Mimicking bioactive peptides. [8-Nβ-Guanidoacetyl-α,β-diaminopropionic acid]vasopressin

1989 ◽  
Vol 54 (2) ◽  
pp. 533-535
Author(s):  
Milan Zaoral ◽  
Viktor Krchňák
Keyword(s):  
Title Compound ◽  
Bioactive Peptides ◽  
Solid Phase ◽  
Antidiuretic Activity ◽  
Pressor Activity ◽  
Diaminopropionic Acid

The title compound was prepared by solid phase methodology. It has 34.2 I.U./mg of pressor activity, 5.8 I.U./mg of uterotonic activity and by 3-4 orders of magnitude lower antidiuretic activity than DDAVP.

Vasopressin analogues modified in positions 2, 3 and 8. Synthesis and biological effects

1983 ◽  
Vol 48 (5) ◽  
pp. 1341-1351 ◽  
Author(s):  
Ivo Bláha ◽  
Danuta Konopinska ◽  
Milan Zaoral
Keyword(s):  
Amino Acid ◽  
Solid Phase ◽  
Biological Effects ◽  
Solution Synthesis ◽  
Antidiuretic Activity ◽  
Pressor Activity ◽  
Vasopressin Analogues

Four vasopressin analogues, modified in positions 2, 3 and 8 were prepared by solid phase as well as solution synthesis. Analogues, containing a D-amino acid in position 3, exhibit a low but markedly specific antidiuretic activity. Analogues with a D-substituent in position 2 show a more specific pressor activity.

scholarly journals (S)-2-[(4-Fluorophenyl)formamido]-3-phenylpropanoic acid

IUCrData ◽  
2020 ◽  
Vol 5 (7) ◽  
Author(s):  
Kathleen S. Lee ◽  
Luke Turner ◽  
Cynthia B. Powell ◽  
Eric W. Reinheimer
Keyword(s):  
Hydrogen Bonding ◽  
Title Compound ◽  
Phenyl Ring ◽  
Room Temperature ◽  
Solid Phase ◽  
Independent Molecule ◽  
Asymmetric Unit ◽  
Torsion Angles ◽  
Compound C ◽  
Independent Molecules

The title compound, C16H14FNO3, was synthesized via solid phase methods; it exhibits monoclinic (P21) symmetry at room temperature. The two independent molecules that comprise the asymmetric unit display distinct torsion angles of 173.2 (2) and 72.6 (2)° along the central sp 3 C—N bond. In the crystal, hydrogen bonding through N—H...O contacts couples the asymmetric unit molecules into pairs that align in layers extending parallel to (100) via additional O—H...O interactions. The phenyl ring of one independent molecule was found to be disordered over two sets of sites in a 0.55 (3):0.45 (3) ratio.

scholarly journals Synthesis and vibrational spectral (FT-IR, FT-Raman) studies, NLO properties & NBO analysis of (E)-N'(thiophen-2yl methylene)isonicotinohydrazide using quantum chemical method

2018 ◽  
Vol 6 (1) ◽  
pp. 53
Author(s):  
Nathiya A ◽  
Saleem H ◽  
Bharanidharan Bharani ◽  
Suresh M
Keyword(s):  
Molecular Orbital ◽  
Title Compound ◽  
Solid Phase ◽  
Nbo Analysis ◽  
Basis Set ◽  
Excitation Energies ◽  
Charge Delocalization ◽  
Nlo Properties ◽  
Ft Ir ◽  
Ft Raman

FT-IR (4000-400 cm-1) and FT-Raman (3500-50 cm-1) spectra of (E)-N'(thiophen-2yl methylene)isonicotinohydrazide (TMINH) molecule was recorded in solid phase. The optimized geometry was calculated by B3LYP method with 6-311++G(d,p) basis set. The harmonic vibrational frequencies, infrared (IR) intensities and Raman scattering activities of the title compound were performed at same level of theory. The complete vibrational assignments were performed on the basis of the Total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanical (SQM) method. The calculated first hyperpolarizability may be attractive for further studies on non-linear optical (NLO) properties of material. Stability of the molecule arising from hyperconjugative interaction and charge delocalization was analyzed using natural bond orbital (NBO) analysis. Highest occupied molecular orbital-Lowest unoccupied molecular orbital (HOMO-LUMO) energy gap explains the eventual charge transfer interactions taking place within the title molecule. A study on the electronic properties, such as excitation energies and wavelengths, were performed by time-dependent (TD-DFT) approach. Molecular electrostatic potential (MEP) provides the information on the electrophilic, nucleophilic and free radical prone reactive sites of the molecule. The thermodynamic properties such as heat capacity, entropy and enthalpy of the title compound were calculated at different temperatures in gas phase. 1H and 13C-NMR chemical shifts of the molecule were calculated using Gauge-independent atomic orbital (GIAO) method.To establish information about the interactions between human cytochrome protein and this novel compound theoretically, docking studies were carried out using Schrödinger software.

[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.

First aromatic electrophilic iodination reaction on the solid-phase: Iodination of bioactive peptides

1998 ◽  
Vol 39 (40) ◽  
pp. 7393-7396 ◽  
Author(s):  
Gemma Arsequell ◽  
Gemma Espuña ◽  
Gregorio Valencia ◽  
José Barluenga ◽  
Raquel Pérez Carlón ◽  
...  
Keyword(s):  
Bioactive Peptides ◽  
Solid Phase ◽  
Iodination Reaction

Detection and analysis of urinary peptides by on-line liquid chromatography and mass spectrometry: application to patients with renal Fanconi syndrome

2003 ◽  
Vol 104 (5) ◽  
pp. 483-490 ◽  
Author(s):  
Pedro R. CUTILLAS ◽  
Anthony G.W. NORDEN ◽  
Rainer CRAMER ◽  
Alma L. BURLINGAME ◽  
Robert J. UNWIN
Keyword(s):  
Mass Spectrometry ◽  
Liquid Chromatography ◽  
Bioactive Peptides ◽  
Solid Phase ◽  
Tubular Function ◽  
Renal Fanconi Syndrome ◽  
Dent’S Disease ◽  
Dent's Disease ◽  
On Line ◽  
Urinary Peptides

Urinary proteomics has become a topical and potentially valuable field of study in relation to normal and abnormal renal function. Filtered bioactive peptides present in high concentration in the nephron of patients with tubular proteinuria may have downstream effects on renal tubular function. In renal Fanconi syndromes, such as Dent's disease, peptides implicated in altered tubular function or injury have recently been measured in urine by immunochemical methods. However, the limited availability of antibodies means that only certain peptides can be detected in this way. We have used nanoflow liquid chromatography and tandem mass spectrometry (nanoLC-MS/MS) as a complementary technique to analyse urinary peptides. Urine was desalted by solid-phase extraction (SPE) and its peptides were then separated from neutral and acidic compounds by strong cation-exchange chromatography (SCX), which was also used to fractionate the peptide mixture. Fractions from the SCX step were separated further by reversed-phase LC and analysed on-line by MS/MS. Extraction by SPE showed a good recovery of small peptides. We detected over 100 molecular species in urine samples from three individuals with Dent's disease. In addition to plasma and known urinary proteins, we identified some novel proteins and potentially bioactive peptides in urine from these patients, which were not present in normal urine. These data show that nanoLC-MS/MS complements existing techniques for the identification of polypeptides in urine. This approach is a potentially powerful tool to discover new markers and/or causative factors in renal disease; in addition, its sensitivity may also make it applicable to the direct ultramicroanalysis of renal tubule fluid.

Antagonistic Analogs of Oxytocin with Substituted Phenylalanine or Tyrosine in Position 2

1994 ◽  
Vol 59 (6) ◽  
pp. 1430-1438 ◽  
Author(s):  
Rudolf Ježek ◽  
Miroslava Žertová ◽  
Jiřina Slaninová ◽  
Pavel Majer ◽  
Zdenko Procházka
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Phase Method ◽  
Inhibiting Activity ◽  
Structure Activity ◽  
Low Degree ◽  
Solid Phase Method ◽  
Pressor Activity ◽  
Agonistic Activity

Solid phase method on p-methylbenzhydrylamine resin was used for the synthesis of seven analogs of oxytocin with non-coded amino acids in position 2. [L-Phe(4-Me)2]oxytocin (I), [D-Phe(4-Me)2]oxytocin (II), [L-Phe(2-Me,4-Et)2]oxytocin (III), [D-Phe(2-Me,4-Et)2]oxytocin (IV), [D-Tyr(Me)2]oxytocin (V), [D-Tyr(Et)2]oxytocin (VI) and [L-Tyr(2-Me)2]oxytocin (VII) were synthesized. All analogs with D-stereoisomer of alkyl or alkoxy substituted phenylalanine possess uterus in vitro inhibiting activity. In the case of L-stereoisomers the structure activity relationship is more complicated. As far as the pressor activity is concerned, the analogs have either very low agonistic activity or low degree of antagonism.

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