Spin trapping of 13C-labeled p-benzynes generated by Masamune–Bergman cyclization of bicyclic nine-membered enediynes

Usuki, Toyonobu and Mita, Takashi and Lear, Martin J. and Das, Parthasarathi and Yoshimura, Fumihiko and Inoue, Masayuki and Hirama, Masahiro and Akiyama, Kimio and Tero-Kubota, Shozo (2004) Spin trapping of 13C-labeled p-benzynes generated by Masamune–Bergman cyclization of bicyclic nine-membered enediynes. Angewandte Chemie International Edition, 43 (39). pp. 5249-5253. ISSN 1433-7851

Full content URL: http://dx.doi.org/10.1002/anie.200454133

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Abstract

Our understanding of the chemistry and biology of the enediyne class of antitumor antibiotics is still developing and
faces further challenges. The cleavage of double-stranded DNA through hydrogen abstraction by enediyne-derived
radicals is a generally well-accepted mechanism. However, the mechanisms of several unexpected and complex
cytotoxic effects of enediynes,such as RNA and protein damage or the generation of p-quinone species, have yet to be fully elucidated. Despite several carefully crafted experimental and theoretical studies on simplified systems,the
behavior of the major chemical perpetrators of such cytotoxicity, namely the biradical intermediates formed by natural enediynes, remains more a matter of conjecture than a point of fact.

Keywords:Natural enediynes, p-Benzynes, Isotope labelling, Mechanism
Subjects:F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Chemistry
ID Code:17122
Deposited On:16 Apr 2015 13:42

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