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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.

Abstract

The antharquinone-based chromophore of 11-hydroxyaklavinone is present in the structure of an anticancer agent, daunomycin. On the other hand, aklavinone is the parent aglycone of certain anthracycline antibiotics that possess anti-cancer activity too. The structures of aklavinone and its 11-hydroxy derivative have many –OH groups, and two keto groups which may take place in certain tautomeric equilibria. Of these tautomeric forms, presently the one involving the anthraquinone based tautomers of 11-hydroxyaklavinone has been investigated quantum chemically in the framework of the density functional theory at the levels of RB3LYP/6-31G(d) and RB3LYP/6-31G(d,p).