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. 1983 Aug 11;11(15):5093–5102. doi: 10.1093/nar/11.15.5093

Site-specific modification of the lactose operator with acetylaminofluorene.

G Stöhrer, J A Osband, G Alvarado-Urbina
PMCID: PMC326239  PMID: 6878040

Abstract

We have synthesized the tetradecamer GAGCXGATAACAAG containing a part of the sequence of the lactose operator. A guanine base in the sequence is replaced by the adduct of the carcinogen 2-acetylaminofluorene with guanine. Under the standard conditions of de-protection, the fluorene moiety is lost, leaving behind a guanine oxidation product. New conditions of de-protection have been developed which allow the isolation of an oligonucleotide containing the adduct of 2-aminofluorene with guanine. The presence of the aminofluorene adduct greatly increases retention on reverse phase chromatography and produces a unique pattern of sequencing bands.

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Selected References

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

  1. Alvarado-Urbina G., Sathe G. M., Liu W. C., Gillen M. F., Duck P. D., Bender R., Ogilvie K. K. Automated synthesis of gene fragments. Science. 1981 Oct 16;214(4518):270–274. doi: 10.1126/science.6169150. [DOI] [PubMed] [Google Scholar]
  2. BURTON K. A study of the conditions and mechanism of the diphenylamine reaction for the colorimetric estimation of deoxyribonucleic acid. Biochem J. 1956 Feb;62(2):315–323. doi: 10.1042/bj0620315. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Bahl C. P., Wu R., Stawinsky J., Narang S. A. Minimal length of the lactose operator sequence for the specific recognition by the lactose repressor. Proc Natl Acad Sci U S A. 1977 Mar;74(3):966–970. doi: 10.1073/pnas.74.3.966. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Büchi H., Khorana H. G. CV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxyribonucleotide corresponding to the nucleotide sequence 31 to 50. J Mol Biol. 1972 Dec 28;72(2):251–288. doi: 10.1016/0022-2836(72)90148-9. [DOI] [PubMed] [Google Scholar]
  5. CRAMER J. W., MILLER J. A., MILLER E. C. N-Hydroxylation: A new metabolic reaction observed in the rat with the carcinogen 2-acetylaminofluorene. J Biol Chem. 1960 Mar;235:885–888. [PubMed] [Google Scholar]
  6. Evans F. E., Miller D. W., Beland F. A. Sensitivity of the conformation of deoxyguanosine to binding at the C-8 position by N-acetylated and unacetylated 2-aminofluorene. Carcinogenesis. 1980;1(11):955–959. doi: 10.1093/carcin/1.11.955. [DOI] [PubMed] [Google Scholar]
  7. Fuchs R. P., Daune M. P. Dynamic structure of DNA modified with the carcinogen N-acetoxy-n-2-acetylaminofluorene. Biochemistry. 1974 Oct 8;13(21):4435–4440. doi: 10.1021/bi00718a028. [DOI] [PubMed] [Google Scholar]
  8. King C. M., Traub N. R., Cardona R. A., Howard R. B. Comparative adduct formation of 4-aminobiphenyl and 2-aminofluorene derivatives with macromolecules of isolated liver parenchymal cells. Cancer Res. 1976 Jul;36(7 Pt 1):2374–2381. [PubMed] [Google Scholar]
  9. Kriek E. Carcinogenesis by aromatic amines. Biochim Biophys Acta. 1974 Sep 9;355(2):177–203. doi: 10.1016/0304-419x(74)90003-1. [DOI] [PubMed] [Google Scholar]
  10. Kriek E., Miller J. A., Juhl U., Miller E. C. 8-(N-2-fluorenylacetamido)guanosine, an arylamidation reaction product of guanosine and the carcinogen N-acetoxy-N-2-fluorenylacetamide in neutral solution. Biochemistry. 1967 Jan;6(1):177–182. doi: 10.1021/bi00853a029. [DOI] [PubMed] [Google Scholar]
  11. 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]
  12. Miller E. C. Some current perspectives on chemical carcinogenesis in humans and experimental animals: Presidential Address. Cancer Res. 1978 Jun;38(6):1479–1496. [PubMed] [Google Scholar]
  13. Miller J. A. Carcinogenesis by chemicals: an overview--G. H. A. Clowes memorial lecture. Cancer Res. 1970 Mar;30(3):559–576. [PubMed] [Google Scholar]
  14. Morin N. R., Zeldin P. E., Kubinski Z. O., Bhattacharya P. K., Kubinski H. Macromolecular complexes produced by chemical carcinogens and ultraviolet radiation. Cancer Res. 1977 Oct;37(10):3802–3814. [PubMed] [Google Scholar]
  15. Rubin C. M., Schmid C. W. Pyrimidine-specific chemical reactions useful for DNA sequencing. Nucleic Acids Res. 1980 Oct 24;8(20):4613–4619. doi: 10.1093/nar/8.20.4613. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Santella R. M., Kriek E., Grunberger D. Circular dichroism and proton magnetic resonance studies of dApdG modified with 2-aminofluorene and 2-acetylaminofluorene. Carcinogenesis. 1980;1(11):897–902. doi: 10.1093/carcin/1.11.897. [DOI] [PubMed] [Google Scholar]
  17. Tang M., Lieberman M. W., King C. M. uvr Genes function differently in repair of acetylaminofluorene and aminofluorene DNA adducts. Nature. 1982 Oct 14;299(5884):646–648. doi: 10.1038/299646a0. [DOI] [PubMed] [Google Scholar]
  18. Tarpley W. G., Miller J. A., Miller E. C. Rapid release of carcinogen-guanine adducts from DNA after reaction with N-acetoxy-2-acetylaminofluorene or N-benzoyloxy-N-methyl-4-aminoazobenzene. Carcinogenesis. 1982;3(1):81–88. doi: 10.1093/carcin/3.1.81. [DOI] [PubMed] [Google Scholar]
  19. Visser A., Westra J. G. Partial persistency of 2-aminofluorene and N-acetyl-2-aminofluorene in rat liver DNA. Carcinogenesis. 1981;2(8):737–740. doi: 10.1093/carcin/2.8.737. [DOI] [PubMed] [Google Scholar]
  20. Yamasaki H., Pulkrabek P., Grunberger D., Weinstein I. B. Differential excision from DNA of the C-8 and N2 guanosine adducts of N-acetyl-2-aminofluorene by single strand-specific endonucleases. Cancer Res. 1977 Oct;37(10):3756–3760. [PubMed] [Google Scholar]

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