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. Author manuscript; available in PMC: 2020 May 20.
Published in final edited form as: Chem Res Toxicol. 2019 Mar 18;32(5):796–807. doi: 10.1021/acs.chemrestox.9b00013

Figure 4.

Figure 4.

Mechanism of asparagine deamidation and its reversal. Peptide backbone nitrogen attacks the side chain amide, releasing ammonia to form a succinimide ring. Upon hydrolysis, either aspartate or isoaspartate are formed. PIMT methylates the resulting carboxylate, forming an ester that is spontaneously hydrolyzed by intramolecular attack from backbone amide nitrogen to reform the succinimide ring. Successive rounds of this mechanism may be required to fully repair deamidation.