Sammelbandbeitrag

Erschienen in: High Performance Computing in Science and Engineering ’99. Transactions of the High Performance Computing Center Stuttgart (HLRS) 1999

Herausgeberliste: Krause, E; Jäger, W

Jahr der Veröffentlichung: 2000

Seiten: 194-211

ISBN: 978-3-642-64084-1

eISBN: 978-3-642-59686-5

DOI Link: https://doi.org/10.1007/978-3-642-59686-5_17

Abstract: 

The ring-closure reactions of the enediyne and enyne-allene moieties of the natural antitumor antibiotics neocarzinostatin (1), calicheamicin (4), and dynemicin (5) are held responsible for the DNA-cleavage abilities of these potent pharmacophors. Neocarzinostatin, first isolated from Streptomyces carzinostaticus in 1961 [1], consists of the key chromophore 1 (Fig. 1.1) bound to a 113-amino acid apoprotein. [2,3] The enediyne moiety of 1 is activated by a thiol nucleophile, rearranges to enyne-cumulene 2, and cyclizes to the highly reactive biradical 3 (Fig. 1.1), a reaction akin to the Myers-Saito cyclization. [4] Since 1 binds to the minor groove of DNA, [5–;7] 3 is able to abstract hydrogens from adenine or thymine moieties [8] leading to cell damage. While calicheamicin 4 and dynemicin 5 (Fig. 1.1) undergo Bergman cyclizations to give rise to 1,4-didehydrobenzene biradicals, the neocarzinostatin chromophore 1 reacts differently.

Harvard-Zitierstil: Prall, M. and Schreiner, P. (2000) High Level Quantum-Chemical Computations on the Cyclizations of Enyne Allenes, in Krause, E. and Jäger, W. (eds.) High Performance Computing in Science and Engineering ’99. Transactions of the High Performance Computing Center Stuttgart (HLRS) 1999. Heidelberg: Springer-Verlag, pp. 194-211. https://doi.org/10.1007/978-3-642-59686-5_17

APA-Zitierstil: Prall, M., & Schreiner, P. (2000). High Level Quantum-Chemical Computations on the Cyclizations of Enyne Allenes. In Krause, E., & Jäger, W. (Eds.), High Performance Computing in Science and Engineering ’99. Transactions of the High Performance Computing Center Stuttgart (HLRS) 1999 (pp. 194-211). Springer-Verlag. https://doi.org/10.1007/978-3-642-59686-5_17