scholarly journals Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure

Molbank ◽  
10.3390/m1147 ◽  
2020 ◽  
Vol 2020 (3) ◽  
pp. M1147
Author(s):  
Giovanna Speranza ◽  
Marco Rabuffetti ◽  
Nikolina Vidović ◽  
Carlo F. Morelli

γ-Glutamyl derivatives of sulfur amino acids have been prepared in multigram scale starting from readily available starting materials. The synthesis comprises two one-pot operations, both consisting of two reactions. In the first operation, N-phtaloyl-l-glutamic acid anhydride is obtained from l-glutamic acid and phtalic anhydride. In the second one, N-phtaloyl-l-glutamic acid anhydride is used to acylate amino acids and the N-phtaloyl protecting group is removed. The described approach offers a viable entry to γ-glutamyl derivatives of sulfur-containing amino acids with flavor-enhancer and nutraceutical properties.

2016 ◽  
Vol 14 (44) ◽  
pp. 10473-10480 ◽  
Author(s):  
Sylvain Daunay ◽  
Remi Lebel ◽  
Laurence Farescour ◽  
Jean-Claude Yadan ◽  
Irene Erdelmeier

Natural and novel sulfur-containing amino acids are preparedviaa new regioselective one-pot two-step procedure.


2021 ◽  
Vol 46 (4) ◽  
pp. 47-59
Author(s):  
Sof�a Rezende ◽  
Sabrina Banchero ◽  
Ignacio Migues ◽  
Mar�a Veronica Cesio ◽  
Carlos Fernando Rivas ◽  
...  

Nutraceutical properties of mandarins are of great interest to promote their consumption. The occurrence of free amino acids in foods is relevant to assess the nutritional value of it. To learn more about the amino acids� occurrence and variability between species, a targeted metabolomics study in �Ellendale�, �Willowleaf� and �Page� varieties was performed through ion exchange liquid chromatography coupled to tandem mass spectrometry. The studied amino acids were asparagine, glutamic acid, glutamine, histidine, methionine, phenylalanine, proline, threonine and tyrosine. The difference between two consecutive seasons was evaluated, as well as the influence of fruit maturity of �Page� collected in two periods of 2015. The analytical methodology was validated. The concentration of the compounds through principal component analysis, separated well apart the three cultivars in both harvests, showing a particular profile for each of them. When comparing mature and immature cultivar �Page�, the amino acids with higher levels in mature samples were histidine, asparagine, glutamine and glutamic acid. The profiles were different due to genetic diversity, and the climatic conditions. These results add value to citric production.


1941 ◽  
Vol 14 (2) ◽  
pp. 300-307 ◽  
Author(s):  
R. F. A. Altman

Abstract In a previous paper the separation and analysis of proteins remaining in rubber serum, after coagulating the rubber with formic acid, were described. The present paper is concerned with the properties and identification of the products thus isolated. As for nonamino acids, it may be recalled that these are composed mainly of the unsaponifiable thick brownish red oil A4. Of the other byproducts remaining to be identified, which were designated as BII, BIII, BV and BVI, only small amounts were obtained. Of the amino acids, alanine, arginine, asparagic acid, glutamic acid, histidine, leucine, ornithine, hydroxyproline, proline, tyrosine and valine were isolated in weighable amounts. In addition to these, it was possible to identify dihydroxyphenylalanine. In this connection the results obtained by Midgley, Henne and Renoll are of interest. These investigators found, as the principal components of proteins occurring in crepe rubber, the following amino acids: arginine, asparagic acid, glycine, histidine, leucine, lysine and proline. They considered it highly probable that alanine, phenylalanine, hydroxyproline and serine were also present in these proteins. On the other hand, it was definitely established that cystine, glutamic acid and tyrosine were not present. Table I summarizes the results of Midgley and his coworkers in comparison with ours. From this table it is evident that certain proteins, viz., those containing, among other compounds, tyrosine, glutamic acid and valine, do not coagulate with the rubber, but remain in the serum. The absence of sulfur-containing amino acids can probably be attributed to certain shortcomings in the analytical method. At any rate, the presence of sulfur in proteins precipitated from latex was established when the test was repeated.


1993 ◽  
Vol 71 (9) ◽  
pp. 1401-1406 ◽  
Author(s):  
Stephen Hanessian ◽  
Benoit Vanasse

Derivatives of L-aspartic and L-glutamic acids can be converted into α-hydroxy acids via oxygenation of the corresponding enolates.


1953 ◽  
Vol 51 (1) ◽  
pp. 140-144 ◽  
Author(s):  
J. Gordon

1. Glycine, alanine, and several isomers of alanine, DL-glutamic acid and DL-aspartic acid, when added to fresh guinea-pig serum and allowed to stand on the bench for half an hour, will protect the complement of this serum from destruction by heating at 55 and 56° C. for half an hour, but most of the complement activity is destroyed by heating at 57° C. and it is completely destroyed at 58° C. after half an hour.2. Derivatives of glycine do not have any protective effect.3. Various substances of high molecular weight, that might be described as ‘protective colloids’ do not have any protective effect.4. How these amino-acids when added to serum alter the heat-lability of the complement is not understood.


Author(s):  
Nikola Sobot ◽  
Tanja Sobot ◽  
Katarina Radonjic ◽  
Tamara Nikolic Turnic ◽  
Anica Petkovic ◽  
...  

AbstractSulfur-containing amino acids are integral part of molecular mechanisms which underlie many aspects of cellular function and homeostasis, facilitated by reversible changes in oxidation states of sulfur atoms. Dysregulation of these pathways is associated with diverse pathologies, notably of the cardiovascular system, which are typically characterized by inappropriate plasma levels of sulfur-containing amino acids. The aim of this study was to assess the acute, direct effects of sulfur-containing amino acids and inorganic NaHS, as H2S donor, on cardiodynamic parameters in homocysteine treated rats. Moderate hyperhomocysteinemia did not cause significant decrease in myocardial contractility, but our findings suggest that NaHS and L-methionine cause negative effects on cardiac function in hearts of the rats treated with homo-cysteine, even in a single administration. Further investigations need to be carried out with purpose of better understanding and highlightening the impact of Hcy and sulphur amino acids on cardiac function.


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