ChemInform Abstract: AMINO ACIDS AND PEPTIDES PART 123, (4-LEUCINE, 8-D-ARGININE)- AND (1-BETA-MERCAPTOPROPIONIC ACID, 4-LEUCINE, 8-D-ARGININE)-VASOTOCIN, TWO VASOTOCIN ANALOGS WITH SPECIFIC ANTIDIURETIC EFFECT

1974 ◽  
Vol 5 (52) ◽  
pp. no-no
Author(s):  
M. ZAORAL ◽  
I. LAINE ◽  
F. BRTNIK
Keyword(s):  
Amino Acids ◽  
Arginine Vasotocin ◽  
Mercaptopropionic Acid ◽  
Antidiuretic Effect

[1-β-Mercaptopropionic acid, 8-norarginine]vasopressin and [1-β-mercaptopropionic acid, 8-D-norarginine]vasopressin. Two analogs with strong biological effects

1979 ◽  
Vol 44 (4) ◽  
pp. 1179-1186 ◽  
Author(s):  
Milan Zaoral ◽  
František Brtník ◽  
Martin Flegel ◽  
Tomislav Barth ◽  
Alena Machová
Keyword(s):  
Biological Effects ◽  
Disulfide Bridge ◽  
Protecting Groups ◽  
Pressor Effect ◽  
Amino Groups ◽  
Mercaptopropionic Acid ◽  
Antidiuretic Effect ◽  
Carbodiimide Method

[1-β-Mercaptopropionic acid, 8-norarginine]vasopressin (L8, D8; I, II) was prepared by condensation of β-benzylthiopropionyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteine with Nγ-benzyloxycarbonyl-α,γ-diaminobutyryl-glycine amide (L2, D2) by the azide or carbodiimide method, respectively, removal of the benzyloxycarbonyl residue, guanidination of γ-amino groups, removal of protecting groups, closing of the disulfide bridge, and electrophoretic purification. I has an almost 2 times higher antidiuretic effect than DDAVP and a 3 times higher pressor effect than AVP. II has 20-25% of the antidiuretic effect of DDAVP and 16 IU/mg of the pressor effect.

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.

Analysis of antidiuretic effect of arginine-vasotocin and its analogs in primates

2006 ◽  
Vol 142 (6) ◽  
pp. 714-716
Author(s):  
L. B. Buravkova ◽  
I. M. Larina ◽  
V. I. Korol’kov ◽  
I. V. Dobrokhotov ◽  
A. I. Grigor’ev
Keyword(s):  
Arginine Vasotocin ◽  
Antidiuretic Effect

[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.

[1-β-Mercaptopropionic acid, 8-α-amino-β-glycylaminopropionic acid]vasopressin. A vasopressin analog with an isopeptide structure in its molecule

1979 ◽  
Vol 44 (10) ◽  
pp. 3133-3136 ◽  
Author(s):  
Milan Zaoral ◽  
Viktor Krchňák ◽  
Jana Škopková ◽  
Alena Machová
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Mercaptopropionic Acid ◽  
Antidiuretic Effect

[1-β-Mercaptopropionic acid, 8-α-amino-β-glycylaminopropionic acid]vasopressin (II) was prepared by solid-phase peptide synthesis. II has an antidiuretic effect of considerable magnitude (435 I.U./mg) and specificity.

Sign in / Sign up

Export Citation Format

Share Document