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. 1991 Aug 25;19(16):4361–4369. doi: 10.1093/nar/19.16.4361

Solid-phase synthesis of DNA fragments containing the modified base 7-hydro-8-oxo-2'-deoxyguanosine.

H C Roelen 1, C P Saris 1, H F Brugghe 1, H van den Elst 1, J G Westra 1, G A van der Marel 1, J H van Boom 1
PMCID: PMC328621  PMID: 1886763

Abstract

The 5'-(4,4'-dimethoxytrityl) protected 3'-(2-cyanoethoxy)-N,N-diisopropylphosphoramidite of 7-hydro-8-oxo-2'-deoxy-guanosine, the exocyclic amino and lactam functions of which are protected with acetyl and diphenylcarbamoyl groups, respectively, has been prepared from the 8-bromo derivatives of deoxy- and riboguanosine. This synthon, in combination with standard d-nucleoside 3'-(2-cyanoethoxy)-N,N-diisopropylphosphoramidites, was applied successfully to a solid-phase synthesis. Well-defined oligodeoxyribonucleotides containing a 7-hydro-8-oxo-2'-deoxyguanosine residue at predetermined positions were obtained after deprotection with methanolic ammonia and purification by gel filtration.

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Selected References

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  1. Aida M., Nishimura S. An ab initio molecular orbital study on the characteristics of 8-hydroxyguanine. Mutat Res. 1987 Oct;192(2):83–89. doi: 10.1016/0165-7992(87)90101-1. [DOI] [PubMed] [Google Scholar]
  2. Ames B. N. Identifying environmental chemicals causing mutations and cancer. Science. 1979 May 11;204(4393):587–593. doi: 10.1126/science.373122. [DOI] [PubMed] [Google Scholar]
  3. Barton D. H., Hansen P. E., Picker K. Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 8. Synthesis and properties of O-alkyl selenoesters. J Chem Soc Perkin 1. 1977 Aug;15:1723–1730. [PubMed] [Google Scholar]
  4. Barton D. H., Subramanian R. Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 7. Conversion of thiocarbonates into deoxy-sugars. J Chem Soc Perkin 1. 1977 Aug;15:1718–1723. [PubMed] [Google Scholar]
  5. Chow F., Kempe T., Palm G. Synthesis of oligodeoxyribonucleotides on silica gel support. Nucleic Acids Res. 1981 Jun 25;9(12):2807–2817. doi: 10.1093/nar/9.12.2807. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Culp S. J., Cho B. P., Kadlubar F. F., Evans F. E. Structural and conformational analyses of 8-hydroxy-2'-deoxyguanosine. Chem Res Toxicol. 1989 Nov-Dec;2(6):416–422. doi: 10.1021/tx00012a010. [DOI] [PubMed] [Google Scholar]
  7. Floyd R. A. Role of oxygen free radicals in carcinogenesis and brain ischemia. FASEB J. 1990 Jun;4(9):2587–2597. [PubMed] [Google Scholar]
  8. Floyd R. A. The role of 8-hydroxyguanine in carcinogenesis. Carcinogenesis. 1990 Sep;11(9):1447–1450. doi: 10.1093/carcin/11.9.1447. [DOI] [PubMed] [Google Scholar]
  9. Gait M. J., Matthes H. W., Singh M., Sproat B. S., Titmas R. C. Rapid synthesis of oligodeoxyribonucleotides. VII. Solid phase synthesis of oligodeoxyribonucleotides by a continuous flow phosphotriester method on a kieselguhr-polyamide support. Nucleic Acids Res. 1982 Oct 25;10(20):6243–6254. doi: 10.1093/nar/10.20.6243. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Holland J., Holland I. B., Ahmad S. I. DNA damage by 8-methoxypsoralen plus near ultraviolet light (PUVA) and its repair in Escherichia coli: genetic analysis. Mutat Res. 1991 May;254(3):289–298. doi: 10.1016/0921-8777(91)90068-z. [DOI] [PubMed] [Google Scholar]
  11. Klein J. C., Bleeker M. J., Lutgerink J. T., van Dijk W. J., Brugghe H. F., van den Elst H., van der Marel G. A., van Boom J. H., Westra J. G., Berns A. J. Use of shuttle vectors to study the molecular processing of defined carcinogen-induced DNA damage: mutagenicity of single O4-ethylthymine adducts in HeLa cells. Nucleic Acids Res. 1990 Jul 25;18(14):4131–4137. doi: 10.1093/nar/18.14.4131. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Kouchakdjian M., Bodepudi V., Shibutani S., Eisenberg M., Johnson F., Grollman A. P., Patel D. J. NMR structural studies of the ionizing radiation adduct 7-hydro-8-oxodeoxyguanosine (8-oxo-7H-dG) opposite deoxyadenosine in a DNA duplex. 8-Oxo-7H-dG(syn).dA(anti) alignment at lesion site. Biochemistry. 1991 Feb 5;30(5):1403–1412. doi: 10.1021/bi00219a034. [DOI] [PubMed] [Google Scholar]
  13. Kuchino Y., Mori F., Kasai H., Inoue H., Iwai S., Miura K., Ohtsuka E., Nishimura S. Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and at adjacent residues. Nature. 1987 May 7;327(6117):77–79. doi: 10.1038/327077a0. [DOI] [PubMed] [Google Scholar]
  14. Lin T. S., Cheng J. C., Ishiguro K., Sartorelli A. C. 8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells. J Med Chem. 1985 Sep;28(9):1194–1198. doi: 10.1021/jm00147a012. [DOI] [PubMed] [Google Scholar]
  15. 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]
  16. Oda Y., Uesugi S., Ikehara M., Nishimura S., Kawase Y., Ishikawa H., Inoue H., Ohtsuka E. NMR studies of a DNA containing 8-hydroxydeoxyguanosine. Nucleic Acids Res. 1991 Apr 11;19(7):1407–1412. doi: 10.1093/nar/19.7.1407. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Ogilvie K. K., Slotin L. 2',3'-carbonates of 8-hydroxypurine nucleosides. J Org Chem. 1971 Aug 27;36(17):2556–2558. doi: 10.1021/jo00816a042. [DOI] [PubMed] [Google Scholar]
  18. Pon R. T., Damha M. J., Ogilvie K. K. Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides. Nucleic Acids Res. 1985 Sep 25;13(18):6447–6465. doi: 10.1093/nar/13.18.6447. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Pon R. T., Usman N., Damha M. J., Ogilvie K. K. Prevention of guanine modification and chain cleavage during the solid phase synthesis of oligonucleotides using phosphoramidite derivatives. Nucleic Acids Res. 1986 Aug 26;14(16):6453–6470. doi: 10.1093/nar/14.16.6453. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Shibutani S., Takeshita M., Grollman A. P. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature. 1991 Jan 31;349(6308):431–434. doi: 10.1038/349431a0. [DOI] [PubMed] [Google Scholar]
  21. Sinha N. D., Biernat J., McManus J., Köster H. Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucleic Acids Res. 1984 Jun 11;12(11):4539–4557. doi: 10.1093/nar/12.11.4539. [DOI] [PMC free article] [PubMed] [Google Scholar]
  22. Uesugi S., Ikehara M. Carbon-13 magnetic resonance spectra of 8-substituted purine nucleosides. Characteristic shifts for the syn conformation. J Am Chem Soc. 1977 May 11;99(10):3250–3253. doi: 10.1021/ja00452a008. [DOI] [PubMed] [Google Scholar]
  23. Wood M. L., Dizdaroglu M., Gajewski E., Essigmann J. M. Mechanistic studies of ionizing radiation and oxidative mutagenesis: genetic effects of a single 8-hydroxyguanine (7-hydro-8-oxoguanine) residue inserted at a unique site in a viral genome. Biochemistry. 1990 Jul 31;29(30):7024–7032. doi: 10.1021/bi00482a011. [DOI] [PubMed] [Google Scholar]

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