Collect. Czech. Chem. Commun. 1979, 44, 275-287

Synthesis of oxytocin analogues modified in the tripeptide side-chain by condensation of aminoterminal linear hexapeptide with the carboxyterminal tripeptide

Jan Hlaváček, Tomislav Barth, Karel Bláha and Karel Jošt

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


For the synthesis of oxytocin (Ia) analogues modified in the carboxyterminal part of the molecule, a method based on the condensation of protected aminoterminal hexapeptide with tripeptides by the action of dicyclohexylcarbodiimide and pentafluorophenol in the presence of 1-hydroxybenzotriazole was devised. Using this method [7-[U-13C]proline]oxytocin (Ib), des-9-glycine-oxytocin (Ic) and methyl ester of oxytocinoic acid ([9-glycine methyl ester]oxytocin) (Id) were prepared.