Collect. Czech. Chem. Commun. 1979, 44, 3128-3132

Vasopressin analogs modified in position 3. Influence of changes of configuration

Milan Zaorala, Danuta Konopinskab, Ivan Bláhaa, Viktor Krchňáka, Jana Škopkováa and Alena Machovác

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Instytut Chemii Universytetu Wroclawskiego, Wroclaw
c Research Institute for Pharmacy and Biochemistry, 190 00 Prague 9


The condensation of p-toluenesulfonyl-S-benzylcysteinyl-tyrosine azide with D-phenylalanine methyl ester afforded p-toluenesulfonyl-S-benzylcysteinyl-tyrosyl-D-phenylalanine methyl ester which was subsequently converted into the hydrazide and azide and coupled with glutaminyl-asparaginyl-S-benzylcysteine methyl ester. p-Toluenesulfonyl-S-benzylcysteinyl-tyrosyl-D-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteine methyl ester was condensed via the hydrazide and azide with prolyl-Nγ-p-toluenesulfonyl-αγ-diaminobutyryl-glycine amide. After removal of the protecting groups, closure of the disulfide bridge and purification, [3-D-phenylalanine, 8-α,γ-diaminobutyric acid]vasopressin was obtained which shows an appreciable antidiuretic effect of distinct specifity.