Collect. Czech. Chem. Commun. 1980, 45, 2865-2871

Synthesis and some pharmacological properties of [7-glycine, 8-ornithine]vasopressin and two of its analogues

Michal Lebl, Tomislav Barth, Jana Škopková and Karel Jošt

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Protected peptides were prepared by fragment condensation according to the scheme 6 + 3 or 9 + 3, which, after the removal of the protecting groups by sodium in liquid ammonia and oxidative cyclization, afforded [7-glycine,8-ornithine]vasopressin, [7-glycine,8-ornithine]deaminovasopressin, and Nα-glycyl-glycyl-glycyl[7-glycine,8-ornithine]vasopressin. All the analogues had very low intrinsic vasopressin-like activities; the analogue with hormonogen nature had a depressor effect and inhibited the pressor action of lysine-vasopressin.