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The Scientific World Journal
Volume 2012 (2012), Article ID 526289, 7 pages
http://dx.doi.org/10.1100/2012/526289
Research Article

Tautomerism in 11-Hydroxyaklavinone: A DFT Study

Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey

Received 5 October 2011; Accepted 22 December 2011

Academic Editor: Raúl Rivas

Copyright © 2012 Lemi Türker. 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. F. Arcamone, Doxorubicine Anticancer Antibiotics, Academic Press, New York, NY, USA, 1981.
  2. F. M. Hauser and D. Mal, “Regiospecific total syntheses of (±)-aklavinone and (±)-ε-pyrromycinone from a common synthon,” Journal of the American Chemical Society, vol. 106, no. 4, pp. 1098–1104, 1984. View at Scopus
  3. T. Oki, Y. Matsuzawa, and A. Yoshimoto, “New antitumor antibiotics, aclacinomycins A and B,” The Journal of Antibiotics, vol. 28, pp. 830–834, 1975.
  4. T. Oki, N. Shibamoto, Y. Matsuzawa et al., “Production of nineteen anthracyclic compounds by Streptomyces galilaeus MA144-M1,” The Journal of Antibiotics, vol. 30, pp. 683–687, 1977.
  5. T. Oki, I. Kitamura, A. Yoshimoto, et al., “Antitumor anthracycline antibiotics, aclacinomycin A and analogs. I. Taxonomy, production, isolation and physicochemical properties,” The Journal of Antibiotics, vol. 32, pp. 791–800, 1979.
  6. H. Tanaka, T. Yoshioka, Y. Shimauchi, Y. Matsuzawa, T. Oki, and T. Inui, “Chemical modification of anthracycline antibiotics. I. Demethoxycarbonylation, 10-epimerization and 4-O-methylation of aclacinomycin A,” Journal of Antibiotics, vol. 33, no. 11, pp. 1323–1330, 1980. View at Scopus
  7. H. Yamaki, H. Suzuki, T. Nishimura, and N. Tanaka, “Mechanism of action of aclacinomycin A. I. The effect on macromolecular synthesis,” Journal of Antibiotics, vol. 31, no. 11, pp. 1149–1154, 1978. View at Scopus
  8. A. S. Kerde and J. P. Rizzi, “A stereospecific total synthesis of aklavinone,” Journal of the American Chemical Society, vol. 103, no. 14, pp. 4247–4248, 1981. View at Scopus
  9. B. A. Pearlman, J. M. McNamara, I. Hasan, S. Hatakeyama, H. Sekizaki, and Y. Kishi, “Practical total synthesis of (±)-aklavinone and total synthesis of aklavin,” Journal of the American Chemical Society, vol. 103, no. 14, pp. 4248–4251, 1981. View at Scopus
  10. A. S. Kende and J. P. Rizzi, “A stereospecific total synthesis of aklavinone,” Journal of the American Chemical Society, vol. 103, no. 14, pp. 4247–4248, 1981. View at Scopus
  11. T. T. Li and Y. L. Wu, “Facile regio- and stereoselective total synthesis of racemic aklavinone,” Journal of the American Chemical Society, vol. 103, no. 23, pp. 7007–7009, 1981. View at Scopus
  12. D. W. Jones and C. J. Lock, “Synthesis of ( ± )-aklavinone and ( ± )-auramycinone via electron-deficient o-quinonoid pyrones,” Journal of the Chemical Society, Perkin Transactions 1, no. 21, pp. 2747–2755, 1995. View at Scopus
  13. D. L. Kleyer and T. H. Koch, “Mechanistic investigation of reduction of daunomycin and 7-deoxydaunomycinone with bi(3,5,5-trimethyl-2-oxomorpholin-3-yl),” Journal of the American Chemical Society, vol. 106, no. 8, pp. 2380–2387, 1984. View at Scopus
  14. M. Kodama, A. Misako, N. Chikayoshi, O. Toshikazu, and M. Yasue, “An electron spin resonance study on the free radicals produced from aclacinomycin A and its derivatives: analysis of hyperfine structure of the spectra by means of molecular orbital method,” Cancer Biochemistry Biophysics, vol. 6, pp. 243–247, 1983.
  15. T. W. G. Solomons and C. B. Fryhle, Organic Chemistry, Wiley, New York, NY, USA, 2004.
  16. D. L. Kleyer, G. Gaudiano, and T. H. Koch, “Spectroscopic and kinetic evidence for the tautomer of 7-deoxyalklavinone as an intermediate in the reductive coupling of aclacinomycin A,” Journal of the American Chemical Society, vol. 106, no. 4, pp. 1105–1109, 1984. View at Scopus
  17. N. S. Egerov, Antibiotics, a Scientific Approach, Mir, Moscow, Russia, 1985.
  18. J. J. P. Stewart, “Optimization of parameters for semi empirical methods I method,” J. Comput. Chem, vol. 10, pp. 209–220, 1989.
  19. J. J. P. Stewart, “Optimization of parameters for semi empirical methods II,” Journal of Chemical Theory and Computation, vol. 10, pp. 221–264, 1989.
  20. A. R. Leach , Molecular Modeling, Longman, Essex, Conn, USA, 1997.
  21. W. Kohn and L. J. Sham, “Self-consistent equations including exchange and correlation effects,” Physical Review, vol. 140, no. 4A, pp. A1133–A1138, 1965. View at Publisher · View at Google Scholar · View at Scopus
  22. R. G.Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, London, UK, 1989.
  23. Spartan, Molecular Modeling in Physical Chemistry, Wavefuction, Irvine, Calif, USA, 2005.
  24. D. C.Young , Computational Chemistry, Wiley-Interscience, NY, USA, 2001.
  25. A. D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behavior,” Physical Review A, vol. 38, no. 6, pp. 3098–3100, 1988. View at Publisher · View at Google Scholar · View at Scopus
  26. S. H. Vosko, L. Vilk, and M. Nusair, “Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis,” Canadian Journal of Physics, vol. 58, pp. 1200–1211, 1980.
  27. C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Physical Review B, vol. 37, no. 2, pp. 785–789, 1988. View at Publisher · View at Google Scholar · View at Scopus
  28. SPARTAN, Wavefunction Inc., Irvine, Calif, USA, 2006.
  29. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH, Weinheim, Germany, 2004.
  30. C. J. Cramer, Essentials of Computational Chemistry, Wiley, Chichester, UK, 2004.