Chemical stability of insulin. 4. Mechanisms and kinetics of chemical transformations in pharmaceutical formulation.

@article{Brange1992ChemicalSO,
  title={Chemical stability of insulin. 4. Mechanisms and kinetics of chemical transformations in pharmaceutical formulation.},
  author={Jens Jorgen Veilgaard Brange},
  journal={Acta pharmaceutica Nordica},
  year={1992},
  volume={4 4},
  pages={
          209-22
        }
}
Insulin decomposes by a multitude of chemical reactions [1-3]. It deamidates at two different residues by entirely different mechanisms. In acid, deamidation at AsnA21 is intramolecularly catalyzed by the protonated C-terminal, whereas above pH 6 an intermediate imide formation at residue AsnB3 leads to isoAsp and Asp derivatives. The imide formation requires a large rotation around the alpha-carbon/peptide carbonyl carbon bond at B3, corresponding to a 10 A movement of the B-chain N-terminal… CONTINUE READING

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