 126.5, 126.7, 129.2, 129.6, 143.9, 144.2, 165.9, 166.4.
11. Shealy, Y. F.; O'Dell, C. A.; Thorpe, M. C. J. Het. Chem. 1981, 18, 383.
12. Shaw, G.; Warrener, R. N. J. Chem. Soc. 1958, 153.
13. +): 493.1975. Found: 493.1977.
14. 2′-H″ are defined according to Wood, D. J.; Hruska, F. E.; Ogilvie, K. K. Can. J. Chem. 1974, 52, 3353.
15. Barone, A. D.; Tang, J. -Y; Caruthers, M. H. Nucl. Acids Res. 1984, 12, 4051.
16. 3); δ 147.2 and 147.1 ppm.