Solid phase synthesis of [1-deamino,4-valine]-8-D-arginine-vasopressin (DVDAVP), a highly potent and specific antidiuretic agent possessing protracted effects

1973 ◽  
Vol 16 (9) ◽  
pp. 975-978 ◽  
Author(s):  
Maurice Manning ◽  
Lajos Balaspiri ◽  
Margot Acosta ◽  
Wilbur H. Sawyer
Keyword(s):  
Arginine Vasopressin ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

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.

A modified benzhydrylamine - A useful handle reagent for Fmoc based solid phase synthesis of peptide amides

1988 ◽  
Vol 53 (11) ◽  
pp. 2791-2800 ◽  
Author(s):  
Susumu Funakoshi ◽  
Eigoro Murayama ◽  
Lili Guo ◽  
Nobutaka Fujii ◽  
Haruaki Yajima
Keyword(s):  
Propionic Acid ◽  
Arginine Vasopressin ◽  
Trifluoroacetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biologically Active ◽  
Molar Ratio ◽  
Phase Synthesis ◽  
Active Peptide ◽  
Biologically Active Peptide

Usefulness of a dimethoxybenzhydrylamine derivative, 3-(3-(Fmoc-amino-4-methoxyphenylmethyl)-4-methoxyphenyl)propionic acid, for Fmoc-based solid phase synthesis of peptide amides was demonstrated by preparation of three biologically active peptide amides, i.e. tetragastrin, neuromedin B and [8-arginine]vasopressin. 1M trimethylsilyl bromide-thioanisole (molar ratio 1 : 1) in trifluoroacetic acid was recommended as a deprotecting reagent for releasing the peptide amides from the resin.

2-O-methyl and 2-O-ethyl-tyrosine derivatives of [8-arginine]vasopressin analogs: Highly specific antidiuretic agonists

1988 ◽  
Vol 53 (11) ◽  
pp. 2617-2626 ◽  
Author(s):  
Krzysztof Bankowski ◽  
Bernard Lammek ◽  
Marian Kruszynski ◽  
Maurice Manning ◽  
Janny Seto ◽  
...  
Keyword(s):  
Arginine Vasopressin ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Rat Uterus ◽  
Phase Synthesis ◽  
Neurohypophyseal Hormones ◽  
Tyrosine Derivatives ◽  
Activity Ratios ◽  
Treatment Of Diabetes ◽  
Derivatives Of

The solid phase synthesis of seven 2-O-methyl- and 2-O-ethyl-tyrosine substituted analogs of [8-arginine]vasopressin (AVP) with enhanced antidiuretic agonistic specificity is reported. These peptides are: [2-O-ethyltyrosine, 8-arginine]vasopressin (I), [2-O-methyltyrosine, 8-D-arginine]vasopressin (II), [2-O-ethyltyrosine, 8-D-arginine]vasopressin (III), [2-O-methyltyrosine, 4-valine, 8-arginine]vasopressin (IV), [2-O-ethyltyrosine, 4-valine, 8-arginine]vasopressin (V), [2-O-methyltyrosine, 4-valine, 8-D-arginine]vasopressin (VI), [2-O-ethyltyrosine, 4-valine, 8-D-arginine]vasopressin (VII). All analogs were tested for antidiuretic, antivasopressor and antioxytocic activities. Although all these new analogs are antidiuretic agonists they are antagonists of vasopressor responses to AVP, and of responses by the rat uterus to oxytocin. Thus, all seven new Tyr(Me) and Tyr(Et) containing analogs exhibit high antidiuretic specificity and have infinite antidiuretic/pressor (A/P) and antidiuretic/oxytocic (A/O) activity ratios. Some of these analogs e.g. Tyr(Me)DAVP, Tyr(Me)VAVP and Tyr(Me)VDAVP, which possess high antidiuretic activity with no pressor or oxytocic agonism, could be useful new pharmacological tools for characterizing receptors mediating specific responses to the neurohypophyseal hormones. They could also be potentially useful in the treatment of diabetes insipidus.

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.

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