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

doi:10.1021/ol990940s

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

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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 language	English (US)
Pages (from-to)	3-5
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	1
DOIs	https://doi.org/10.1021/ol990940s
State	Published - Jan 2000

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

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.",

author = "Hoye, {Thomas R.} and Bjorklund, {Jeffrey A.} and Koltun, {Dmitry O.} and Renner, {Matthew K.}",

year = "2000",

month = jan,

doi = "10.1021/ol990940s",

language = "English (US)",

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journal = "Organic Letters",

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T1 - N-methylputrescine oxidation during cocaine biosynthesis

T2 - Study of prochiral methylene hydrogen discrimination using the remote isotope method

AU - Hoye, Thomas R.

AU - Bjorklund, Jeffrey A.

AU - Koltun, Dmitry O.

AU - Renner, Matthew K.

PY - 2000/1

Y1 - 2000/1

N2 - (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.

AB - (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.

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

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