Preparation, spectral and physicochemical characteristics of methylamide Nα-phenylthiocarbamoyl derivatives of naturally occurring amino acids

1989 ◽  
Vol 54 (7) ◽  
pp. 1940-1954 ◽  
Author(s):  
Manfred Pavlík ◽  
Ivan Kluh ◽  
Františka Pavlíková ◽  
Soňa Vašíčková ◽  
Vladimír Kostka
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Infrared Spectra ◽  
Physicochemical Characteristics ◽  
Melting Points ◽  
H Nmr ◽  
Naturally Occurring ◽  
Derivatives Of ◽  
C Nmr

The methylamide Nα-phenylthiocarbamoyl derivatives of encoded amino acids II were prepared either by the addition of phenylisothiocyanate to amino acid methylamides or by the treatment of amino acid phenylthiohydantoins (5-alkyl-3-phenyl-2-thioxo-4-imidazolinones) I with methylamine. The derivatives were prepared of 19 amino acids and their melting points, 1H NMR, 13C NMR, mass, ultraviolet and infrared spectra were measured.

Preparation of Ureidonucleosides of the Threonine Isomers

1994 ◽  
Vol 49 (11-12) ◽  
pp. 834-842 ◽  
Author(s):  
Dierk Martin ◽  
Eckhard Schlimme
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Intermediate Compound ◽  
Side Chain ◽  
Biological Matrices ◽  
Preparative Scale ◽  
H Nmr ◽  
Amino Acid Side Chains ◽  
Nmr Signals ◽  
C Nmr

The hypermodified ureidonucleoside N6[((9-β-ᴅ-ribofuranosyl-9H-purine-6-yl)amino)carbonyl]- ʟ-threonine (5) is a constituent of transfer ribonucleic acid (tRNA) and is secreted as a tRNA catabolite in body fluids such as blood, milk and urine. Compound 5 and the isomeric ureidonucleosides bearing ᴅ-threonine (9), ʟ-allo- (7) and ᴅ-allo-threonine (11) as side chain moieties were synthesized on a preparative scale. The amido protons of 5 and 9 cause two separate 1H NMR signals whereas 7 and 11 cause multiplets. The 13C NMR signals of all carbon atoms of the allo-amino acid side chains (7, 11) are shifted downfield of the corresponding signals in compounds 5 and 9. The chemically protected intermediate compound adenosine urethane (3) is potentially of interest in the analysis of amino acids because it may be converted to nucleosides of the ureido type by reaction with amino acids in biological matrices.

scholarly journals Putative imbalanced amino acid metabolism in rainbow trout long term fed a plant-based diet as revealed by 1H-NMR metabolomics

2021 ◽  
Vol 10 ◽  
Author(s):  
Catherine Deborde ◽  
Blandine Madji Hounoum ◽  
Annick Moing ◽  
Mickaël Maucourt ◽  
Daniel Jacob ◽  
...  
Keyword(s):  
Amino Acids ◽  
Rainbow Trout ◽  
Amino Acid ◽  
Amino Acid Content ◽  
Proton Nuclear Magnetic Resonance ◽  
Free Form ◽  
Metabolomic Analysis ◽  
Nmr Metabolomics ◽  
H Nmr

Abstract The long-term effect of a plant (P)-based diet was assessed by proton nuclear magnetic resonance (1H-NMR) metabolomics in rainbow trout fed a marine fish meal (FM)–fish oil (FO) diet (M), a P-based diet and a control commercial-like diet (C) starting with the first feeding. Growth performances were not heavily altered by long-term feeding on the P-based diet. An 1H-NMR metabolomic analysis of the feed revealed significantly different soluble chemical compound profiles between the diets. A set of soluble chemical compounds was found to be specific either to the P-based diet or to the M diet. Pterin, a biomarker of plant feedstuffs, was identified both in the P-based diet and in the plasma of fish fed the P-based diet. 1H-NMR metabolomic analysis on fish plasma and liver and muscle tissues at 6 and 48 h post feeding revealed significantly different profiles between the P-based diet and the M diet, while the C diet showed intermediate results. A higher amino acid content was found in the plasma of fish fed the P-based diet compared with the M diet after 48 h, suggesting either a delayed delivery of the amino acids or a lower amino acid utilisation in the P-based diet. This was associated with an accumulation of essential amino acids and the depletion of glutamine in the muscle, together with an accumulation of choline in the liver. Combined with an anticipated absorption of methionine and lysine supplemented in free form, the present results suggest an imbalanced essential amino acid supply for protein metabolism in the muscle and for specific functions of the liver.

Synthesis of amino acid derivatives of indole-3-acetic acid

2005 ◽  
Vol 2005 (10) ◽  
pp. 640-642 ◽  
Author(s):  
Ying Liu ◽  
Liang Zhao ◽  
Liang Liu ◽  
Lin-Yi Wei ◽  
Lu-Hua Lai
Keyword(s):  
Acetic Acid ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
H Nmr ◽  
Derivatives Of ◽  
Indole 3 Acetic Acid

Amino acid derivatives of a modified indole-3-acetic acid have been synthesised. Fourteen new dipeptide-like compounds 3–4 were obtained and their structures were elucidated based on the IR, 1H NMR, MS spectra.

scholarly journals Regulation of rat magnocellular neurosecretory system by D-aspartate: evidence for biological role(s) of a naturally occurring free D-amino acid in mammals

2000 ◽  
Vol 167 (2) ◽  
pp. 247-252 ◽  
Author(s):  
H Wang ◽  
H Wolosker ◽  
J Pevsner ◽  
SH Snyder ◽  
DJ Selkoe
Keyword(s):  
Gene Expression ◽  
Amino Acids ◽  
Amino Acid ◽  
Physiological Function ◽  
Neurosecretory System ◽  
Milk Ejection ◽  
Magnocellular Neurons ◽  
Rat Hypothalamus ◽  
Naturally Occurring

Little evidence is available for the physiological function of D-amino acids in species other than bacteria. Here we demonstrate that naturally occurring freed -aspartate (D-Asp) is present in all magnocellular neurons of rat hypothalamus. The levels of this naturally occurring D-amino acid were elevated during lactation and returned to normal thereafter in the magnocellular neurosecretory system, which produces oxytocin, a hormone responsible for milk ejection during lactation. Intraperitoneal injections of D-Asp reproducibly increased oxytocin gene expression and decreased the concentration of circulating oxytocin in vivo. Similar changes were observed in the vasopressin system. These results provide evidence for the role(s) of naturally occurring free D-Asp in mammalian physiology. The findings argue against the conventional concept that only L-stereoisomers of amino acids are functional in higher species.

Chiral sensors for determining the absolute configurations of α-amino acid derivatives

2018 ◽  
Vol 16 (37) ◽  
pp. 8311-8317 ◽  
Author(s):  
Zhongxiang Chen ◽  
Hongjun Fan ◽  
Shiwei Yang ◽  
Guangling Bian ◽  
Ling Song
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
H Nmr ◽  
The Absolute

Two simple 1H NMR tests give the absolute configurations of α-amino acids.

Effects of some Amino-acid and Purine Antagonists on Chick Embryos

Development ◽  
1958 ◽  
Vol 6 (2) ◽  
pp. 365-372
Author(s):  
C. H. Waddington ◽  
Margaret Perry
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Effective Concentration ◽  
Metabolic Inhibitors ◽  
Chick Embryos ◽  
Purine Analogue ◽  
Know How ◽  
Naturally Occurring ◽  
Different Types ◽  
Strong Action

Several authors have studied the effects on developing embryos of substances which are analogues of naturally occurring amino-acids and purines, and known to act, in other systems, as metabolic inhibitors. It was emphasized by Waddington, Feldman, & Perry (1955) that any particular substance may exhibit very different effects in embryos of different types. They found, for instance, that the purine analogue 8-azaguanine has a very strong action in the chick and a much lesser one in the newt embryo. It is therefore necessary to consider the various classes of embryos separately. In this communication we shall be concerned only with chick embryos. Substances under test can be administered to such embryos by injection through the shell, as was done in the paper cited above With this technique it is impossible to know how much diffusion takes place of the substance injected, and one cannot therefore be certain of the effective concentration which actually reaches the embryo.

Chromopeptides from Phytochrome and Phycocyanin. NM R Studies o f the Pfr and Pr Chromophore of Phytochrome and E,Z Isomeric Chromophores of Phycocyanin

1983 ◽  
Vol 38 (5-6) ◽  
pp. 359-368 ◽  
Author(s):  
Fritz Thümmler ◽  
Wolfhart Rüdiger ◽  
Edmund Cmiel ◽  
Siegfried Schneider
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Avena Sativa ◽  
Maximum Amount ◽  
Acid Interaction ◽  
Spirulina Maxima ◽  
Nmr Spectrum ◽  
Pepsin Digestion ◽  
H Nmr ◽  
Amino Acid Interaction

Chromopeptides were prepared by pepsin digestion of C-phycocyanin isolated from the cyano­bacterium Spirulina maxima and of phytochrome isolated from seedlings of Avena sativa L. The chromopeptides were characterized by amino acid analysis. The ZZZ configurated chromophore of the phycocyanin peptide was transformed into its ZZE configurated isomer by the method of Falk et al. (Mh. Chemie 111, 159- 175, 1980) which had previously been applied to biliverdins. The 500 MHz 1HNMR spectrum of the ZZE configurated chromopeptides confirmed that its chromophore has the 15 E configuration. Irradiation yielded the ZZZ configurated isomer for which the 1H NMR spectrum was also recorded. Native phytochrome was irradiated at 660 nm to yield the maximum amount of the Pfr from (about 75% of total phytochrome). By digestion in the dark the previously described Pfr chromopeptide was obtained. The 500 MHz 1H NMR spectrum was compared with that of the ZZE phycocyanin peptide. It confirmed the 15 E con­figuration of the Pfr chromopeptide. Irradiation yielded the 15 Z configurated Pr chromopeptide. Comparison of the high resolution 1HNMR spectra of Pfr and Pr chromopeptides revealed that not only the chromophore resonances but also those of some amino acids are changed by the Pfr → Pr chromopeptide phototransformation. The results are discussed in terms of chromophore amino acid interaction.

β-Hydroxydithiozimtsäurederivate als Liganden. Synthese und Charakterisierung neuartiger 1,1-Ethendithiolato- und O,S-Chelatkomplexe / Derivatives of β -Hydroxydithiocinnamic Acids as Ligands. Syntheses and Characterisation of Novel 1,1-Ethenedithiolato and O,S-Chelate Complexes

2007 ◽  
Vol 62 (3) ◽  
pp. 475-482 ◽  
Author(s):  
Karsten Schubert ◽  
Helmar Görls ◽  
Wolfgang Weigand
Keyword(s):  
Bidentate Ligand ◽  
Molecular Structures ◽  
X Ray Diffraction ◽  
Chelate Complexes ◽  
X Ray ◽  
H Nmr ◽  
Hexyl Ester ◽  
Elemental Analyses ◽  
Derivatives Of ◽  
C Nmr

Starting from 4-bromoacetophenone 1, the 4-bromo-β -hydroxydithiocinnamic acid 2 and the 4-bromo-β -hydroxydithiocinnamic acid hexyl ester 3 were prepared using carbon disulfide and potassium-tert-butylate as a base. Acting as a ligand, the acid gives 1,1-ethenedithiolato complexes with (Ph3P)2Pt(II) (4a), (Et3P)2Pt(II) (4b), dppePt(II) (4c), (Ph3P)2Pd(II) (4d), dppePd(II) (4e), and dppeNi(II) (4f). In contrast to the acid, the deprotonated ester 3 forms a monoanionic bidentate ligand. [O,S] Complexes of Pt(II) (5a), Pd(II) (5b) and Ni(II) (5c) were obtained. All complexes have been fully characterised using 1H NMR, 13C NMR and 31P NMR spectroscopy, mass spectrometry, infrared spectroscopy and elemental analyses. The molecular structures of the complexes 4b and 5a - 5c were determined by X-ray diffraction analyses.

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