Synthesis and some pharmacological properties of [7-glycine, 8-ornithine]vasopressin and two of its analogues

1980 ◽  
Vol 45 (10) ◽  
pp. 2865-2871 ◽  
Author(s):  
Michal Lebl ◽  
Tomislav Barth ◽  
Jana Škopková ◽  
Karel Jošt
Keyword(s):  
Liquid Ammonia ◽  
Oxidative Cyclization ◽  
Protecting Groups ◽  
Pharmacological Properties ◽  
Lysine Vasopressin ◽  
Fragment Condensation ◽  
Depressor Effect ◽  
Protected Peptides

Protected peptides were prepared by fragment condensation according to the scheme 6 + 3 or 9 + 3, which, after the removal of the protecting groups by sodium in liquid ammonia and oxidative cyclization, afforded [7-glycine,8-ornithine]vasopressin, [7-glycine,8-ornithine]deaminovasopressin, and Nα-glycyl-glycyl-glycyl[7-glycine,8-ornithine]vasopressin. All the analogues had very low intrinsic vasopressin-like activities; the analogue with hormonogen nature had a depressor effect and inhibited the pressor action of lysine-vasopressin.

The synthesis and some pharmacological properties of [2-L-DOPA]-oxytocin

1976 ◽  
Vol 54 (5) ◽  
pp. 507-511 ◽  
Author(s):  
B. M. Ferrier ◽  
L. A. Branda
Keyword(s):  
Liquid Ammonia ◽  
Protecting Groups ◽  
Synthetic Analogue ◽  
Pharmacological Properties ◽  
Partition Chromatography ◽  
Alkaline Ph ◽  
Milk Ejection ◽  
Short Term ◽  
Naturally Occurring ◽  
Exclusion Chromatography

The first reported synthetic analogue of a naturally occurring peptide with a residue of L-3,4-dihydroxyphenylalanine (L-DOPA) was prepared by coupling N-carbobenzoxy-S-benzylcysteinyl-L-DOPA azide with isoleucylglutaminylasparaginyl-S-benzylcysteinylprolylleu-cylglycinamide. The protecting groups were removed from the resultant nonapeptide derivative by sodium in liquid ammonia and the peptide analogue was formed by short term oxidation of the dithiol-containing compound. It was isolated by sequential partition chromatography and exclusion chromatography on Sephadex G-25. It was unstable at neutral or alkaline pH. [2-L-DOPA]-oxytocin was found to possess a minimum milk-ejection-like activity of 54 ± 9 U/mg and uterotonic activity of 26 ± 4 U/mg. These potencies are approximately 12% and 5% of the corresponding potencies of oxytocin.

4-Phenylalanine analogues of vasopressin: Synthesis, pharmacological and chiroptical properties

1986 ◽  
Vol 51 (7) ◽  
pp. 1532-1541 ◽  
Author(s):  
František Brtník ◽  
Tomislav Barth ◽  
Petr Maloň ◽  
Ivo Frič ◽  
Vija E. Kluša ◽  
...  
Keyword(s):  
Arginine Vasopressin ◽  
Pharmacological Properties ◽  
Cd Spectra ◽  
Chiroptical Properties ◽  
Lysine Vasopressin ◽  
Vasopressin Synthesis

Synthesis, some pharmacological properties and CD spectra of [4-phenylalanine, 8-arginine]vasopressin and [4-phenylalanine, 8-lysine]vasopressin are described.

[3-(1,4-Cyclohexadienyl)-L-alanine,8-lysine]vasopressin synthesis and some pharmacological properties

1979 ◽  
Vol 22 (12) ◽  
pp. 1487-1492 ◽  
Author(s):  
Some Nath Banerjee ◽  
Lillian Diamond ◽  
Charlotte Ressler ◽  
Wilbur H. Sawyer
Keyword(s):  
Pharmacological Properties ◽  
Lysine Vasopressin ◽  
Vasopressin Synthesis

Synthesis of a polyphosphorylated GPI-anchor core structure

2002 ◽  
Vol 80 (8) ◽  
pp. 1105-1111 ◽  
Author(s):  
Martina Lahmann ◽  
Per J Garegg ◽  
Peter Konradsson ◽  
Stefan Oscarson
Keyword(s):  
Liquid Ammonia ◽  
Core Structure ◽  
Protecting Groups ◽  
Gpi Anchor ◽  
Linear Assembly ◽  
One Step ◽  
Cyclic Phosphate ◽  
The Common

Using a linear assembly approach a highly differentially protected derivative of the common GPI-anchor core structure (α-D-Man-(1[Formula: see text]6)-α-D-Man-(1[Formula: see text]2)-α-D-Man-(1[Formula: see text]4)-α-D-GlcNH2-(1[Formula: see text]6)-D-myo-inositol) has been synthesized. All mannose donors were prepared from a common thioglycoside precursor (1), and coupled to GlcN3-myo-inositol acceptor 5 in a linear five-step glycosylation–deprotection sequence in 49% overall yield, to give the key intermediate 10, with orthogonal temporary protecting groups at the 6'', 2'', 6', and 2 positions of the trimannoside motif and at the 1 and 2 positions of the inositol part. Consecutive removal of the temporary protecting groups in the trimannoside moiety followed by phosphorylation, gave a tetraphosphosphate derivative in 60% overall yield. Removal of a camphor acetal afforded a 1,2-inositol diol, which was converted to a 1,2-cyclic phosphate using commercial methyl dichlorophosphate ([Formula: see text]17, 95%). One-step deprotection using sodium in liquid ammonia afforded the target polyphosphorylated core structure 18 (60%), which will be tested for metabolic insulin action.Key words: glycophosphatidylinositols, linear synthesis, glycosylations, inositolphosphoglycans, IPG.

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