CLEAVAGE OF THE IMIDAZOLE RING IN HISTIDYL RESIDUE ANALOGUES REACTED WITH PEROXIDIZING LIPIDS
- 1 March 1979
- journal article
- research article
- Published by Wiley in Journal of Food Science
- Vol. 44 (2) , 568-574
- https://doi.org/10.1111/j.1365-2621.1979.tb03838.x
Abstract
Degradative reactions initiated by peroxidizing lipids on the histidyl imidazole side‐chain were studied by reacting the histidyl residue analogues N‐benzoylhistidine and hippurylhistidyl‐leucine with methyl linoleate in a low‐moisture model system resembling the structure of freeze‐dried foods. We found that, after incubation at 51‐57°C and 75% relative humidity for 3 wk, the imidazole side‐chain was cleaved by peroxidizing methyl linoleate to yield asparagyl and aspartyl side‐chains along with other compounds at lower concentrations. The degradation of the histidyl imidazole ring (pKa= 6.0–6.5) increased significantly at pH ≥ 7, indicating that the free base form was the labile species.This publication has 32 references indexed in Scilit:
- Photooxidation of Human Serum Albumin and Its Complex with BilirubinEuropean Journal of Biochemistry, 1977
- Changes in lysozyme due to reactions with peroxidizing methyl linoleate in a dehydrated model systemJournal of Agricultural and Food Chemistry, 1976
- Nonenzymic BrowningZeitschrift für Lebensmittel-Untersuchung und Forschung, 1975
- Specific interactions of linoleic acid hydroperoxides and their secondary degraded products with enzyme proteinsJournal of Agricultural and Food Chemistry, 1975
- Subunit structure and photooxidation of yeast imidazoleglycerolphosphate dehydrataseBiochemistry, 1974
- Electron spin resonance study of the reaction of hydroxyl radicals with pyrrole, imidazole, and related compoundsThe Journal of Physical Chemistry, 1973
- Loss of methionine in casein during storage with autoxidizing methyl linoleateJournal of Agricultural and Food Chemistry, 1969
- Antioxidant Properties of Methionine EstersNature, 1968
- Photolysis of L-HistidineNature, 1965