N-methylputrescine oxidation during cocaine biosynthesis: Study of prochiral methylene hydrogen discrimination using the remote isotope method

Thomas R. Hoye, Jeffrey A. Bjorklund, Dmitry O. Koltun, Matthew K. Renner

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

(formula presented) 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 2H313C-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.

Original languageEnglish (US)
Pages (from-to)3-5
Number of pages3
JournalOrganic Letters
Volume2
Issue number1
DOIs
StatePublished - Jan 2000

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