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Reaction of histidine with methyl linoleate: Characterization of the histidine degradation products
Author(s) -
Yong Samuel H.,
Karel Marcus
Publication year - 1978
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02669929
Subject(s) - histidine , chemistry , ninhydrin , imidazole , reactivity (psychology) , hydrolysis , aldehyde , moiety , organic chemistry , amino acid , biochemistry , catalysis , medicine , alternative medicine , pathology
Efforts have been made to characterize the products that result from interactions between L‐histidine (free base) and peroxidizing methyl linoleate (ML) in a model system consisting of reactants dispersed on a filter paper. Imidazole lactic acid and imidazole acetic acid are identified as breakdown products when histidine is incubated with ML, methyl linoleate hydroperoxide (MLHPO), or n‐hexanal over a period of 3 weeks. Two other reaction products are found to give back histidine upon acid hydrolysis. These products are though to be Schiff's base compounds which result from the condensation of the histidyl α‐amino group and carbonyl groups of reactive aldehydes formed during ML peroxidation. Most of the detectable reaction products have the imidazole moiety intact indicating the high relative reactivity of the functional groups, especially the amino group, associated with the α‐carbon. Such high reactivity provides an explanation for the low concentrations of ninhydrin‐positive free amino compounds that are, at best, barely detectable on thin layer chromatography.