Abstract
We have investigated the reaction of N-( carbobenzyloxy)- l-histidine with E-2-octenal and analyzed the products to identify the components that produce a significant loss of histidine residues in the reaction of E-2-octenal and proteins. When the mixture of N-( carbobenzyloxy)- l-histidine and E-2-octenal was incubated at pH 7.0 and 37°C for 24 h, E-2-octenoic acid and isomeric forms of N-( carbobenzyloxy)-1-(3)-(1′-(formylmethyl)hexyl)- l-histidine were obtained. Althought other possibilities are not excluded, it is suggested that the modification of histidine residues in proteins by E-2-octenal involves a Michael-type addition of the imidazole nitrogen atom of histidine to the α,β-unsaturated bond of E-2-octenal.
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