Monoamine oxidase-catalyzed oxidation of endo,endo-2-amino-6-[(Z)-2'-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate.
An 11-step synthesis of endo,endo-2-amino-6-[(E)-2'-phenyl]ethenylbicyclo[2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed.
Wang
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Department of Chemistry, Northwestern University, Evanston, IL 60208-3113, USA.
Silverman
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D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D002417:Cattle; D005609:Free Radicals / Q000378:metabolism; D006536:Heptanes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D007536:Isomerism; D007700:Kinetics; D008099:Liver / Q000201:enzymology; D008956:Models, Chemical; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D008995:Monoamine Oxidase / Q000378:metabolism*; D009636:Norbornanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D013379:Substrate Specificity
C418207:2-amino-6-(2'-phenyl)ethenylbicyclo(2.2.1)heptane; D000588:Amines; D001643:Bridged Bicyclo Compounds; D005609:Free Radicals; D006536:Heptanes; D015335:Molecular Probes; D009636:Norbornanes; D008995:Monoamine Oxidase