IDEAS home Printed from https://ideas.repec.org/h/spr/sprchp/978-3-642-59686-5_17.html
   My bibliography  Save this book chapter

High Level Quantum-Chemical Computations on the Cyclizations of Enyne Allenes

In: High Performance Computing in Science and Engineering ’99

Author

Listed:
  • Matthias Prall

    (Georg-August-University, Institute of Organic Chemistry)

  • Peter R. Schreiner

    (Georg-August-University, Institute of Organic Chemistry)

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.

Suggested Citation

  • Matthias Prall & Peter R. Schreiner, 2000. "High Level Quantum-Chemical Computations on the Cyclizations of Enyne Allenes," Springer Books, in: Egon Krause & Willi Jäger (ed.), High Performance Computing in Science and Engineering ’99, pages 194-211, Springer.
    • Handle: RePEc:spr:sprchp:978-3-642-59686-5_17
    DOI: 10.1007/978-3-642-59686-5_17
    as

    Download full text from publisher

    To our knowledge, this item is not available for download. To find whether it is available, there are three options:
    1. Check below whether another version of this item is available online.
    2. Check on the provider's web page whether it is in fact available.
    3. Perform a
    for a similarly titled item that would be available.

    More about this item

    Keywords

    ;
    ;
    ;
    ;
    ;

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:spr:sprchp:978-3-642-59686-5_17. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    We have no bibliographic references for this item. You can help adding them by using this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.springer.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.