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

Zhi Hong JIANG, Geum Sook Hwang, Zhen Xi, Irving H. Goldberg*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3216-3217
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number13
DOIs
Publication statusPublished - 3 Apr 2002

Scopus Subject Areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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