Synthesis, antidiuretic and pressor activities of [arginine4]arginine-vasopressin and two related analogues

Using well-established solid-phase techniques, three new analogues of arginine-vasopressin (AVP) were synthesized. In these the glutamine residue in position 4 was replaced with an additional arginine. The new analogues were: [Arginine4]arginine-vasopressin ([Arg4]AVP), [2-thiopropionic acid1,arginine4]arginine-vasopressin (d[Arg4]AVP) and [1-thiocyclohexaneacetic acid1,arginine4]arginine-vasopressin (d(CH2)5[Arg4]AVP). [Arg4]AVP showed about the same antidiuretic activity as AVP but had only about 40% of its pressor activity. Unexpectedly, deamination caused a drop in the antidiuretic activity to about 50%. d(CH2)5[Arg4]AVP had practically negligible antidiuretic and low pressor effects.     

Synthesis and study of the rate of aminolysis of O-(acylaminoacyl)oximes of formylpyridines and pyridyl methyl ketones

A number of O-(benzyloxycarbonylglycyl) derivatives of alkyl-, phenyl-, and pyridyl-substituted oximes were synthesized, and their chemical properties and reactivities under aminolysis conditions were studied. The principal factor that determines the reactivities of the investigated compounds during the formation of a peptide bond is the presence of a weakly acidic catalyst; the different reactivities of the compounds under the same conditions are due to the influence of the electron-acceptor effects of the substituents attached to the carbon atom of the oxime group.The authors thank the Polish Academy of Sciences for financial support (state subsidy MR 1.12.1.6.1.5).Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1336–1339, October, 1977.