Cysteine adds to lipid hydroperoxide
- 1 August 1977
- Vol. 12 (8) , 655-660
- https://doi.org/10.1007/bf02533760
Abstract
Cysteine reacts with linoleic acid hydroperoxide to yield several products, some of which were identified as fatty acid-cysteine adducts. The addition was catalyzed by ferric chloride (10−5 M) by initiating free radical reactions. When isomerically pure 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid and cysteine were reacted in 80% ethanol under N2, the major adducts were 9-S-cysteine-13-hydroxy-10-ethoxy-trans-11-octadecenoic acid (I) and 9-S-cysteine-10,13-dihydroxy-trans-11-octadecenoic acid (II). When the reaction included both isomers of the hydroperoxide (13-and 9-hydroperoxide) and air, an adduct of 9-oxononanoic acid and cysteine also was isolated. Additional experiments gave information about possible mechanisms of I and II formation.This publication has 17 references indexed in Scilit:
- Free radical reactions of peroxidizing lipids with amino acids and proteins: An ESR studyLipids, 1976
- Addition ofN‐acetylcysteine to linoleic acid hydroperoxideLipids, 1976
- Homolytic decomposition of linoleic acid hydroperoxide: Identification of fatty acid productsLipids, 1974
- Interacitons of the Autoxidized Products of Linoleic Acid with Enzyme ProteinsAgricultural and Biological Chemistry, 1973
- Inactivation of Enzymes by Linoleic Acid Hydroperoxides and Linoleic AcidAgricultural and Biological Chemistry, 1970
- Inactivation of ribonuclease and other enzymes by peroxidizing lipids and by malonaldehydeBiochemistry, 1969
- Reaction of cysteine and methionine with malonaldehydeJournal of Oil & Fat Industries, 1969
- Damage to proteins, enzymes, and amino acids by peroxidizing lipidsArchives of Biochemistry and Biophysics, 1966
- The destruction of —SH groups of proteins and amino acids by peroxides of unsaturated fatty acidsBiochemical Pharmacology, 1962
- Effect of unsaturated fatty acids and their peroxides on enzymesBiochemical Pharmacology, 1961