HPLC and NMR investigation of the serum amine oxidase catalyzed oxidation of polyamines.
In the presence of amine oxidases polyamines arrest cell proliferation owing to the generation of hydrogen peroxide and amino aldehydes. In this investigation the bovine serum amine oxidase catalyzed oxidation of polyamines has been studied by HPLC analysis of dansylated reaction products with or without NaBH4 reduction and by NMR spectroscopy of the reaction products and 3-aminopropanal was found to be a major reaction product. These findings were further substantiated by analysis of the reaction products by ion-exchange chromatography and by analysis of the products formed by oxidation of polyamines by the cofactor of Cu amine oxidases, 6-hydroxydopa. 3-Aminopropanal is unstable and can give rise to acrolein by beta-elimination.
Houen
G
G
Institute of Biochemical Genetics, Copenhagen, Denmark.
Bock
K
K
Jensen
A L
AL
D000171:Acrolein / Q000378:metabolism; D000447:Aldehydes / Q000378:metabolism; D006631:Amine Oxidase (Copper-Containing); D000818:Animals; D001894:Borohydrides; D002384:Catalysis; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D005312:Fetal Blood / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D000587:Oxidoreductases Acting on CH-NH Group Donors / Q000097:blood*; D011073:Polyamines / Q000378:metabolism*; D011437:Propylamines / Q000378:metabolism; D011700:Putrescine / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013095:Spermidine / Q000378:metabolism; D013096:Spermine / Q000378:metabolism
D000447:Aldehydes; D001894:Borohydrides; D011073:Polyamines; D011437:Propylamines; D013096:Spermine; D000171:Acrolein; C025364:sodium borohydride; D006631:Amine Oxidase (Copper-Containing); D000587:Oxidoreductases Acting on CH-NH Group Donors; C050862:3-aminopropionaldehyde; D013095:Spermidine; D011700:Putrescine