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.

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.

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.

[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.

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.

Oxytocin analogues with non-coded amino acid residues in position 8: [8-Neopentylglycine]oxytocin and [8-cycloleucine]oxytocin

1987 ◽  
Vol 52 (9) ◽  
pp. 2317-2325 ◽  
Author(s):  
Jan Hlaváček ◽  
Jan Pospíšek ◽  
Jiřina Slaninová ◽  
Walter Y. Chan ◽  
Victor J. Hruby
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Other ◽  
Amino Acid Residues ◽  
Phase Synthesis ◽  
Other Hand ◽  
Fragment Condensation

[8-Neopentylglycine]oxytocin (II) and [8-cycloleucine]oxytocin (III) were prepared by a combination of solid-phase synthesis and fragment condensation. Both analogues exhibited decreased uterotonic potency in vitro, each being about 15-30% that of oxytocin. Analogue II also displayed similarly decreased uterotonic potency in vivo and galactogogic potency. On the other hand, analogue III exhibited almost the same potency as oxytocin in the uterotonic assay in vivo and in the galactogogic assay.

Solid Phase Synthesis of Novel Fullerene Nucleotides Conjugates

2011 ◽  
Vol 266 ◽  
pp. 200-203
Author(s):  
Jing Zhang ◽  
Ya Dong Zhang
Keyword(s):  
Aspartic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Properties ◽  
Azomethine Ylide ◽  
Hydroxyl Group ◽  
Spectrometric Analysis ◽  
Phase Synthesis ◽  
Chemical Structures ◽  
Controlled Pore Glass

N-substituted 3, 4-fullero pyrrolidine was synthesized according to 1, 3-dipolar cycloaddition of the azomethine ylide. Aspartic acid with protected α-amino and α-carboxyl groups was reacted with the activated hydroxyl group of N-substituted 3, 4-fullero pyrrolidine. The products were deprotected, affording the monofullerene aspartic acid (mFas). The conjugate FasT was synthesized by reaction of mFas containing protected amino group with the thymidylic acid derivatived controlled pore glass (CPG) using solid phase synthesis. All of the above fullerene derivatives were characterized by UV–vis, 1H NMR, IR and MS spectrometric analysis, giving the correct spectra with regard to their chemical structure. The chemical structures of fullerene nucleotides conjugate FasT is different from previous reports and may have novel biological properties. Moreover, they are more suitable for applications in biomedical research due to their solubilization in THF and DMSO. They have a potential to be used as monomer for the automatic synthesis. It allows further conjugation with specific biomolecules including amino acids, peptides, nucleotides and nucleic acids. A novel method has been developed to synthesize fullerene nucleotides conjugate. Their unique chemical structures make them very interesting for their potential use in medicine and biology.

[MeArg1, NLe10]-apelin-12: Optimization of solid-phase synthesis and evaluation of biological properties in vitro and in vivo

Peptides ◽  
2020 ◽  
Vol 129 ◽  
pp. 170320 ◽  
Author(s):  
Maria Sidorova ◽  
Irina Studneva ◽  
Valery Bushuev ◽  
Marina Pal’keeva ◽  
Alexander Molokoedov ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Properties ◽  
Phase Synthesis

scholarly journals Postsynthetic On-Column 2′ Functionalization of RNA by Convenient Versatile Method

2020 ◽  
Vol 21 (14) ◽  
pp. 5127
Author(s):  
Olga A. Krasheninina ◽  
Veniamin S. Fishman ◽  
Alexander A. Lomzov ◽  
Alexey V. Ustinov ◽  
Alya G. Venyaminova
Keyword(s):  
Chemical Synthesis ◽  
Physicochemical Properties ◽  
Functional Groups ◽  
Convenient Method ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Protecting Groups ◽  
Hydroxyl Group ◽  
Phase Synthesis ◽  
Wide Range

We report a universal straightforward strategy for the chemical synthesis of modified oligoribonucleotides containing functional groups of different structures at the 2′ position of ribose. The on-column synthetic concept is based on the incorporation of two types of commercial nucleotide phosphoramidites containing orthogonal 2′-O-protecting groups, namely 2′-O-thiomorpholine-carbothioate (TC, as “permanent”) and 2′-O-tert-butyl(dimethyl)silyl (tBDMS, as “temporary”), to RNA during solid-phase synthesis. Subsequently, the support-bound RNA undergoes selective deprotection and follows postsynthetic 2′ functionalization of the naked hydroxyl group. This convenient method to tailor RNA, utilizing the advantages of solid phase approaches, gives an opportunity to introduce site-specifically a wide range of linkers and functional groups. By this strategy, a series of RNAs containing diverse 2′ functionalities were synthesized and studied with respect to their physicochemical properties.

A convenient solid-phase synthesis methodology for preparing peptide-derived molecular imaging agents — Synthesis, characterization, and in vitro screening of Tc(I) – chemotactic peptide conjugates

2005 ◽  
Vol 83 (12) ◽  
pp. 2060-2066 ◽  
Author(s):  
Karin A Stephenson ◽  
Sangeeta Ray Banerjee ◽  
Nicole McFarlane ◽  
Douglas R Boreham ◽  
Kevin P Maresca ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Metal Chelate ◽  
Free Ligand ◽  
Peptide Sequence ◽  
In Vitro Screening ◽  
Chemotactic Peptide ◽  
Phase Synthesis ◽  
Synthesis Strategy

A versatile solid-phase synthesis strategy for preparing peptide–chelate conjugates was developed. The methodology was optimized using a series of ligands, designed to bind Tc(I)/Re(I), and a chemotactic peptide fMFL, which was exploited as a model targeting vector. The peptide derivatives were prepared in parallel using a conventional automated peptide synthesizer in multi-milligram quantities, which provided sufficient material to perform complete characterization, radiolabelling, and in vitro screening studies. Because of the robust nature of the metal–chelate complexes, the Re complex of a chelate–peptide conjugate was prepared on the resin using the same methodology employed to prepare the free ligand conjugates. As such, the reported methodology is amenable to the preparation of libraries of novel Tc radiopharmaceutical ligands and their corresponding Re reference standards in which several factors, including peptide sequence, site of derivatization, and both the type and length of the spacer, can be easily varied.Key words: radiopharmaceuticals, technetium, rhenium, peptides, solid-phase synthesis.

Solid-phase synthesis and in vitro biological activity of a Thr4→Ser4 analog of daptomycin

2015 ◽  
Vol 25 (23) ◽  
pp. 5490-5494 ◽  
Author(s):  
Chuda Raj Lohani ◽  
Robert Taylor ◽  
Michael Palmer ◽  
Scott D. Taylor
Keyword(s):  
Biological Activity ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis
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