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N-methylputrescine oxidation during cocaine biosynthesis: study of prochiral methylene hydrogen discrimination using
T R Hoye1, J A Bjorklund, D O Koltun
1Department of Chemistry, University of Minnesota, Minneapolis 55455, USA. hoye@chem.umn.edu
Organic Letters
|May 18, 2000
Abstract:
[structure: see text] The stereoselectivity of N-methylputrescine (3) oxidation to pyrrolinium ion 4 in Erythroxylum coca during cocaine (1) biosynthesis was studied. The remote isotope method was used to advantage. Each enantiomer of 4-monodeuterated N-methylputrescine served as a precursor for plant feeding. To facilitate mass-spectrometric analysis of products, a 2H3 13C-methyl group was also incorporated into the 4-deuterio-N-methylputrescines. Oxidative deamination of N-methylputrescine was found to be stereoselective; the pro-S hydrogen atom is removed with 6-10:1 selectivity.