Synthesis and application of novel nucleoside phosphonates and phosphoramidites modified at the base moiety

• Autorzy: Seela F. , Chen Y. , Melenewski A. , Rosemeyer H. , Wei C.
• Języki publikacji: EN

Abstrakty

EN

The H-phosphonates and phosphoramidites of 2'-deoxyisoguanosine, 2'-deoxy- isoinosine, 5-aza-7-deaza-2'-deoxyguanosine, and \:1-methyl-2'-deoxyformycin A were prepared. The diphenylcarbamoyl group was chosen for the 2-O-protection of 2'-deoxyisoinosine and 2'-deoxyisoguanosine, and dimethylaminoalkylidene groups were used to block the amino function of the various monomers. The synthesis of isoguanine oligonucleotides was found to be much more efficient using the 2-O-protected building blocks compared to those without oxygen protection. Oligodeoxynucleotides containing 2-deoxyisoguanosine and 2'-deoxycytidine form parallel duplex structures. The self-complementary duplex containing 5-aza-7-deaza- 2'-deoxyguanosine and 2'-deoxycytidine forms a stable duplex in acidic solution (pH = 5.0) while it is destabilized under neutral conditions.

Słowa kluczowe

EN

oligodeoxyribonucleotide; nucleoside phosphonate; 2'-deoxyisoinosine; 2'-deoxyisoguanosine; 5-aza-7-deaza-2'-deoxyguanosine; N-methyl-2'-deoxyformycin

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 1996
• Tom: 43
• Numer: 1
• Opis fizyczny: p.45-52,fig.

Twórcy

autor

Seela F.

• Universitat Osnabruck, Barbarastr.7, D-49069 Osnabruck, Germany

autor

Chen Y.

autor

Melenewski A.

autor

Rosemeyer H.

autor

Wei C.

Bibliografia

• 1. Uhlmann, E. & Peyman, A. (1990) Antisense oligonucleotides: A new therapeutic principle. Cheni. Rev. 90,543-584.
• 2. Sanghvi, Y. & Cook, D.P. (1994) Carbohydrate modifications in antisense research. ACS Symposium Scries, vol. 580, American Chemical Society, Washington, DC.
• 3. Seela, F. & Thomas, H. (1995) Duplex stabilization of DNA: Oligonucleotides containing 7-substitu- ted 7-deazaadenines. Hclv. Chim. Acta 78,94-108.
• 4. Seela, F., Ramzaeva, N. & Chen, V. (1995) Oligo­nucleotide duplex stability controlled by the 7- substituents of 7-deazaguanine 2'-deoxyribonu- cleosides. Bioorg. Med. Chcm. Lett. 24,3049-3052.
• 5. Seela, F., VVei,C. & Kazimierczuk, 7.. (1995)Subs- tituent reactivity and tautomensm of isoguano- sine and related nucleosides. Helv. Chim. Acta, 78,1843-1854.
• 6. Tuschl, T., Ng, M.M.P., Pieken, W., Benseler, F. & Eckstein, F. (1993) Importance of exocylic base functional groups of central core guanosines for hammerhead ribozyme activity. Biochemistry, 32, 11658-11668.
• 7. Seela, F. & Chen, Y. (1995) Oligonucleotides con­taining fluorescent 2 -deoxyisoinosine: solid- -phase synthesis and duplex stability. Nucleic Acids Res. 23, 2499-2505.
• 8. Switzer. C.Y., Moroney, S.E. & Benner, S.A. (1993) Enzymatic recognition of the base pair between isoevtidine and isoguanosine. Bio­chemistry 32,10489-10496.
• 9. Kamimura, T., Tsuchiya, M, Koura, K., Sckine. M. & Hata, T. (1983) DiphenylcarbamoyI and propionyl groups: A new combination of protecting groups for the guanine residue. Tetrahedron Lett. 24, 2775-2278.
• 10. McBride, L.J., Kierzek, R.( Beaucage, S.L & Caru- thers, M-H. (1986) Amidine protecting groups for oligonucleotide synthesis. /. Am. Chan. Soc. 108, 2040-2048.
• 11. Wierzchowski, J. & Shugar, D. (1982) Lumines­cence studies on formycin, its aglycone, and their N-methvI derivatives: Tautomensm, sites of protonation and phototautomerism. Photo- chcm. Photobiol. 35,445-458.
• 12. Prusiner, P., Brennan, T. & Sundaralingam, M. (1973) Crystal structure and molecular confor­mation of formycin monohydrates. Possible ori­gin of the anomalous circular dichroic spectra in formycin mono- and polvnuclcotides. Biochemi st ry 12, 1196-1201.
• 13. Ward, D.C. & Reich, E. (1968) Conformational properties of polyformycin: A polyribonucleo­tide with individual residues in the syn-confor- mation. Proc. Natl. Acad. Sci. U.S.A. 61,1494 1501.
• 14. Revankar, G.R., Hogan, M.E., Rao, T.S. & Shroff, H.N. (1992) Purine base modified 2'-deoxy- ribonucleosides, use in triplex forming oligo­nucleotides and process for preparing the same. PCT Application, PCT/US92/04795, 10.12.1992.
• 15. Uesugi, S., Tezuka, T. & Ikehara, M. (1975) Hybridization of polymers of antibiotic C-nu- cleoside phosphates, poly(formycin phosphate) and poly(laurusin phosphate). Biochemistry 14, 2903-2906.
• 16. Cho, B.P. & McGregor, M.A. (1994) Tauto- merism, protonation, and ionization of formycin in aqueous solution by the pH dependence of1 C chemical shifts and ,3C- H coupling constants. Nucleosides & Nucleotides 13, 481-490.
• 17. Zemlicka, J. (1975) Formycin anhydronu- cleosides. Conformation of formycin and con­formational specificity of adenosine deaminase. /. Am. Chem. Soc. 97, 5896-5903.
• 18. Brechbuhler, H., Biichl, H., Hatz, E., SchreiberJ. & Hschenmoser, A. (1965) Die Reaktion von Carbonsauren nut Acetalen des N,N-Dimethvl- formamids: Fine Veresterungsmethode. Helv. Chim. Acta 7,1746-1771.
• 19. Rosowsky, A., Solan, V.C. & Gudas, L.J. (1985) Improved synthesis of 2'-deoxvformvcin A and studies of its in vitro activity against mouse lym­phoma of T-cell origin. /. Med. Chem. 28, 1096- 1099.
• 20. Giziewicz, G„ De Clercq, b., Luczak, M. & Shu­gar, D. (1975) Antiviral and antimetabolic activi­ties of formycin and its .V1-, N2-, 2'-O-, and 3'-0- methylated derivatives. Biochem. Pharmacol. 24, 1813—1817.
• 21. Chenon, M.-T., Panzica, R.P., Smith, J.C., Pugmi- re, R.J., Grant, D.M. & Townsend, L.B. (1976) Carbon-13 magnetic resonance spectra of C-nu- cleosides. Tautomerism in formycin and formy­cin B and certain pyrazolo(4/3-dlpvrimidines. /. Am. Chem. Soc. 98, 4736-4745.
• 22. Rosemever, H. & Seela, F. (1987) 5-Aza-7-deaza- 2'-deoxvguanosine: Studies on the glvcosylation of weakly nuclcophilic imidazo[l,2-al-s-triazinyl anions. /. Org. Chem. 52,5136-5143.
• 23. Roy, K.B. & Miles, H.T. (1983) Tautomerism and ionization of xanthosine. Nucleosides & Nucleotides 2, 231-242.
• 24. Eriljy, R., Horowitz, D.M., Walker, P.A., Ziehler-Martin, J.P., Boosalis, MS., Goodman. M.F., Itakura, K. & Kaplan, B.E. (1986) Synthesis and properties of oligonucleotides containing 2'- deoxynebularineand 2'-deoxyxanthosine, Nucleic Acids Res. 14,8135-S153.