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Additional resources for Protein Formulation and Delivery, Second Edition (Drugs and the Pharmaceutical Sciences)

Example text

McNally PTR 09/24/07 Chapter 02 16 Bummer Some of the general rules for peptides may also show higher levels of dependence on primary sequence. 3. For X = His, Ser, Ala, Arg, and Leu, deamidation rates were essentially constant and approximately seven times slower than the ValSer-Asn-Gly-Val standard peptide. Of special interest to the investigators was the observation of no difference in deamidation rates between those amino acids with and without β-branching (such as valine for glycine). This is in direct contrast to the findings of Robinson and Rudd (24) of 10-fold differences in deamidation for valine substitution for glycine in Gly-X-Asn-Ala-Gly, shown earlier.

In production lots, removal of water to attain such low levels of residual moisture is quite expensive. McNally PTR 32 09/24/07 Chapter 02 Bummer Proteins and Peptides in Polymers Care must be exercised when attempting to encapsulate pharmaceutical proteins or peptides within a polymer matrix. Cross-linking of methylated dextrans by addition of potassium peroxyodisulfate resulted in significant oxidation of methionine residues in interleukin-2 (171). Addition of tetramethylethylenediamine minimized, but did not eliminate, the oxidation of sensitive amino acids.

A variety of products are produced, including the amino acids aspartic acid and Asn (76,120). From the standpoint of pharmaceutical formulations, recent evidence suggests that the oxidation products of ascorbic acid (a frequently employed antioxidant) may be potent photosensitizing agents, enhancing histidine oxidation in proteins. Ortwerth et al. (119) reported 1O2 concentrations in the millimolar range and H2O2 in the micromolar range after one hour of irradiation with ultraviolet light in the presence of dehydroascorbate and diketogulonic acid (by-products of ascorbic acid oxidation).

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