Collect. Czech. Chem. Commun. 1982, 47, 689-701

Analogues of neurohypophysial hormones, containing tert-leucine: Synthesis and properties

Michal Lebl, Jan Pospíšek, Jan Hlaváček, Tomislav Barth, Petr Maloň, Linda Servítová, Karel Hauzer and Karel Jošt

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


Analogues of oxytocin, deamino-oxytocin and deamino-vasopressin, containing tert-leucine in position 8, were prepared by fragment condensation in solution. Stepwise synthesis in solution afforded analogues of 1-carba- and 6-carba-deamino-oxytocin with tert-leucine in position 2. [8-Tert-leucine]oxytocin proved to be the most interesting of this series; it exhibits a relatively high and specific galactogogic activity and is cleaved with chymotrypsin by an order of magnitude more slowly than oxytocin.