N-Methylputrescine Oxidation during Cocaine Biosynthesis:  Study of Prochiral Methylene Hydrogen Discrimination Using the Remote Isotope Method

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 facilit...

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Bibliographic Details
Published in:Organic letters 2000-01, Vol.2 (1), p.3-5
Main Authors: Hoye, Thomas R, Bjorklund, Jeffrey A, Koltun, Dmitry O, Renner, Matthew K
Format: Article
Language:English
Subjects:
Carbon Isotopes
Coca - metabolism
Cocaine - biosynthesis
Deuterium
Mass Spectrometry
Molecular Structure
Oxidation-Reduction
Plants, Medicinal
Putrescine - analogs & derivatives
Putrescine - metabolism
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990940s