Table of Contents
International Journal of Spectroscopy
Volume 2012, Article ID 847676, 8 pages
http://dx.doi.org/10.1155/2012/847676
Research Article

Gas Chromatography Electron Ionization Mass Spectral Analysis of Thio Analogues of Pyrimidine Bases: 5-Bromo-2,4-di-o-(m- and p-) chloro- (bromo-)benzylthiouracils and 6-methyluracils

Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

Received 14 July 2011; Accepted 30 September 2011

Academic Editor: Hans Riesen

Copyright © 2012 G. Bartkowiak et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. L. S. Goodman and A. Gilman, Eds., The Pharmacological Basis of Therapeutics, Macmillan, New York, NY, USA, 5th edition, 1975.
  2. W. Saenger, in Principles of Nucleic Acids Structure, Springer-Verlag: New York, Berlin, Heidelberg, Tokyo, 1984, Chapter 7.
  3. W. Saenger and D. Suck, “The relationship between hydrogen bonding and base stacking in crystalline 4-thiouridine derivatives,” European Journal of Biochemistry, vol. 32, no. 3, pp. 473–478, 1973. View at Google Scholar · View at Scopus
  4. U. Thewalt and C. E. Bugg, “Effects of sulfur substituents on base stacking and hydrogen bonding. The crystal structure of 6-thioguanosine monohydrate,” Journal of the American Chemical Society, vol. 94, no. 25, pp. 8892–8898, 1972. View at Publisher · View at Google Scholar
  5. A. G. Lezius and K. H. Scheit, “Enzymatic synthesis of DNA with 4-thio-thymidine triphosphate as substitute for dTTP,” European Journal of Biochemistry, vol. 3, no. 1, pp. 85–94, 1967. View at Google Scholar · View at Scopus
  6. E. M. Gottschalk, E. Kopp, and A. G. Lezius, “A synthetic DNA with unusual base-pairing,” European Journal of Biochemistry, vol. 24, no. 1, pp. 168–182, 1971. View at Google Scholar · View at Scopus
  7. K. H. Scheit and E. Gaertner, “Die Polymerization von 4-Thiouridin-5'-diphosphat und 4-thiothymidin-5'-diphosphat durch Polynucleotidphosphorylase aus Micrococcus lysodeikticus,” Biochimica et Biophysica Acta, vol. 182, no. 1, 1969. View at Google Scholar
  8. E. Freese, “The specific mutagenic effect of base analogues on phage T4,” Journal of Molecular Biology, vol. 1, no. 2, pp. 87–105, 1959. View at Publisher · View at Google Scholar
  9. E. Freese, “The difference between spontaneous and base-analogue induced mutations of phage T4,” Proceedings of the National Academy of Sciences of the United States of America, vol. 45, no. 4, pp. 622–633, 1959. View at Google Scholar
  10. S. Y. Wang, “Pyrimidine bimolecular photoproducts,” in Photochemistry and Photobiology of Nucleic Acids, vol. 1, pp. 295–326, Academic Press, New York, NY, USA, 1976. View at Google Scholar
  11. M. Imaizumi, F. Kano, and S. Sakata, “Novel uracil derivatives: newly synthesized centrally acting agents,” Chemical and Pharmaceutical Bulletin, vol. 40, no. 7, pp. 1808–1813, 1992. View at Google Scholar · View at Scopus
  12. I. W. Althaus, K.-C. Chou, R. J. Lemay et al., “The benzylthio-pyrimidine U-31,355, a potent inhibitor of HIV-1 reverse transcriptase,” Biochemical Pharmacology, vol. 51, no. 6, pp. 743–750, 1996. View at Publisher · View at Google Scholar · View at Scopus
  13. R. A. Nugent, S. T. Schlachter, M. J. Murphy et al., “Pyrimidine thioethers: a novel class of HIV-1 reverse transcriptase inhibitors with activity against BHAP-resistant HIV,” Journal of Medicinal Chemistry, vol. 41, no. 20, pp. 3793–3803, 1998. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  14. P. Crain, T. Hasizume, and J. A. McCloskey, in Biological Mass Spectrometry, ed. by A. L. Burlingame and J. A. McCloskey, 671–692, Elsevier, Amsterdam [1990].
  15. K. Schram, “Mass spectrometry of nucleic acid components,” in Biological Application of Mass Spectrometry, C. H. Suelter and J. T. Watson, Eds., pp. 203–288, John Wiley, New York, NY, USA, 1990. View at Publisher · View at Google Scholar
  16. J. A. McCloskey, in Mass Spectrometry in the Health and Life Sciences, ed. by A. L. Burlingame and N. Castagnoli Jr., Elsevier Amsterdam [1985].
  17. J. A. McCloskey, in Mass Spectrometry in Biomedical Research, ed. by S. J. Gaskell, Wiley, New York [1986].
  18. J. Garin, J. Orduna, J. M. Royo, A.-M. Le Quere, and H. Muller, “Differentiation of isomeric sulfur heterocycles by electron ionization mass spectrometry: 1,4-dithiins, 1,4-dithiafulvenes nad their analogues tetrathianaphtalenes, tetrathiafulvalenes and tetrathiapentalenes,” Rapid Communications in Mass Spectrometry, vol. 17, no. 6, pp. 547–552, 2003. View at Publisher · View at Google Scholar · View at PubMed
  19. V. Ovcharenko, M. Rzadkowska, T. Tkaczynski, D. Matosiuk, and K. Pihlaja, “Electron impact mass spectra of substituted 1-aryl-2-arylsulphonylamino-δ2-imidzazolines,” Rapid Communications in Mass Spectrometry, vol. 11, no. 9, pp. 1043–1045, 1997. View at Publisher · View at Google Scholar · View at Scopus
  20. E. Wyrzykiewicz and Z. Nowakowska, “Mass spectrometry of thio analogues of pyrimidine bases: correlation of the intensities of the M+• and selected fragment ions of o-(m- and p-)substituted benzylthiouracils,” Journal of Mass Spectrometry, vol. 30, no. 2, pp. 269–274, 1995. View at Publisher · View at Google Scholar · View at Scopus
  21. E. Wyrzykiewicz and G. Bartkowiak, “Mass spectrometry of thio analogues of pyrimidine bases: Correlation of the intensities of the M+• and the [M–SH]+ ions of 2-alkylthiouracils,” Organic Mass Spectrometry, vol. 27, no. 12, pp. 1377–1380, 1992. View at Publisher · View at Google Scholar
  22. G. Bartkowiak, “Differentiation of 2-alkylthioorotic acids, methyl and ethyl 2-alkylthioorotates and hydrazides of 2-alkylthioorotic acids by using electron ionization mass spectra,” European Journal of Mass Spectrometry, vol. 14, no. 1, pp. 27–35, 2008. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  23. J. Wybieralska, “Electron impact induced mass spectral study of 2- and 4- ethoxycarbonylalkylthio-5-bromo-6-methyluracils,” Rapid Communications in Mass Spectrometry, vol. 14, no. 12, pp. 1074–1076, 2000. View at Publisher · View at Google Scholar · View at Scopus
  24. G. Bartkowiak, E. Wyrzykiewicz, G. Schroeder, A. Walkowiak, A. Szponar, and I. Pawlak, “Thio analogues of pyrimidine bases: Syntheses and spectral study of new potentially biologically active 2,4-di-ortho-(meta- and para-) bromo- (chloro and nitro)-benzylthio-5-bromouracils (and 6-methyluracils),” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 185, no. 7, pp. 1429–1436, 2010. View at Publisher · View at Google Scholar · View at Scopus
  25. F. W. McLafferty and F. Turecek, Interpretation of Mass Spectra, University Science Books, Mill Valley, Calif, USA, 4th edition, 1993.
  26. G. Bartkowiak, “Electron ionization induced mass spectral study of 2-alkylthio- and 4-alkykthio-5-bromouracils,” Rapid Communications in Mass Spectrometry, vol. 19, no. 9, pp. 1207–1212, 2005. View at Publisher · View at Google Scholar · View at PubMed · View at Scopus
  27. E. Wyrzykiewicz and G. Bartkowiak, “EIMS and C-13 NMR study of new ortho (meta and para) substituted derivatives of 2-benzylthioorotic acids,” Polish Journal of Chemistry, vol. 69, no. 4, p. 566, 1995. View at Google Scholar
  28. A. S. Plaziak, H. Wójtowicz-Rajchel, and K. Golankiewicz, “Mass spectrometry of 2,4-dialkoxy-5-bromopyrimidines,” Polish Journal of Chemistry, vol. 72, no. 4, pp. 719–724, 1998. View at Google Scholar · View at Scopus