title: Side-reactions in peptide synthesis. 2. Formation of by-products in the large-scale synthesis of THF-gamma 2 by solution synthesis.
abstract: The impurities which formed in the large-scale synthesis of THF-gamma 2, an immunomodulatory peptide of formula H-Leu-Glu-Asp-Gly-Pro-Lys-Phe-Leu-OH, were identified by a combination of analytical methods, and their structure confirmed by synthesis. Most impurities originated from side-reactions involving the aspartyl residue (cyclization, beta-aspartyl formation and cleavage). Based on this knowledge, modifications were introduced into the work up and the purification procedure which resulted in a very pure final product (> 99% by RP-HPLC).
authors.affiliation: Farmitalia Carlo Erba S.r.l., Research and Development, Nerviana (MI), Italy.
authors.forename: R
authors.initials: R
authors.lastname: Forino
authors.forename: M
authors.initials: M
authors.lastname: Galantino
authors.forename: F
authors.initials: F
authors.lastname: Ciprandi
authors.forename: L
authors.initials: L
authors.lastname: Baumer
authors.forename: E
authors.initials: E
authors.lastname: Arlandini
authors.forename: R
authors.initials: R
authors.lastname: De Castiglione
mesh_terms: D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D006863:Hydrogen-Ion Concentration; D008969:Molecular Sequence Data; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000302:isolation & purification; D013951:Thymus Hormones / Q000138:chemical synthesis / Q000302:isolation & purification
chemical_list: D009842:Oligopeptides; D013951:Thymus Hormones; C064563:thymic humoral factor gamma 2