Abstract
In this article, we address the presence of the prekinamycin quinone methide using the techniques of spectral global fitting and the 13C-labeling of the reactive centre. Two-electron reduction of a prekinamycin affords a long-lived quinone methide species that was characterised spectrally. A correlation was made between the calculated ΔE (kcal/mol) values for quinone methide tautomerisation and cytostatic activity to support the postulate that the quinone methide plays a role in prekinamycin biological activity. We also prepared a stable quinone methide of prekinamycin and studied its solution chemistry directly.
Original language | English (US) |
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Pages (from-to) | 2140-2154 |
Number of pages | 15 |
Journal | Organic and Biomolecular Chemistry |
Volume | 7 |
Issue number | 10 |
DOIs | |
State | Published - 2009 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry