Addition of N-acetylcysteine to linoleic acid hydroperoxide
- PMID: 1250075
- DOI: 10.1007/BF02532662
Addition of N-acetylcysteine to linoleic acid hydroperoxide
Abstract
Catalyzed by 10(-5)M ionic iron in 80% ethanol, N-acetylcysteine added to linoleic acid hydroperoxide, forming a thiobond. Reaction of a specific isomer of hydroperoxide, 13-hydroperoxy-trans-11, cis-9-octadecadienoic acid, and N-acetylcysteine, forms a number of products, of which two were identified as addition compounds. One addition product was 9-S-(N-acetylcysteine)-13-hydroxy-10-ethoxy-trans-11-octadecenoic acid, and the other was 9-S-(N-acetylcysteine)-10, 13-dihydroxy-trans-11-octadecenoic acid.
Similar articles
-
Cysteine adds to liquid hydroperoxide.Lipids. 1977 Aug;12(8):655-60. doi: 10.1007/BF02533760. Lipids. 1977. PMID: 895415
-
Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase.J Lipid Res. 1970 Jul;11(4):311-21. J Lipid Res. 1970. PMID: 5459662
-
Degradation of linoleic acid hydroperoxides by a cysteine . FeCl3 catalyst as a model for similar biochemical reactions. II. Specificity in formation of fatty acid epoxides.Biochim Biophys Acta. 1981 Jul 24;665(1):113-24. doi: 10.1016/0005-2760(81)90239-3. Biochim Biophys Acta. 1981. PMID: 7284409
-
Conversion of linoleic acid hydroperoxide to hydroxy, keto, epoxyhydroxy, and trihydroxy fatty acids by hematin.J Biol Chem. 1985 May 10;260(9):5351-7. J Biol Chem. 1985. PMID: 3988758
-
Positional specificity of gamma-ketol formation from linoleic acid hydroperoxides by a corn germ enzyme.Lipids. 1975 Oct;10(10):602-8. doi: 10.1007/BF02532724. Lipids. 1975. PMID: 1186445
Cited by
-
Lipid oxidation: biologic effects and antioxidants--a review.Lipids. 1980 Jun;15(6):485-95. doi: 10.1007/BF02534079. Lipids. 1980. PMID: 7401947
-
Prevention of doxorubicin cardiac toxicity in the mouse by N-acetylcysteine.J Clin Invest. 1981 Oct;68(4):1053-64. doi: 10.1172/jci110328. J Clin Invest. 1981. PMID: 7287901 Free PMC article.
-
Indication of reduced doxorubicin-induced cardiac toxicity by additional treatment with antioxidative substances.Experientia. 1983 Jan 15;39(1):62-4. doi: 10.1007/BF01960629. Experientia. 1983. PMID: 6825779
-
Reactive Sterol Electrophiles: Mechanisms of Formation and Reactions with Proteins and Amino Acid Nucleophiles.Chemistry (Basel). 2020 Jun;2(2):390-417. doi: 10.3390/chemistry2020025. Epub 2020 May 6. Chemistry (Basel). 2020. PMID: 35372835 Free PMC article.
-
Cysteine adds to liquid hydroperoxide.Lipids. 1977 Aug;12(8):655-60. doi: 10.1007/BF02533760. Lipids. 1977. PMID: 895415
References
MeSH terms
Substances
LinkOut - more resources
Full Text Sources