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Species variability in the stereoselective N ‐oxidation of pargyline
Author(s) -
Hadley Mark R.,
Švajdlenka Emil,
Damani Lyaquatali A.,
Oldham Harriet G.,
Tribe Jeanette,
Camilleri Patrick,
Hutt Andrew J.
Publication year - 1994
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530060209
Subject(s) - chemistry , pargyline , enantiomer , metabolite , microsome , monooxygenase , stereospecificity , stereoselectivity , flavin containing monooxygenase , monoamine oxidase , high performance liquid chromatography , stereochemistry , enzyme , chromatography , cytochrome p450 , biochemistry , catalysis
The monoamine oxidase inhibitor pargyline ( N ‐benzyl‐ N ‐methyl‐2‐propynylamine) is known to undergo extensive in vitro microsomal N ‐oxidation, thought to be mediated predominantly by the flavin‐containing monooxygenase (FMO) enzyme system. Formation of the pargyline N ‐oxide (PNO) metabolite creates a chiral nitrogen centre and thus asymmetric oxidation is possible. This study describes a reverse‐phase high‐performance liquid chromatographic (HPLC) method for the quantitation of PNO and a chiral‐phase HPLC method for the determination of the enantiomeric ratio of PNO. In vitro microsomal N ‐oxidation of pargyline was found to be highly steroselective in a number of species, with the (+)‐enantiomer being formed preferentially. This metabolic transformation was stereospecific when purified porcine hepatic FMO was used as the enzyme source. © 1994 Wiley‐Liss, Inc.
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