Spectroscopic study of the Schiff bases of dodecylamine with pyridoxal 5′-phosphate and 5′-deoxypyridoxal. A model for the Schiff bases of pyridoxal 5′-phosphate in biological systems

Abstract

We recorded the absorption spectra of the Schiff bases of pyridoxal 5′-phosphate (PLP) and 5′-deoxypyridoxal (DPL) with dodecylamine (DOD) at different pH values. By applying deconvolution techniques to the spectra and analysing their different components we found that the above-mentioned Schiff bases in aqueous solutions of pH 7 adopted a conformation in which the pyridine ring is embedded in a very hydrophobic medium from which water is virtually completely excluded. This conformation in the same as that adopted by PLP when it acts as coenzyme for some enzymes such as glycogen phosphorylase. The experimental results obtained also show such a conformation to be highly favoured but sensitive to the protonation of the pyridine nitrogen, which makes the aromatic ring more readily accessible to the solvent.