PMID: 11916399Mar 28, 2002Paper

Formation and structure of a novel enediyne-RNA base covalent adduct

Journal of the American Chemical Society
Zhi-Hong JiangI H Goldberg

Abstract

The structure of an unusual covalent adduct formed by thiol-activated neocarzinostatin chromophore (NCS-chrom) and a RNA-DNA hybrid having an overhang of four unpaired residues at the 3'-end of the RNA strand has been elucidated by MS and NMR spectroscopic analyses. Unlike previously characterized adducts formed by NCS-chrom on the sugar residue of the DNA target, this adduct has been found to be on one of the uracil bases in the RNA overhang. Covalent linkage is between C-6 of the post-activated NCS-chrom and C-5 of the uracil. A novel mechanism involving adduction of the NCS-chrom C-6 radical, generated by 2-mercaptoethanol activation, to C-5 of the uracil at the U9 position of the RNA 11-mer, oxidation by dioxygen, reduction by the thiol, and subsequent dehydration is proposed for adduct formation.

References

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Sep 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·M TomaszG L Verdine
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Jan 16, 1999·Biochemistry·L S Kappen, I H Goldberg

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Citations

Jan 15, 2015·Chemical Research in Toxicology·Martin Dracínský, Radek Pohl
Jan 17, 2020·The Journal of Organic Chemistry·Chang-Xue GuMing-Hua Xu
Jul 11, 2002·Chemical Reviews·Scott E Wolkenberg, Dale L Boger

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