Sulfur amino acids: from prebiotic chemistry to biology and vice versa

Synthesis ◽  
2021 ◽  
Author(s):  
Sparta Youssef-Saliba ◽  
Yannick Vallée
Keyword(s):  
Amino Acids ◽  
Essential Role ◽  
Prebiotic Chemistry ◽  
Prebiotic Synthesis ◽  
Sulfur Amino Acids ◽  
Methionine Residue ◽  
Catalytic Sites ◽  
Protein Amino Acids ◽  
Sulfur Containing

Two sulfur containing amino acids are included in the list of the 20 classical protein amino acids. A methionine residue is introduced at the start of the synthesis of all current proteins. Cysteine, thanks to its thiol function, plays an essential role in a very large number of catalytic sites. Here we present what is known about the prebiotic synthesis of these two amino acids and homocysteine, and we discuss their introduction into primitive peptides and more elaborate proteins.

scholarly journals Effects of Sulfur Amino Acids on Cardiodynamic Parameters of Isolated Rat Heart

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Nikola Sobot ◽  
Tanja Sobot ◽  
Katarina Radonjic ◽  
Tamara Nikolic Turnic ◽  
Anica Petkovic ◽  
...  
Keyword(s):  
Amino Acids ◽  
Cardiac Function ◽  
Molecular Mechanisms ◽  
Isolated Rat Heart ◽  
Oxidation States ◽  
Sulfur Amino Acids ◽  
Negative Effects ◽  
Sulphur Amino Acids ◽  
The Impact ◽  
Sulfur Containing

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.

Distribution and possible biosynthetic pathway of non-protein sulfur amino acids in legumes

2019 ◽  
Vol 70 (16) ◽  
pp. 4115-4121 ◽  
Author(s):  
Jaya Joshi ◽  
Elham Saboori-Robat ◽  
Mahmood Solouki ◽  
Motahhareh Mohsenpour ◽  
Frédéric Marsolais
Keyword(s):  
Amino Acids ◽  
Biosynthetic Pathway ◽  
Protein Quality ◽  
Protein Composition ◽  
Grain Legumes ◽  
Sulfur Amino Acids ◽  
Vigna Species ◽  
Protein Amino Acids ◽  
Two Phases

Abstract Some grain legumes store sulfur in the form of non-protein amino acids in seed. γ-Glutamyl-S-methylcysteine is found in Phaseolus and several Vigna species. γ-Glutamyl-S-ethenylcysteine, an antinutritional compound, is present in Vicia narbonensis. In P. vulgaris, free S-methylcysteine levels are higher at early stages of seed development followed by a decline. γ-Glutamyl-S-methylcysteine accumulates later, in two phases, with a lag during reserve accumulation. The concentration of total S-methylcysteine, quantified after acid hydrolysis, is positively regulated by sulfate nutrition. The levels of both γ-glutamyl-S-methylcysteine and γ-glutamyl-S-ethenylcysteine are modulated in response to changes in seed protein composition. A model is proposed whereby the majority of γ-glutamyl-S-methylcysteine in P. vulgaris is synthesized via the intermediate S-methylhomoglutathione. Knowledge of the biosynthesis of non-protein sulfur amino acids is required for metabolic engineering approaches, in conjunction with manipulation of the protein sink, to increase the concentration of nutritionally essential methionine and cysteine. This would improve protein quality of some important legume crops.

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
Keyword(s):  
Amino Acids ◽  
Glutamic Acid ◽  
Acid Anhydride ◽  
Sulfur Amino Acids ◽  
Protecting Group ◽  
One Pot ◽  
Derivatives Of ◽  
Sulfur Containing ◽  
Nutraceutical Properties ◽  
Flavor Enhancer

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.

scholarly journals Prebiotic Synthesis of Hydrophobic and Protein Amino Acids

1972 ◽  
Vol 69 (3) ◽  
pp. 765-768 ◽  
Author(s):  
D. Ring ◽  
Y. Wolman ◽  
N. Friedmann ◽  
S. L. Miller
Keyword(s):  
Amino Acids ◽  
Prebiotic Synthesis ◽  
Protein Amino Acids

scholarly journals Metabolism of Sulfur-containing Amino Acids by Pregnant Merino Ewes

1988 ◽  
Vol 41 (2) ◽  
pp. 247 ◽  
Author(s):  
AJ Williams ◽  
R Murison ◽  
J Padgett
Keyword(s):  
Amino Acids ◽  
Organic Sulfur ◽  
Sulfur Amino Acids ◽  
Sulfur Containing

The availability and utilization of cystine and methionine were measured in single-bearing Merino ewes on three occasions, approximately 90, 110 and 130 days after mating, and the effects on these traits of sulfur amino acids (SAA) infused into the abomasum were also measured. Two levels of SAA were infused containing 0�5 or 1�0 g day-i organic sulfur with DL-methionine contributing two-thirds and L-cystine onethird of the supplementary sulfur. The quantity of the diet offered was increased at each occasion so as to maintain maternal liveweight.

Adsorption of amino acids and nucleic acid bases onto minerals: a few suggestions for prebiotic chemistry experiments

2012 ◽  
Vol 11 (4) ◽  
pp. 229-234 ◽  
Author(s):  
Dimas A.M. Zaia
Keyword(s):  
Amino Acids ◽  
Nucleic Acid ◽  
Origin Of Life ◽  
Prebiotic Chemistry ◽  
Synthesis Methods ◽  
Nucleic Acid Bases ◽  
The Earth ◽  
Protein Amino Acids ◽  
The Origin Of Life ◽  
Living Organisms

AbstractAmino acids and nucleic acid bases are very important for the living organisms. Thus, their protection from decomposition, selection, pre-concentration and formation of biopolymers are important issues for understanding the origin of life on the Earth. Minerals could have played all of these roles. This paper discusses several aspects involving the adsorption of amino acids and nucleic acid bases onto minerals under conditions that could have been found on the prebiotic Earth; in particular, we recommend the use of minerals, amino acids, nucleic acid bases and seawater ions in prebiotic chemistry experiments. Several experiments involving amino acids, nucleic acid bases, minerals and seawater ions are also suggested, including: (a) using well-characterized minerals and the standardization of the mineral synthesis methods; (b) using primary chondrite minerals (olivine, pyroxene, etc.) and clays modified with metals (Cu, Fe, Ni, Mo, Zn, etc.); (c) determination of the possible products of decomposition due to interactions of amino acids and nucleic acid bases with minerals; (d) using minerals with more organophilic characteristics; (e) using seawaters with different concentrations of ions (i.e. Na+, Ca2+, Mg2+, SO42− and Cl−); (f) using non-protein amino acids (AIB, α-ABA, β-ABA, γ-ABA and β-Ala and g) using nucleic acid bases other than adenine, thymine, uracil and cytosine. These experiments could be useful to clarify the role played by minerals in the origin of life on the Earth.

scholarly journals Biosynthesis of food constituents: Amino acids: 4. Non-protein amino acids – a review

2011 ◽  
Vol 24 (No. 3) ◽  
pp. 93-109 ◽  
Author(s):  
J. Velíšek ◽  
R. Kubec ◽  
K. Cejpek
Keyword(s):  
Amino Acids ◽  
Review Article ◽  
Basic Amino Acids ◽  
Hydroxyamino Acids ◽  
Protein Amino Acids ◽  
Sulfur Containing

This review article gives a brief survey of the principal pathways that lead to the biosynthesis of the most important non-protein amino acids occurring in foods and feeds. These amino acids have been divided into the following groups: 3-amino acids and 4-amino acids, N-substituted amino acids, alicyclic amino acids, hydroxyamino acids, sulfur-containing amino acids, basic amino acids, and taurine.  

scholarly journals Prebiotic Synthesis of α-Amino Acids and Orotate from α-Ketoacids Potentiates Transition to Extant Metabolic Pathways

2021 ◽  
Author(s):  
Ramanarayanan Krishnamurthy ◽  
Sunil Pulletikurti ◽  
Mahipal Yadav ◽  
Greg Springsteen
Keyword(s):  
Amino Acids ◽  
Metabolic Pathways ◽  
Prebiotic Chemistry ◽  
Krebs Cycle ◽  
Prebiotic Synthesis ◽  
Biological Pathways ◽  
Subsequent Evolution ◽  
Simultaneous Formation ◽  
Strecker Reaction ◽  
Seamless Transition

Abstract The Strecker reaction of aldehydes is the preeminent pathway to explain the prebiotic origins of a-amino acids. However, biology employs transamination of a-ketoacids to give rise to amino acids which are then transformed to nucleobases, implying subsequent evolution of the biosynthetic pathways – abiotically or biotically. Herein, we show that a-ketoacids react with cyanide and ammonia sources to form the corresponding a-amino acids – via the Bucherer-Bergs pathway. An efficient prebiotic transformation of oxaloacetate to aspartate via N-carbamoyl aspartate enables the simultaneous formation of dihydroorotate, paralleling the biochemical synthesis of orotate as the precursor to pyrimidine nucleobases. Glyoxylate forms both glycine and orotate, and reacts with malonate and urea to form aspartate and dihydroorotate. These results, along with the previously demonstrated protometabolic analogs of the Krebs cycle suggest that there can be a natural emergence of congruent forerunners of biological pathways with the potential for seamless transition from prebiotic chemistry to modern metabolism.

Methionine-Specific Staining of Collagen

1982 ◽  
Vol 40 ◽  
pp. 294-295
Author(s):  
E.M. Kuhn ◽  
K.D. Marenus ◽  
M. Beer
Keyword(s):  
Amino Acids ◽  
Collagen Fibers ◽  
Type Iii Collagen ◽  
Type I ◽  
Electron Microscopic ◽  
Good Correspondence ◽  
Specific Staining ◽  
Type Iii ◽  
Different Types ◽  
Sulfur Containing

Fibers composed of different types of collagen cannot be differentiated by conventional electron microscopic stains. We are developing staining procedures aimed at identifying collagen fibers of different types.Pt(Gly-L-Met)Cl binds specifically to sulfur-containing amino acids. Different collagens have methionine (met) residues at somewhat different positions. A good correspondence has been reported between known met positions and Pt(GLM) bands in rat Type I SLS (collagen aggregates in which molecules lie adjacent to each other in exact register). We have confirmed this relationship in Type III collagen SLS (Fig. 1).

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