- About this Journal ·
- Abstracting and Indexing ·
- Advance Access ·
- Aims and Scope ·
- Annual Issues ·
- Article Processing Charges ·
- Articles in Press ·
- Author Guidelines ·
- Bibliographic Information ·
- Citations to this Journal ·
- Contact Information ·
- Editorial Board ·
- Editorial Workflow ·
- Free eTOC Alerts ·
- Publication Ethics ·
- Reviewers Acknowledgment ·
- Submit a Manuscript ·
- Subscription Information ·
- Table of Contents
The Scientific World Journal
Volume 2012 (2012), Article ID 526289, 7 pages
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.
- F. Arcamone, Doxorubicine Anticancer Antibiotics, Academic Press, New York, NY, USA, 1981.
- 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.
- T. Oki, Y. Matsuzawa, and A. Yoshimoto, “New antitumor antibiotics, aclacinomycins A and B,” The Journal of Antibiotics, vol. 28, pp. 830–834, 1975.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- T. W. G. Solomons and C. B. Fryhle, Organic Chemistry, Wiley, New York, NY, USA, 2004.
- 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.
- N. S. Egerov, Antibiotics, a Scientific Approach, Mir, Moscow, Russia, 1985.
- J. J. P. Stewart, “Optimization of parameters for semi empirical methods I method,” J. Comput. Chem, vol. 10, pp. 209–220, 1989.
- J. J. P. Stewart, “Optimization of parameters for semi empirical methods II,” Journal of Chemical Theory and Computation, vol. 10, pp. 221–264, 1989.
- A. R. Leach , Molecular Modeling, Longman, Essex, Conn, USA, 1997.
- W. Kohn and L. J. Sham, “Self-consistent equations including exchange and correlation effects,” Physical Review, vol. 140, no. 4A, pp. A1133–A1138, 1965.
- R. G.Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, London, UK, 1989.
- Spartan, Molecular Modeling in Physical Chemistry, Wavefuction, Irvine, Calif, USA, 2005.
- D. C.Young , Computational Chemistry, Wiley-Interscience, NY, USA, 2001.
- A. D. Becke, “Density-functional exchange-energy approximation with correct asymptotic behavior,” Physical Review A, vol. 38, no. 6, pp. 3098–3100, 1988.
- 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.
- 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.
- SPARTAN, Wavefunction Inc., Irvine, Calif, USA, 2006.
- C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH, Weinheim, Germany, 2004.
- C. J. Cramer, Essentials of Computational Chemistry, Wiley, Chichester, UK, 2004.