The Modification of Lysine

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Abstract
The chemical modification of lysine residues in proteins is based upon the ability of the ∊-amino group of this residue to react as a nucleophile. Under normal reaction conditions, lysyl residues are the second strongest nucleophiles in a protein molecule; cysteine is the most reactive nucleophile. However, for lysine to function optimally as a nucleophile, the proton usually bound to lysyl residues at physiological pH must be removed. This is shown in Figure 1. The protonated form is essentially unreactive. The pKa of an “average” lysyl residue in a protein is 10 (see Table 2 in Chapter 6). The majority of modification reactions are performed at pH 8.0 to 9.0.

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