The utilization of secondary phosphine oxide synthons for the preparation of novel tertiary phosphine oxide modified DNA

Synlett

Volumn , Issue 3, 1998, Pages 283-285

  Collingwood, Stephen P ^a   Taylor, Roger J ^a  

^a Novartis Pharmaceutical Central Research   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003012871     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1632     Document Type: Article

References (16)

1. Szymkowski, D.E.; Drug Development Tech., 1996, 1, 415.
2. Altmann, K.-H., Fabbro, D.; Dean, N. M.; Geiger, T.; Monia, B. P.; Müller, M.; Nicklin, P. Biochem. Soc. Trans.,1996, 24, 630.
3. Baxter, A. D.; Baylis, E. K.; Collingwood, S. P.; Taylor, R. J.; Weetman, J. EP 629633, 1994.
4. Hall, R. G.; Riebli, P. EP 501702, 1991.
5. Baylis, E. K.; Tetrahedron Lett., 1995, 36, 9385.
6. Collingwood, S. P.; Baxter, A. D. Synlett, 1995, 703.
7. Hays, H. R. J. Org. Chem., 1968, 33, 3690.
8. Compound 5 was prepared by a directly analogous route to that described by Xu, Y.; Wei, H.; Xia, J. Liebigs Ann. Chem., 1988, 1139.
9. Tanaka, H.; Fukui, M.; Haraguchi, K.; Maskai, M.; Miyasaka, T. Tetrahedron Lett., 1989, 30, 2567.
10. Sanghvi, Y. S.; Ross, B.; Bharadwaj, R.; Vasseur, J-J. Tetrahedron Lett., 1994, 35, 4697;
11. Sanghvi, Y. S.; Bharadwaj, R.; Debart, R; De Mesmaeker, A. Synthesis, 1994, 1163.
12. Each oligonucleotide was prepared on an ABI 390 DNA synthesiser using standard phosphoramidite chemistry according to : Gait, M. J.; Oligonucleotide Synthesis: A Practical Aproach, IRL Press, Oxford, 1984.
13. Pieles, U.; Zürcher, W.; Schär, M.; Moser, H. Nucleic Acids Res., 1993, 21, 3191.
14. The thermal denaturation of DNA/RNA duplexes was monitored at 260 nm using a Gilford Response II spectrophotometer. Absorbance vs temperature profiles were measured at 0.004mM of each strand in 10mM phosphate pH 7.0 (Na Salts), 100mM total (Na+) 0.1mm EDTA. Tm's were obtained from fits of absorbance vs. temperature curves to a two state model with linear slope baselines (Freier, S. M.; Albrego.; T. D.; Turner, D. H. Biopolymers, 1992, 22, 1107.) All values are averages of at least three experiments. The absolute error of the Tm values is +-0.5°C.
15. Lesnikowski, Z. L.; Jaworska, M.; Stec, W. J. Nucl. Acids Res., 1990, 18, 2109;
16. Milligan, J. F.; Matteucci, M. D.; Martin, J. C. J. Med. Chem., 1993, 36, 1923.