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.

[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.

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.

[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.

Solid Phase Synthesis of a Somatostatin Amide Analogue Using Acid Labile t-Bumeoc Protection and an Acid Labile Anchor Group

1992 ◽  
Vol 57 (8) ◽  
pp. 1707-1718
Author(s):  
Wolfgang Voelter ◽  
Gerhard Breipohl ◽  
Chryssa Tzougraki ◽  
Eveline Jungfleisch-Turgut
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Somatostatin Analogue ◽  
Phase Synthesis ◽  
Anchor Group ◽  
Amide Form ◽  
Polystyrene Resin ◽  
Acid Labile

The solid phase synthesis of an amidated somatostatin analogue based on the principle of differentiated acidolysis is described. The acid labile and smoothly cleavable t-Bumeoc moiety (1% TFA/DCM) is used for temporary Nα-protection of D- and L-amino acids and [4-[[[9H-fluoren-9-yl-methoxycarbonyl]amino](4-methoxyphenyl)methyl]-2-methylphenoxy]acetic acid, attached to an aminomethylated polystyrene resin is used as acid sensitive linker of the solid carrier which releases the peptide in its amide form by treatment with TFA. Its preparation is described in detail.

Sequentially Photocleavable Protecting Groups in Solid-Phase Synthesis

2003 ◽  
Vol 5 (8) ◽  
pp. 1179-1181 ◽  
Author(s):  
Martin Kessler ◽  
Ralf Glatthar ◽  
Bernd Giese ◽  
Christian G. Bochet
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Protecting Groups ◽  
Phase Synthesis

Festphasensynthese von Muramyldipeptiden an isomeren Trialkoxybenzylamin-Harzen / Solid Phase Synthesis of Muramyl Dipeptides on Isomeric Trialkoxybenzylamine Resins

1998 ◽  
Vol 53 (7) ◽  
pp. 753-764 ◽  
Author(s):  
Hans-Jürgen Kohlbaua ◽  
Jochen Tschakert ◽  
Raed A. Al-Qawasmeh ◽  
Tanveer Ahmad Nizamì ◽  
Abdul Malik ◽  
...  
Keyword(s):  
Amino Acids ◽  
Trifluoroacetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Subsequent Treatment ◽  
Phase Synthesis ◽  
Merrifield Resin

Abstract New isomeric trialkoxybenzylamine resins are developed coupling phthalimidomethyl-3,5-dimethoxyphenols to the Merrifield resin, followed by subsequent treatment with hydrazine. The generated benzylamine function allows DCC coupling w ith the carboxyl function of amino acids and peptides which are removed as amides after treatment with trifluoroacetic acid. These new trialkoxybenzylamine resins allow expeditious syntheses of peptide amides and glycopeptide amides as is demonstrated for muramyl peptides and analogues.

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