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. 1994 May 10;91(10):4534-8.
doi: 10.1073/pnas.91.10.4534.

Spontaneous generation of a biradical species of neocarzinostatin chromophore: role in DNA bulge-specific cleavage

O D Hensens  1 , D H Chin, A Stassinopoulos, D L Zink, L S Kappen, I H Goldberg
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Spontaneous generation of a biradical species of neocarzinostatin chromophore: role in DNA bulge-specific cleavage

O D Hensens et al. Proc Natl Acad Sci U S A. .

Abstract

Detailed structure determination of the major and minor base-catalyzed degradation products of the chromophore of the enediyne anticancer antibiotic neocarzinostatin in the absence of DNA demonstrates that the enolate Michael addition reaction leading to a spirolactone cumulene intermediate is a spontaneous, stereoselective process. The implications of these findings for the mechanism of the thiol-independent, site-specific cleavage by the so-generated radical species of the drug at a DNA bulge are described.

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References

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