Abstract

The classical mechanism for the nitrous acid deamination of primary aliphatic amines at low pH calls for formation of carbocation ion intermediates, which react further to yield primary and secondary alcohols and alkenes. More concerted mechanisms may also provide the same product distribution. To examine the reactions between proteins and environmental nitrite, we recently investigated the deamination of ε-amino groups of poly-L-lysine at low pH as a model system using ¹³C NMR to determine the structures of the two new amino acids generated by the deamination reaction. Although reactions of other amino acid side chains with nitrite have been studied, deamination of ε-amino groups has received little attention.

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