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1996 | 43 | 1 |

Tytuł artykułu

Miscoding properties of isoguanine [2-oxoadenine] studied in an AMV reverse transcriptase in vitro system

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
We have found that isoguanine (¡G) can pair with thymine (iG T) and the non- natural base, 5-methylisocytosine (iG x iCM) during template directed synthesis catalyzed by AMV reverse transcriptase. The ratio of these pairings is about 1:10, irrespectively which of the templates, poly(C,iG) or poly(I,iG) is used. This ratio corresponds to the ratio of 2-OH and 2-keto tautomers in monomer in aqueous sol ution and apparently it is not influenced by the template context. Our results indicate also that formation of the reverse transcriptase catalyzed base pairs between iG and A, G or C can occur only at a low frequency, comparable to the frequency, of mismatches of.

Wydawca

-

Rocznik

Tom

43

Numer

1

Opis fizyczny

p.247-254,fig.

Twórcy

  • Polish Academy of Sciences, A.Pawinskiego 5A, 02-106 Warsaw, Poland

Bibliografia

  • 1. Cherbuiiez, E. & Bernhard, K. (1932) Recherches sur la graine de croton. 1. Sur le crotonoside (2-oxy-6-amino-purine-d-riboside). Helv. Chini. Acta 15.464-471.
  • 2. Fuhrman, F.A.. Furhman, G.J.. Nachman, R.j. & Mosher, H.S. (1981) lsoguanosine: isolation from an animal. Sciencc 212,557-558.
  • 3. Bergmann. W. & Burke. D.C. (1956) Contri­butions to the study of marine products. XL. The nucleosides of sponges. IV. Spongosine. ). Or$. Chern. 21,226-228.
  • 4. Olinski, R., Zastawny, T., Budzbon. J., Sko- kowski.J.. Zegarski, W. & Dizdaroglu, M. (1992) DNAbase modifications in chromatin of human cancerous tissues. FEBS Lett. 309, 193-198.
  • 5. Shibutani. 5., Takeshita, M. & GroIIman, A.P. (1991) Insertion of specific bases during DNA synthesis past the oxidation-damaged base S-oxodG. Nature (London) 349, 431-434.
  • 6. Maki, H. & Sekiguchi, M. (1992) Mut'l protein specifically hvdrolyses a potent mutagenic substrate for DNA synthesis. Nature (London) 355, 273-275.
  • 7. SepioL )., Kazimierczuk, Z. & Shugar, D. (1976) Tautomerism of isoguanine and solvent- induced keto-enol equilibrium. /.. Naturforsch. 31c, 361-370.
  • 8. Switzer, C.Y., Moroney, 5.E. & Benner, S.A. (1993) Enzymatic recognition of the base pair between isocytidine and isoguanosine. Biochemistry 32, 10489-10496.
  • 9. Kusmierek. J.T. & Shugar, D. (1978) A new route to 2'(3')-0 alkyl purine nucleosides. NucLic Acids Res. Special Publ. N° 4,73-77.
  • 10. Brown, D.M., Todd, A.R. & Varadarajan, S. (1957) Nucleotides. Part XL. Q2:5'-cyclouridine and a synthesis of isoevtidine. /. Chetn. Soc. 868-872.
  • 11. l.in, T.S., Neenan,J.P.,Cheng, YC. Prusotl. W.H. & Ward, D.C. (1976) Synthesis and antiviral activity of 5- and 5'-substituted thymidine analogs. /. Med. Chew. 19, 495-498.
  • 12. Giziewicz, ). & Shugar, D. (1975) Preparative enzvmic synthesis of nucleosideo'-phosphates. Acta Biodtim. Polon. 22,87-98.
  • 13. Moffatt, J.B. & Khorana, H.G.U961) Nucleoside polyphosphates. X. The synthesis and some reactions of nucleoside-5'-phosphoromorpho- lidates and related compounds. Improved methods for the preparation of nucleoside- 5'-poiyphosphates. J. Am. Chetn. Soc. 83, 649-658.
  • 14. Mroczkowska. M.M. & Kusmierek, J.T. (1991) Miscoding potential of N~,3-ethenoguanine studied in an Escherichia coli DNA-dependent RNA polymerase in vitro system and possible role of this adduct in vinyl chloride-induced mutagenesis. Mutagenesis 6, 385-390.
  • 15. Mroczkowska, M.M. & Kusmierek. J.T. (1993) The effect of neighboring bases on miscoding properties of N",3-ethenoguanine. Z. Nautr- forsch. 48c, 63-68.
  • 16. Battula, & Loeb, L.A. (1974) The infidelity of avian myeloblastosis virus deoxyribonucleic acid polymerase in polynucleotide replication. /. Biol. Chern. 249,4086-4093.
  • 17. Singer, B., Spengler, S.J., Chavez, F. & Kusmierek, J.T. (1987) The vinyl chloride-derived nucleoside. N ,3-ethenoguanosine is a highly efficient mutagen in transcription. Carcinogenesis 8. 745-747.
  • 18. Singer. B. k Spengler. S. (1982) Reaction of O-methylhydroxylamine with adenosine shifts tautomeric equilibrium to cause transitions. FEBS Lett. 139,69-71.
  • 19. Kamiya. H., Ueda. T.,Ohgi, T., Matsukage, A. & Kasai, H. (1995) Misiincorporation of dAMP opposite 2-hydroxvadenine, an oxidative form of adenine. Nucleic Acids Res. 23, 761-766.
  • 20. Kunkel, T.A. (1985) The mutational specificity of DNA polymerase-^ during in vitro DNA synthesis.'/. Biol. Chern. 260,5787-5796.
  • 21. Horn. T.. Chang, C.-A. & Collins, M.L. (1995) Hybridization properties of the 5-methyl-isocytidine/isoguanösine base pair in synthetic oligodeoxynucleotides. Tetrahedron Lett. 36, 2033-2036.

Typ dokumentu

Bibliografia

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Identyfikator YADDA

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