Chemistry of the Hydrated Electron in Oxygen-Free Solutions of Amino Acids, Peptides, and Related Compounds

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Abstract
In extending previous studies on the radiation-induced deamination of the simpler [alpha]-amino acids in oxygen-free solution, it was found that reductive deamination by the hydrated electron, eeq, is not confined to the free amino acid configuration. The dipeptides, tripeptides, and other derivatives of glycine, for example, are found to react with eq (essentially quantitatively) to cleave the N[long dash]C bond of the primary amino group. Radiolysis studies of variously substituted amino compounds in solutions containing 2nd solutes which are specific scavengers of H, OH in the one case and of eaq, in the other indicates that reductive deamination by eaq requires an unsaturated function at the carbon position a t o the amino group. It is suggested that eaq adds to this function and that N[long dash]C cleavage then ensues. Observed correlations between rates of reaction of eaq and pK of the amino group are in accord with this formulation. Velocity constants for reaction of eaq with amino acids and derivatives in both acidic and neutral solution were obtained by the method of competition kinetics.

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