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Na
Na
in the deamidation of an asparagine residue under physiological conditions, the side chain is attacked by the nitrogen atom of the following peptide group (in black at top right of figure), forming an asymmetric succinimide intermediate (in red). the asymmetry of the intermediate results in two products of its hydrolysis, either aspartic acid (in black at left) or isoaspartic acid, which is a beta amino acid (in green at bottom right). however there is a concern that aspartic acid can be isomerized after deamidation. the deamidation of a glutamine residue may proceed via the same mechanism but at a much slower rate since formation of the six-member-ring glutarimide intermediate is less favoured than the succinimide intermediate for asparagine. in general, deamidation can be eliminated by proteolysis at an acidic ph or at a slightly basic ph (4.5 and 8.0, respectively) using the endoprotease, glu-c.
deamidation