“The Reaction of an Autoxidized Lipid With Proteins”, 1965-09 (; similar):
Evidence is presented which indicates that an interaction occurs between proteins and an autoxidizing unsaturated lipid. Using a model system approach, it has been established that two purified proteins (gelatin and insulin) are chemically modified in the presence of an autoxidizing lipid, methyl linoleate.
The insulin-methyl linoleate interaction has been studied chromatographically after acid and alkaline hydrolysis, and also by using the Sanger end group analysis method. The data indicate that lipid intermediates react with theε-amino group of lysine, and also with phenylalanine and glycine, the N-terminal amino groups of insulin.
Hydrogen fluoride solubility and enzyme hydrolysis determinations indicate that the autoxidation products of methyl linoleate interact with protein to produce new chemical entities through cross-linking.