Identification and quantitation of the impurities in sodium pyruvate

Margolis, Sam A.; Coxon, Bruce

doi:10.1021/ac00125a033

Cited by 51 publications

(72 citation statements)

References 22 publications

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“…In contrast to many other organic acids, it has been shown that even at −20°C the sodium salt of pyruvic acid is reactive with formation of the dimer (11) (Fig. 1) and other compounds, probably oligomers (11,12). At 22°C dimer and oligomer formation can be seen in several minutes (12).…”

Section: The Formation Of Prebiotic Compounds By Pyruvate Chemistrymentioning

confidence: 97%

“…1) and other compounds, probably oligomers (11,12). At 22°C dimer and oligomer formation can be seen in several minutes (12).…”

Section: The Formation Of Prebiotic Compounds By Pyruvate Chemistrymentioning

confidence: 99%

“…A keto dicarboxylic acid (and dimer of pyruvic acid), 4-hydroxy-4-methyl-2-ketoglutaric acid (parapyruvic acid), is identified based on GC-MS interpretation of pyruvate reaction products (see below). This compound forms readily and is abundant in pyruvate solutions: it is a long known pyruvate condensation product (9)(10)(11)(12). To date, the most notable report of possible self-condensation products of organic compounds in meteorites involves the glycine peptide glycyl-glycine and its cyclic form, diketopiperazine.…”

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confidence: 99%

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Detection and formation scenario of citric acid, pyruvic acid, and other possible metabolism precursors in carbonaceous meteorites

Cooper

Reed

Nguyen

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

114

101

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Carbonaceous meteorites deliver a variety of organic compounds to Earth that may have played a role in the origin and/or evolution of biochemical pathways. Some apparently ancient and critical metabolic processes require several compounds, some of which are relatively labile such as keto acids. Therefore, a prebiotic setting for any such individual process would have required either a continuous distant source for the entire suite of intact precursor molecules and/or an energetic and compact local synthesis, particularly of the more fragile members. To date, compounds such as pyruvic acid, oxaloacetic acid, citric acid, isocitric acid, and α-ketoglutaric acid (all members of the citric acid cycle) have not been identified in extraterrestrial sources or, as a group, as part of a "one pot" suite of compounds synthesized under plausibly prebiotic conditions. We have identified these compounds and others in carbonaceous meteorites and/or as low temperature (laboratory) reaction products of pyruvic acid. In meteorites, we observe many as part of three newly reported classes of compounds: keto acids (pyruvic acid and homologs), hydroxy tricarboxylic acids (citric acid and homologs), and tricarboxylic acids. Laboratory syntheses using 13 C-labeled reactants demonstrate that one compound alone, pyruvic acid, can produce several (nonenzymatic) members of the citric acid cycle including oxaloacetic acid. The isotopic composition of some of the meteoritic keto acids points to interstellar or presolar origins, indicating that such compounds might also exist in other planetary systems.pyruvate | citrate | Murchison meteorite | Alan Hills | interstellar nitriles

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Section: The Formation Of Prebiotic Compounds By Pyruvate Chemistrymentioning

confidence: 97%

“…1) and other compounds, probably oligomers (11,12). At 22°C dimer and oligomer formation can be seen in several minutes (12).…”

Section: The Formation Of Prebiotic Compounds By Pyruvate Chemistrymentioning

confidence: 99%

mentioning

confidence: 99%

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Detection and formation scenario of citric acid, pyruvic acid, and other possible metabolism precursors in carbonaceous meteorites

Cooper

Reed

Nguyen

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

114

101

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“…Reaction mixtures contained Tris-HCl buffer (50 mM, pH 7.5, at 37°C), NH 4 Cl or KCl, Pta protein, and one substrate (plus allosteric effector, if added). In experiments that involved allosteric effectors, we used HEPES buffer (50 mM, pH 7.5) containing 100 mM KCl to prevent destruction of pyruvate by Tris buffer (54). Preincubation times were 1 min for the forward reaction and 2 min for the back reaction.…”

Section: In Vitro Activity Assays Phosphotransacetylase Activity Assaysmentioning

confidence: 99%

In Vivo and in Vitro Analyses of Single-amino Acid Variants of the Salmonella enterica Phosphotransacetylase Enzyme Provide Insights into the Function of Its N-terminal Domain

Brinsmade¹,

Escalante‐Semerena

2007

Journal of Biological Chemistry

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The function of the N-terminal domain (ϳ350 residues) of the Pta (phosphotransacetylase) enzyme of Salmonella enterica is unclear. Results from in vivo genetic and in vitro studies suggest that the N-terminal domain of Pta is a sensor for NADH and pyruvate. We isolated 10 single-amino acid variants of Pta that, unlike the wild-type protein, supported growth of a strain of S. enterica devoid of Acs (acetyl-CoA synthetase; AMP-forming) activity on 10 mM acetate. All mutations were mapped within the N-terminal domain of the protein.

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“…20,21) The decarboxylative selfcondensation of oxaloacetic acid and self-aldol condensation reaction of pyruvic acid in aqueous solution have also been reported. [22][23][24] However, to the best of our knowledge, the only example of a cross-aldol reaction of α-keto acids in an aqueous solution is the reaction of glyoxylic acid and oxaloacetic acid. 25,26) In this reaction, glyoxylic acid never underwent self-condensation, allowing for relatively easy production of a single condensed product.…”

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confidence: 99%

Preparation and Characterization of Four Stereoisomers of Monatin

et al. 2016

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Monatin is a naturally occurring, sweet amino acid comprising four stereoisomers due to its two asymmetric centers at C2 and C4. However, the characteristics of each stereoisomer have not yet been fully investigated. To obtain a sufficient amount of racemic monatin for optical resolution, a synthetic method was developed by modifying a possible biosynthetic pathway, i.e., a cross-aldol reaction and subsequent transamination. The key intermediate, 4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid, was obtained via the crossaldol reaction of pyruvic acid and indole-3-pyruvic acid. Subsequently, the carbonyl group was converted to a hydroxyimino group through reaction with hydroxylamine and then to an amino group via hydrogenation to produce monatin. Next, the racemic monatin was divided into mixtures of two pairs of enantiomers through recrystallization. Finally, both enantiomers of the N-carbobenzoxy-γ-lactone derivatives of monatin were separated by preparative HPLC and deprotected. It was found that all optically pure stereoisomers exhibited a sweet taste. The isomer that displayed the most intense sweetness was the (2R,4R)-isomer, as determined by single crystal X-ray structure analysis of the monatin potassium salt, whereas the least sweet isomer was the (2S,4S)-isomer, which demonstrated a far lower sweetness than was previously reported.

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Identification and quantitation of the impurities in sodium pyruvate

Cited by 51 publications

References 22 publications

Detection and formation scenario of citric acid, pyruvic acid, and other possible metabolism precursors in carbonaceous meteorites

Detection and formation scenario of citric acid, pyruvic acid, and other possible metabolism precursors in carbonaceous meteorites

In Vivo and in Vitro Analyses of Single-amino Acid Variants of the Salmonella enterica Phosphotransacetylase Enzyme Provide Insights into the Function of Its N-terminal Domain

Preparation and Characterization of Four Stereoisomers of Monatin

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