Lysine-derived fluorophores formed by autoxidation of linoleic acid.
To obtain an insight into fluorophores formed in proteins during lipid peroxidation, a lysine residue analogue (N(alpha)-hippuryllysine) was exposed to autoxidation of linoleic acid catalyzed by iron(III)-EDTA and L-ascorbic acid. The reaction predominantly produced two fluorescent products, N,N'-bis[5-(N-benzoylglycylamino)-5-carboxypentyl]-2-hydroxy-2-pentyl-3-imino-l,2-dihydropyrrole (II) and N,N'-bis[5-(N-benzoylglycylamino)-5-carboxypentyl]-2-hydroxy-2-(7-carboxyheptyl)-3-imino-1,2-dihydropyrolle (I).
Itakura
Koichi
K
Faculty of Education, Aichi University of Education, 448-8542, Kariya, Japan. kitakura@auecc.aichi-edu.ac.jp
Uchida
Koji
K
D001205:Ascorbic Acid / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D004492:Edetic Acid / Q000737:chemistry / Q000494:pharmacology; D005290:Ferric Compounds / Q000737:chemistry / Q000494:pharmacology; D005452:Fluoresceins / Q000737:chemistry* / Q000378:metabolism; D007097:Imines / Q000737:chemistry* / Q000378:metabolism; D019787:Linoleic Acid / Q000737:chemistry* / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry* / Q000378:metabolism; D011506:Proteins / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry* / Q000378:metabolism; D013997:Time Factors
D005290:Ferric Compounds; D005452:Fluoresceins; D007097:Imines; C480568:N,N'-bis(5-(N-benzoylglycylamino)-5-carboxypentyl)-2-hydroxy-2-(7-carboxyheptyl)-3-imino-1,2-dihydropyrolle; C480567:N,N'-bis(5-(N-benzoylglycylamino)-5-carboxypentyl)-2-hydroxy-2-pentyl-3-imino-l,2-dihydropyrrole; D011506:Proteins; D011758:Pyrroles; D004492:Edetic Acid; D019787:Linoleic Acid; D008239:Lysine; C019179:Fe(III)-EDTA; D001205:Ascorbic Acid