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. 1990 Oct 11;18(19):5729–5734. doi: 10.1093/nar/18.19.5729

Synthesis and characterization of oligodeoxynucleotides containing the mutagenic base analogue 4-O-ethylthymine.

D Fernandez-Forner 1, Y Palom 1, S Ikuta 1, E Pedroso 1, R Eritja 1
PMCID: PMC332307  PMID: 2216766

Abstract

A method for the preparation of oligonucleotides containing the mutagenic base 4-O-ethylthymine is described for the first time. Use of p-nitrophenylethyl type base protecting groups together with phosphitetriester solid-phase methodology makes possible the rapid and efficient preparation of oligonucleotides bearing 4-O-ethylthymine, while standard base protecting groups are not compatible with the presence of this base. Possible applications of this methodology are discussed.

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Selected References

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

  1. Borowy-Borowski H., Chambers R. W. A study of side reactions occurring during synthesis of oligodeoxynucleotides containing O6-alkyldeoxyguanosine residues at preselected sites. Biochemistry. 1987 May 5;26(9):2465–2471. doi: 10.1021/bi00383a010. [DOI] [PubMed] [Google Scholar]
  2. Borowy-Borowski H., Chambers R. W. Solid-phase synthesis and side reactions of oligonucleotides containing O-alkylthymine residues. Biochemistry. 1989 Feb 21;28(4):1471–1477. doi: 10.1021/bi00430a007. [DOI] [PubMed] [Google Scholar]
  3. Connolly B. A., Newman P. C. Synthesis and properties of oligonucleotides containing 4-thiothymidine, 5-methyl-2-pyrimidinone-1-beta-D(2'-deoxyriboside) and 2-thiothymidine. Nucleic Acids Res. 1989 Jul 11;17(13):4957–4974. doi: 10.1093/nar/17.13.4957. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Dolan M. E., Oplinger M., Pegg A. E. Use of a dodecadeoxynucleotide to study repair of the O4-methylthymine lesion. Mutat Res. 1988 Mar;193(2):131–137. doi: 10.1016/0167-8817(88)90043-0. [DOI] [PubMed] [Google Scholar]
  5. Li B. F., Reese C. B., Swann P. F. Synthesis and characterization of oligodeoxynucleotides containing 4-O-methylthymine. Biochemistry. 1987 Feb 24;26(4):1086–1093. doi: 10.1021/bi00378a015. [DOI] [PubMed] [Google Scholar]
  6. Nielsen J., Taagaard M., Marugg J. E., van Boom J. H., Dahl O. Application of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite for in situ preparation of deoxyribonucleoside phosphoramidites and their use in polymer-supported synthesis of oligodeoxyribonucleotides. Nucleic Acids Res. 1986 Sep 25;14(18):7391–7403. doi: 10.1093/nar/14.18.7391. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Pegg A. E. Formation and metabolism of alkylated nucleosides: possible role in carcinogenesis by nitroso compounds and alkylating agents. Adv Cancer Res. 1977;25:195–269. doi: 10.1016/s0065-230x(08)60635-1. [DOI] [PubMed] [Google Scholar]
  8. Saffhill R., Margison G. P., O'Connor P. J. Mechanisms of carcinogenesis induced by alkylating agents. Biochim Biophys Acta. 1985 Dec 17;823(2):111–145. doi: 10.1016/0304-419x(85)90009-5. [DOI] [PubMed] [Google Scholar]
  9. 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]
  10. Singer B. O-alkyl pyrimidines in mutagenesis and carcinogenesis: occurrence and significance. Cancer Res. 1986 Oct;46(10):4879–4885. [PubMed] [Google Scholar]
  11. Webb T. R., Matteucci M. D. Hybridization triggered cross-linking of deoxyoligonucleotides. Nucleic Acids Res. 1986 Oct 10;14(19):7661–7674. doi: 10.1093/nar/14.19.7661. [DOI] [PMC free article] [PubMed] [Google Scholar]

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