A model study of fecapentaenes: mutagens of bacterial origin with alkylating properties

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Science  03 Aug 1984:
Vol. 225, Issue 4661, pp. 521-523
DOI: 10.1126/science.6377497


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.