Reductive Activation of Mitomycin A by Thiols

Autor: Paz, M. M., Tomasz, M.
Zdroj: Organic Letters; September 2001, Vol. 3 Issue: 18 p2789-2792, 4p
Abstrakt: Mitomycin C is unchanged upon exposure to thiols under physiological conditions. Its more toxic variant, mitomycin A (MA), undergoes elimination of methanol to give a variety of mitosene derivatives, diagnostic of its activation to a reactive electrophile. Evidence is presented for a novel reductive mechanism, characterized by the transient addition of a thiol to the quinone of MA, followed by intramolecular electron transfer, leading to reduced quinone and oxidized thiol.
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