Collect. Czech. Chem. Commun. 1981, 46, 947-956

Synthesis and pharmacological properties of [2-p-fluorophenylalanine]deamino-1-carba-oxytocin and its diastereoisomeric sulfoxides

Zdenko Procházka, Michal Lebl, Linda Servítová, Tomislav Barth and Karel Jošt

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


Systematic build-up of the peptide chain in solution led to [2-p-fluorophenylalanine]deamino-1-carba-oxytocin which after purification by countercurrent distribution was obtained in the form of diastereoisomeric sulfoxides. The sulfoxides were separated by chromatography and reduced with hydrogen bromide and acetone to the corresponding sulfide. Uterotonic and galactogogic activity of all compounds was determined; the diastereoisomeric sulfoxides differed markedly in these activities.