Collect. Czech. Chem. Commun. 1979, 44, 1642-1644

Effect of methylation of the hydroxyl group of tyrosine in [1-β-mercaptopropionic acid, 8-D-arginine]vasopressin on its biological effects

Viktor Krchňák and Milan Zaoral

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


Using the method of solid-phase synthesis, S-benzyl-β-mercaptopropionyl-O-methyltyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteinyl-prolyl-NG-p-toluenesulfonyl-D-arginyl-glycine amide (I) was prepared which after removal of the protecting groups, oxidation, and purification afforded [1-β-mercaptopropionic acid, 2-O-methyltyrosine, 8-D-arginine]vasopressin (II). II shows a low antidiuretic effect, c. 10 I.U./mg. It is without effect on rat uterus in vitro and on the blood pressure of rat in vitro.