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Reductive activation of mitomycin A by thiols
1Department of Chemistry, Hunter College, City University of New York, New York, New York 10021, USA.
Organic Letters
|September 1, 2001
Abstract:
[reaction: see text]. 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.