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  • Title: A model study of fecapentaenes: mutagens of bacterial origin with alkylating properties.
    Author: Gupta I, Suzuki K, Bruce RW, Krepinsky JJ, Yates P.
    Journal: Science; 1984 Aug 03; 225(4661):521-3. PubMed ID: 6377497.
    Abstract:
    Fecapentaene-14 and -12 are directly acting mutagens that do not require metabolic activation. Their unusual structure suggests a possible mechanism of action. A carbocation that is formed by the addition of an electrophilic species (such as a proton) to the enol ether is most probably the reactive species. A series of model enol ethers with conjugated systems of various lengths was prepared, and a correlation between mutagenicity and increasing reactivity of derived carbocations was found. The glycerol moiety does not play a crucial role in the overall reactivity of the fecapentaenes.
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