All amino acids have two ionizable functional groups: an α-amino group (average pKā of 9.4) and an α-carboxylic acid group (average pKā of 2.2). Histidine also has an ionizable side chain (R group) with a pKā of about 6.0. One of the possible ionization states of histidine is shown in the image.
At what pH would the structure be the predominant ionization state? Consider the ionization state of all three of the functional groups.
The protonated form of the R group of histidine is shown in the structure. The ratio of the charged (protonated) form to the deprotonated form depends on the pKā of the R group and the pH of the solution.
Select the pH values at which the charged form of the R group would predominate: