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. 1991 Nov 11;19(21):5815–5820. doi: 10.1093/nar/19.21.5815

Incorporation by chemical synthesis and characterization of deoxyribosylformylamine into DNA.

A Guy 1, A M Duplaa 1, J Ulrich 1, R Téoule 1
PMCID: PMC329032  PMID: 1945871

Abstract

2-deoxyribosylformylamine is a major oxidative DNA damage type which occurs upon the action of ionizing radiation on DNA. The protected 2-deoxyribosylformylamine phosphoramidite was synthesized and used in conjunction with previously reported alkali labile base protected phosphoramidites ('PAC phosphoramidites') for the preparation of oligodeoxyribonucleotides containing this lesion. Final deprotection of the oligonucleotides was performed under mild alkaline conditions to preserve the integrity of the fragile defect. The presence of formylamino deoxyribosyl residue was confirmed by FAB mass spectrometry sequencing. Oligonucleotides bearing deoxyribosyl formylamine were used as templates for studying in vitro replication. They direct the insertion of guanine or induce a deletion opposite the lesion.

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Selected References

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

  1. Bailly V., Verly W. G. Escherichia coli endonuclease III is not an endonuclease but a beta-elimination catalyst. Biochem J. 1987 Mar 1;242(2):565–572. doi: 10.1042/bj2420565. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Barone A. D., Tang J. Y., Caruthers M. H. In situ activation of bis-dialkylaminophosphines--a new method for synthesizing deoxyoligonucleotides on polymer supports. Nucleic Acids Res. 1984 May 25;12(10):4051–4061. doi: 10.1093/nar/12.10.4051. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Demple B., Linn S. DNA N-glycosylases and UV repair. Nature. 1980 Sep 18;287(5779):203–208. doi: 10.1038/287203a0. [DOI] [PubMed] [Google Scholar]
  4. Eadie J. S., Davidson D. S. Guanine modification during chemical DNA synthesis. Nucleic Acids Res. 1987 Oct 26;15(20):8333–8349. doi: 10.1093/nar/15.20.8333. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Grotjahn L., Frank R., Blöcker H. Ultrafast sequencing of oligodeoxyribonucleotides by FAB-mass spectrometry. Nucleic Acids Res. 1982 Aug 11;10(15):4671–4678. doi: 10.1093/nar/10.15.4671. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Guschlbauer W., Duplaa A. M., Guy A., Téoule R., Fazakerley G. V. Structure and in vitro replication of DNA templates containing 7,8-dihydro-8-oxoadenine. Nucleic Acids Res. 1991 Apr 25;19(8):1753–1758. doi: 10.1093/nar/19.8.1753. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Hevroni D., Livneh Z. Bypass and termination at apurinic sites during replication of single-stranded DNA in vitro: a model for apurinic site mutagenesis. Proc Natl Acad Sci U S A. 1988 Jul;85(14):5046–5050. doi: 10.1073/pnas.85.14.5046. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Ide H., Kow Y. W., Wallace S. S. Thymine glycols and urea residues in M13 DNA constitute replicative blocks in vitro. Nucleic Acids Res. 1985 Nov 25;13(22):8035–8052. doi: 10.1093/nar/13.22.8035. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Ide H., Melamede R. J., Wallace S. S. Synthesis of dihydrothymidine and thymidine glycol 5'-triphosphates and their ability to serve as substrates for Escherichia coli DNA polymerase I. Biochemistry. 1987 Feb 10;26(3):964–969. doi: 10.1021/bi00377a042. [DOI] [PubMed] [Google Scholar]
  10. Kow Y. W., Wallace S. S. Mechanism of action of Escherichia coli endonuclease III. Biochemistry. 1987 Dec 15;26(25):8200–8206. doi: 10.1021/bi00399a027. [DOI] [PubMed] [Google Scholar]
  11. Kunkel T. A., Schaaper R. M., Loeb L. A. Depurination-induced infidelity of deoxyribonucleic acid synthesis with purified deoxyribonucleic acid replication proteins in vitro. Biochemistry. 1983 May 10;22(10):2378–2384. doi: 10.1021/bi00279a012. [DOI] [PubMed] [Google Scholar]
  12. Maxam A. M., Gilbert W. Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 1980;65(1):499–560. doi: 10.1016/s0076-6879(80)65059-9. [DOI] [PubMed] [Google Scholar]
  13. Nielsen J., Dahl O. Improved synthesis of (Pri2 N)2POCH2CH2CN. Nucleic Acids Res. 1987 Apr 24;15(8):3626–3626. doi: 10.1093/nar/15.8.3626. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Pon R. T. An improved iodine/water oxidation reagent for automated oligonucleotide synthesis. Nucleic Acids Res. 1987 Sep 11;15(17):7203–7203. doi: 10.1093/nar/15.17.7203. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Randall S. K., Eritja R., Kaplan B. E., Petruska J., Goodman M. F. Nucleotide insertion kinetics opposite abasic lesions in DNA. J Biol Chem. 1987 May 15;262(14):6864–6870. [PubMed] [Google Scholar]
  16. Sagher D., Strauss B. Insertion of nucleotides opposite apurinic/apyrimidinic sites in deoxyribonucleic acid during in vitro synthesis: uniqueness of adenine nucleotides. Biochemistry. 1983 Sep 13;22(19):4518–4526. doi: 10.1021/bi00288a026. [DOI] [PubMed] [Google Scholar]
  17. Schulhof J. C., Molko D., Teoule R. The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groups. Nucleic Acids Res. 1987 Jan 26;15(2):397–416. doi: 10.1093/nar/15.2.397. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. 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]
  19. Takeshita M., Chang C. N., Johnson F., Will S., Grollman A. P. Oligodeoxynucleotides containing synthetic abasic sites. Model substrates for DNA polymerases and apurinic/apyrimidinic endonucleases. J Biol Chem. 1987 Jul 25;262(21):10171–10179. [PubMed] [Google Scholar]
  20. Teoule R., Bert C., Bonicel A. Thymine fragment damage retained in the DNA polynucleotide chain after gamma irradiation in aerated solutions. II. Radiat Res. 1977 Nov;72(2):190–200. [PubMed] [Google Scholar]
  21. Téoule R. Radiation-induced DNA damage and its repair. Int J Radiat Biol Relat Stud Phys Chem Med. 1987 Apr;51(4):573–589. doi: 10.1080/09553008414552111. [DOI] [PubMed] [Google Scholar]

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