Transimination reaction between pyridoxal‐5′‐phosphate schiff bases with dodecylamine and amino acids

Some transimination processes were studied using an intermolecular model formed by pyridoxal‐5′ ‐phosphate (PLP) an amino acid and dodecylamine (DOD) in an aqueous medium. All the kinetic constants for the reversible reaction were determined. The results show that in these cases transimination proceeds through an addition‐elimination by forming a diamine geminal intermediate. Equilibria are always shifted to dodecylamine‐PLP Schiff base formation. Differences between the stability of this Schiff base and the ϵ‐aminocaproic Schiff base cannot be explained only on the basis of the different nucleophicities of amine groups and therefore differences in the imine double bond environment must be taken into account to explain this behaviour.