Facile N-oxygenation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine by the flavin-containing monooxygenase. A convenient synthesis of tritiated (methyl-/sup 3/H)-4-phenyl-2,3-dihydropyridinium species
A rapid, efficient procedure useful for the radiosynthesis of (Me-/sup 3/H)-MPDP+ ((methyl-/sup 3/H)-4-phenyl-2,3-dihydropyridinium species) is described. Hog liver microsomes or the highly purified flavin-containing monooxygenase from hog liver quantitatively biotransforms (Me-/sup 3/H)-MPTP to its corresponding radiolabeled N-oxide. For the small-scale synthesis required for radiolabeling procedures, this enzymatic process is superior to H/sub 2/O/sub 2/-mediated N-oxygenation of MPTP. In the presence of 0.5 mM NADPH, 4.5 mM n-octylamine, and 2 microCi (Me-/sup 3/H)-MPTP, the only product detected in extracts from incubations performed with hog liver microsomes or purified hog liver flavin-containing monooxygenase is (Me-/sup 3/H)-MPTP N-oxide. (Me-/sup 3/H)-MPTP N-oxide is almost completely converted to (Me-/sup 3/H)-MPDP+ by the action of trifluoroacetic anhydride. This procedure has the advantage of using a commercially available tritiated starting material, efficient transformations, and easily accomplished purification to afford a rapid synthesis of (Me-/sup 3/H)-MPDP+.
- Research Organization:
- Univ. of California, San Francisco (USA)
- OSTI ID:
- 6974251
- Journal Information:
- J. Med. Chem.; (United States), Vol. 31:6
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
OXYGENASES
ENZYME ACTIVITY
PYRIDINES
METABOLISM
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MICROSOMES
NADP
PYRIDINIUM COMPOUNDS
SWINE
TRACER TECHNIQUES
TRITIUM COMPOUNDS
AMINES
AMMONIUM COMPOUNDS
ANIMALS
AZINES
BODY
CELL CONSTITUENTS
COENZYMES
DIGESTIVE SYSTEM
DOMESTIC ANIMALS
ENZYMES
GLANDS
HETEROCYCLIC COMPOUNDS
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
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ORGANIC NITROGEN COMPOUNDS
ORGANOIDS
ORGANS
OXIDOREDUCTASES
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550501* - Metabolism- Tracer Techniques