Monoamine Oxidase-Catalyzed Oxidative Rearrangement of trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane |
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| Authors: | Lu Xingliang Yang Shengtian Silverman Richard B. |
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| Affiliation: | Department of Chemistry and Department of Biochemistry, Molecular Biology, and Cell Biology, Northwestern University, Evanston, Illinois 60208-3113. |
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| Abstract: | trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane (3) was synthesized in three steps from (Z)-beta-methoxystyrene and ethyl diazoacetate. Compound 3 was shown to be a substrate and inactivator of mitochondrial beef liver monoamine oxidase (MAO) with a partition ratio of 1428. MAO-catalyzed oxidation of 3 produces one major metabolite, isolated and identified by GCOSY, GHMQC, and GHMBC NMR techniques to be trans,trans-2-methoxy-3-phenyl-1-N-[(3-phenyl-N-pyrrolyl)methyl]cyclopropane (7). A mechanism, supported by a model reaction, is proposed for the formation of this metabolite. |
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