Synthesis of vasoactive intestinal peptide (VIP) via the mixed anhydride method.
Porcine VIP was synthesized from three segments. The segments, VIP(1-6), VIP(7-13), and VIP(14-28), were synthesized via the Repetitive Excess Mixed Anhydride (REMA) method. The low solubility of the C-terminal segment was greatly improved by a temporary substitution of Asn28 by a beta-t-butyl aspartic acid ester. The segments VIP(1-6) and VIP(7-13) were purified by HPLC and coupled via the mixed anhydride method. The product was purified by gel filtration. VIP was synthesized from VIP(1-13) and VIP(14-28) by the same procedure. After deprotection, Met17-sulfoxide reduction, and purification by ion-exchange chromatography, the product was found to have the expected amino acid composition and biological potency. A HPLC purified sample was compared with several commercial preparations of varying purity.
D000595:Amino Acid Sequence; D000812:Anhydrides; D000818:Animals; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D010446:Peptide Fragments / Q000138:chemical synthesis; D013552:Swine; D014660:Vasoactive Intestinal Peptide / Q000138:chemical synthesis*
D000812:Anhydrides; D007202:Indicators and Reagents; D010446:Peptide Fragments; D014660:Vasoactive Intestinal Peptide