THE SYNTHESIS AND CHEMISTRY OF A SIMPLIFIED, FUNCTIONAL ANALOG OF NEOCARZINOSTATIN CHROMOPHORE - IDENTIFICATION OF AN INTRAMOLECULAR 1,5-HYDROGEN ATOM-TRANSFER RELEVANT TO THE MECHANISM AND CLEAVAGE SELECTIVITY OF DIYL-BASED DNA-CLEAVING AGENTS

[摘要] The synthesis and chemistry of a monocyclic analogue of neocarzinostatin chromophore are described. This analogue is activated through a Michael addition process and provides cycloaromatized products similar to those obtained in the activation of neocarzinostatin chromophore. Mechanistic studies on this analogue have led to the first identification of a diyl self-quenching pathway based on a 1,5-hydrogen atom transfer that provides a novel hypothesis about the relationship between thiol structure and DNA single and double strand cleavage selectivity for neocarzinostatin chromophore and diyl-based cleaving agents.

[发布日期] 1994-01-31