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. 1979 Apr;6(4):1709–1719. doi: 10.1093/nar/6.4.1709

Synthesis and coding properties of dinucleoside diphosphates containing alky pyrimidines which are formed by the action of carcinogens on nucleic acids.

B Singer, R G Pergolizzi, D Grunberger
PMCID: PMC327802  PMID: 156350

Abstract

Dinucleoside diphosphates of the general type pGpN have been prepared enzymatically using ribonuclease N1. Alkylated uridines or cytidines, which are products of carcinogens acting on nucleic acids, were tested in dinucleoside diphosphates for their ability to stimulate the binding of Ala- or Val-tRNA to ribosomes. O2-Ethyl C and 3-methyl C functioned as U, but not as C. In contrast, 3-methyl U behaved as C, but not as U. Both O2 and O4-ethyl U could be recognized as C or U, although binding in both cases was weak. Thus, modifications of the hydrogen-bonding sites of U or C causes miscoding and could be considered to represent mutagenic reactions.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Gassen H. G., Schetters H., Matthaei H. Codon-anticodon interaction studied with oligonucleotides containing 3 -deazauridine, 4 -deoxyuridine or 3 -deaza- 4 -deoxyuridine. II. Ribosome binding of oligonucleotides and phenylalanyl-tRNA. Biochim Biophys Acta. 1972 Jul 31;272(4):560–567. doi: 10.1016/0005-2787(72)90511-4. [DOI] [PubMed] [Google Scholar]
  2. Gerchman L. L., Ludlum D. B. The properties of O 6 -methylguanine in templates for RNA polymerase. Biochim Biophys Acta. 1973 May 10;308(2):310–316. doi: 10.1016/0005-2787(73)90160-3. [DOI] [PubMed] [Google Scholar]
  3. Giziewicz J., Shugar D. Preparative enzymic synthesis of nucleoside-5'-phosphates. Acta Biochim Pol. 1975;22(1):87–98. [PubMed] [Google Scholar]
  4. Grunberger D., Ward D. C., Reich E. 7-Deazanebularin. Coding properties of triplets and polynucleotides. J Biol Chem. 1972 Feb 10;247(3):720–724. [PubMed] [Google Scholar]
  5. Grünberger D., Holý A., Sorm F. Effect of 5'-terminal phosphate on the recognition of some dinucleoside phosphates by [14C]aminoacyl-tRNA. Biochim Biophys Acta. 1968 Apr 22;157(2):439–442. doi: 10.1016/0005-2787(68)90104-4. [DOI] [PubMed] [Google Scholar]
  6. Holý A., Grünberger D., Sorm F. Effect of 5'-substitution on the template activity of oligo-nucleotides for the binding of valine and alanine tRNA to ribosomes. Biochim Biophys Acta. 1970 Oct 15;217(2):332–345. doi: 10.1016/0005-2787(70)90531-9. [DOI] [PubMed] [Google Scholar]
  7. Kuśmierek J. T., Singer B. Reaction of diazoalkanes with 1-substituted 2, 4-dioxopyrimidines. Formation of O2, N-3 and O4-alkyl products. Nucleic Acids Res. 1976 Apr;3(4):989–1000. doi: 10.1093/nar/3.4.989. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Lagerkvist U. "Two out of three": an alternative method for codon reading. Proc Natl Acad Sci U S A. 1978 Apr;75(4):1759–1762. doi: 10.1073/pnas.75.4.1759. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Ludlum D. B. Alkylated polycytidylic acid templates for RNA polymerase. Biochim Biophys Acta. 1970 Jul 16;213(1):142–148. doi: 10.1016/0005-2787(70)90015-8. [DOI] [PubMed] [Google Scholar]
  10. Ludlum D. B. Methylated polydeoxyribocytidylic acid templates for RNA polymerase. Biochim Biophys Acta. 1971 Oct;247(3):412–418. doi: 10.1016/0005-2787(71)90027-x. [DOI] [PubMed] [Google Scholar]
  11. Ludlum D. B., Wilhelm R. C. Ribonucleic acid polymerase reactions with methylated polycytidylic acid templates. J Biol Chem. 1968 May 25;243(10):2750–2753. [PubMed] [Google Scholar]
  12. NIRENBERG M. W., MATTHAEI J. H. The dependence of cell-free protein synthesis in E. coli upon naturally occurring or synthetic polyribonucleotides. Proc Natl Acad Sci U S A. 1961 Oct 15;47:1588–1602. doi: 10.1073/pnas.47.10.1588. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. NIRENBERG M., LEDER P. RNA CODEWORDS AND PROTEIN SYNTHESIS. THE EFFECT OF TRINUCLEOTIDES UPON THE BINDING OF SRNA TO RIBOSOMES. Science. 1964 Sep 25;145(3639):1399–1407. doi: 10.1126/science.145.3639.1399. [DOI] [PubMed] [Google Scholar]
  14. SZER W., SHUGAR D. The preparation and properties of high molecular weight polymers of N-methyluridylic acid. Acta Biochim Pol. 1961;8:235–249. [PubMed] [Google Scholar]
  15. Singer B. All oxygens in nucleic acids react with carcinogenic ethylating agents. Nature. 1976 Nov 25;264(5584):333–339. doi: 10.1038/264333a0. [DOI] [PubMed] [Google Scholar]
  16. Singer B., Fraenkel-Conrat H., Kuśmierek J. T. Preparation and template activities of polynucleotides containing O2- and O4-alkyluridine. Proc Natl Acad Sci U S A. 1978 Apr;75(4):1722–1726. doi: 10.1073/pnas.75.4.1722. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Singer B., Fraenkel-Conrat H. Messenger and template activities of chemically modified polynucleotides. Biochemistry. 1970 Sep 15;9(19):3694–3701. doi: 10.1021/bi00821a007. [DOI] [PubMed] [Google Scholar]
  18. Singer B., Kröger M., Carrano M. O2- and O4-alkyl pyrimidine nucleosides: stability of the glycosyl bond and of the alkyl group as a function of pH. Biochemistry. 1978 Apr 4;17(7):1246–1250. doi: 10.1021/bi00600a018. [DOI] [PubMed] [Google Scholar]
  19. Singer B. O2-alkylcytidine--a new major product of neutral, aqueous reaction of cytidine with carcinogens. FEBS Lett. 1976 Mar 15;63(1):85–88. doi: 10.1016/0014-5793(76)80200-1. [DOI] [PubMed] [Google Scholar]
  20. Singer B. The chemical effects of nucleic acid alkylation and their relation to mutagenesis and carcinogenesis. Prog Nucleic Acid Res Mol Biol. 1975;15(0):219–284. [PubMed] [Google Scholar]
  21. Uchida T., Funayama-Machida C. Systematic synthesis of dinucleotides and trinucleotides with RNases U2, N1, and a non-specific RNase from B. subtilis. J Biochem. 1977 May;81(5):1237–1246. [PubMed] [Google Scholar]

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