Inactivation of monoamine oxidase by allylamine does not result in flavin attachment
(1-TH)Allylamine was synthesized by sodium boro(TH)hydride reduction of acrolein followed by direct conversion of the (1-TH)allyl alcohol to N-allylphthalimide with triphenylphosphine, diethylazodicarboxylate, and phthalimide. The protecting group was removed with hydrazine. Inactivation of beef liver mitochondrial monoamine oxidase with (1-TH)allylamine led to incorporation of 1-6 eq of inactivator/active site depending upon the length of incubation time. Inactivation and radioactivity incorporation coincided; however, after 1 eq of tritium was incorporated and 5% enzyme activity remained, additional radioactivity continued to become incorporated into the enzyme. The optical spectrum of the FAD coenzyme changed during inactivation from that of oxidized to reduced flavin. Following dialysis of the inactivated enzyme, the spectrum remained reduced, but denaturation in urea rapidly resulted in reoxidation of the flavin. Under these same denaturing conditions, 96% of the radioactivity associated with the enzyme remained bound, therefore indicating that allylamine attachment is not to the flavin coenzyme but rather to an active site amino acid residue. The adduct also was stable to base and, to a lesser degree, acid treatment. Although allylamine and N-cyclopropylbenzylamine appear to be oxidized by monoamine oxidase to give 3-(amino acid residue) propanal adducts, two different amino acids seem to be involved because of a difference in stability of the adducts. The mechanisms for inactivation of monoamine oxidase by allylamine and reactivation by benzylamine are discussed in relation to previously reported results.
- Research Organization:
- Northwestern Univ., Evanston, IL
- OSTI ID:
- 6182214
- Journal Information:
- J. Biol. Chem.; (United States), Journal Name: J. Biol. Chem.; (United States) Vol. 27; ISSN JBCHA
- Country of Publication:
- United States
- Language:
- English
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59 BASIC BIOLOGICAL SCIENCES
AMIDES
AMINES
AMINO ACIDS
ANIMALS
BIOCHEMICAL REACTION KINETICS
BIOLOGICAL EFFECTS
BODY
CARBONIC ACID DERIVATIVES
CARBOXYLIC ACIDS
CATTLE
CELL CONSTITUENTS
COENZYMES
DIGESTIVE SYSTEM
DOMESTIC ANIMALS
ENZYME ACTIVITY
ENZYME INHIBITORS
ENZYMES
GLANDS
ISOTOPE APPLICATIONS
KINETICS
LABELLED COMPOUNDS
LIVER
MAMMALS
MITOCHONDRIA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANOIDS
ORGANS
OXIDOREDUCTASES
REACTION KINETICS
RUMINANTS
TRACER TECHNIQUES
TRITIUM COMPOUNDS
UREA
VERTEBRATES