[1-β-Mercaptopropionic acid, 8-α,β-diaminopropionic acid]vasopressin and [1-β-mercaptopropionic acid, 8-D-α,β-diaminopropionic acid]vasopressin. Two lysine-vasopressin analogs with considerable antidiuretic effect

1979 ◽  
Vol 44 (7) ◽  
pp. 2161-2164 ◽  
Author(s):  
Viktor Krchňák ◽  
Milan Zaoral ◽  
Alena Machová
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Pressor Effect ◽  
Phase Synthesis ◽  
Mercaptopropionic Acid ◽  
Antidiuretic Effect ◽  
Lysine Vasopressin ◽  
Diaminopropionic Acid

Two lysine-vasopressin analogs, [1-β-mercaptopropionic acid, 8-α,β-diaminopropionic acid]vasopressin (IVa) and [1-β-mercaptopropionic acid, 8-D-α,β-diaminopropionic acid]vasopressin (IVb) were prepared by solid phase synthesis. IVa and IVb show a considerable antidiuretic effect (1 079 and 1 000 I.U./mg, resp.) and a low pressor effect (14.0 and 22.8 I.U./mg, resp.). The uterotonic effect of IVa is 0.9 I.U./mg and of IVb 1.72 I.U./mg.

Vasopressin and oxytocin analogs with interchanged sequence of amino acids in positions 7 and 8. synthesis and biological effects

1981 ◽  
Vol 46 (9) ◽  
pp. 2136-2139 ◽  
Author(s):  
Ivo Bláha ◽  
Viktor Krchňák ◽  
Milan Zaoral
Keyword(s):  
Amino Acids ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Effects ◽  
Free Flow ◽  
Protecting Groups ◽  
Pressor Effect ◽  
Phase Synthesis ◽  
Antidiuretic Effect

p-Toluenesulfonyl-S-benzylcysteinyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteinyl-NG-p-toluenesulfanylarginyl-prolyl-glycineamide (I) and S-benzylcysteinyl-tyrosyl-isoleucyl-glutaminyl-asparaginyl-S-benzylcysteinyl-leucyl-prolyl-glycine amide (III) were prepared by solid phase synthesis. After removal of the protecting groups, closure of the disulfide ring, and purification by continuous free-flow electrophoresis [arginine7, proline8]vasopressin (II) and [leucine7, proline8]oxytocin (IV) were obtained. The antidiuretic effect of II is markedly higher than its pressor effect; IV possesses c. 6% of the uterotonic and c. 10% of the galactogogous effect of oxytocin.

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

1979 ◽  
Vol 44 (5) ◽  
pp. 1642-1644 ◽  
Author(s):  
Viktor Krchňák ◽  
Milan Zaoral
Keyword(s):  
Arginine Vasopressin ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Effects ◽  
Hydroxyl Group ◽  
Rat Uterus ◽  
Phase Synthesis ◽  
Mercaptopropionic Acid ◽  
Antidiuretic Effect

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.

Synthesis of [1-β-mercaptopropionic acid, 8-D-arginine]vasopressin (DDAVP) in solid phase. Simple optimalization

1979 ◽  
Vol 44 (4) ◽  
pp. 1173-1178 ◽  
Author(s):  
Viktor Krchňák ◽  
Milan Zaoral
Keyword(s):  
Arginine Vasopressin ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Experimental Conditions ◽  
Phase Synthesis ◽  
Mercaptopropionic Acid ◽  
Better Than

A series of solid-phase syntheses of the protected precursor II of DDAVP was carried out. Experimental conditions were developed under which practically pure II can reproducibly be obtained in yields better than 60%. The protected precursors of DDAVP obtained by liquid- and solid-phase synthesis and DDAVP samples obtained from these precursors were undistinguishable by conventional analytical or pharmacological assays.

Sign in / Sign up

Export Citation Format

Share Document