Keto-glutaric acid

Benzyl Methyl Ketone Beta Keto Glutaric Acid mono-Bromobenzene Butacaine... 

Cyclocondensation of 3-amino-2-methylaminopyridine 647 or 2-amino-3-methylaminopyridine 651 with 2-keto-glutaric acid gave 2-carboxyethyi-4-methylpyrido[2,3-i)]pyrazin-3(4/7)-one 652 and its 3-carboxyethyl-2(l/7)-one isomer 653, respectively (Equation 54) <1994FA259>. 

Amino acids get used up (making proteins, for example) so, to keep life going, ammonia must be brought in from somewhere. The key amino acid in this link is glutamic acid. A true reductive animation using NADPH and ammonia builds glutamic acid from a-keto-glutaric acid. 

Phenylketonuria (PKU) is an inborn error of metabolism by which the body is unable to convert surplus phenylalanine (PA) to tyrosine for use in the biosynthesis of, for example, thyroxine, adrenaline and noradrenaline. This results from a deficiency in the liver enzyme phenylalanine 4-mono-oxygenase (phenylalanine hydroxylase). A secondary metabolic pathway comes into play in which there is a transamination reaction between PA and a-keto-glutaric acid to produce phenylpyruvic acid (PPVA), a ketone and glutamic acid. Overall, PKU may be defined as a genetic defect in PA metabolism such that there are elevated levels of both PA and PPVA in blood and excessive excretion of PPVA (Fig. 25.7). 

B5. Banerjee, S., and Biswas, D. K., Urinary excretion of pyruvic acid, a-keto-glutaric acid, and oxaloacetic acid in scurvy. J. Biol. Chem. 284, 3094-3096 (1959). 

Table II shows solvent effects in the asymmetric synthesis of alanine from pyruvic acid and (S)-a-methylbenzylamine( ). The optical purity of alanine decreases with increasing polarity of the solvent. In the case of the asymmetric synthesis of glutamic acid from a-keto glutaric acid and (S)-a-methylbenzylcimine, the configuration of the resulting glutamic acid was actually inverted by the use of polar solvents. The substrate appears to interact with the catalyst more strongly in a less polar than in a more polar solvent. Thus, the population of the chelated substrate is...

Important information can be obtained from the electrophoretic mobility at different pH values regarding the acidic and basic groups present in the molecule. Thus, no change is observed in the mobility for acid amides between pH 6.5 and 2.0, weak acids as succinic acid will be protonated completely at pH 3.0 (loss of a negative charge as compared with pH 6.5) while a-keto glutaric acid will be protonated completely only at pH 2.0 (cf. Section 2.3) (refs. 18, 19). 

The amino group of the chromophore (1) is substituted amidically by small dibasic acids which all stem from the glutamic acid metabolism. In addition to the latter (ref. 20) succinic acid and its amide (refs. 18-21), malic acid (ref. 22) and a-keto glutaric acid (refs. 18-20) have been encountered (succinic acid seems to be an artefact stemming either from its amide or from a-keto glutaric acid). The mass of the acid present in the molecule can be deduced from a characteristic retro-Diels-Alder fragment of the quinoline nucleus in the FAB spectra of the free ligands (see m/z 985 in Fig. 1). 

With the exception of a-keto glutaric acid the acids can be identified after total hydrolysis together with the amino acids. A distinction between succinic acid and its amide is possible by reduction with NaBH4 after esterification Only the ester will be reduced to y hydroxy butyric acid which can be identified as r-butyrolactone (ref. 18). 

Otani, T. T., and A. Meister co-Amide and co-amino acid derivatives of a-keto-glutaric acid and oxalacetic acid. J. Biol. Chem. 224, 137 (1957). 

The excessive pyruvate accumulation might be due to the coincident measurement of alpha-keto glutaric acid when the nonchromatographio techniques are used this is perhaps the case in the psychotic patients, at least since we observed a rise in alpha-keto-glutaric acid rather than the normal fall after glucose by mouth. 

Decreases in fasting true blood glucose and in blood lactic, pyruvic, citric, and perhaps alpha-keto glutaric acid concentrations occur after the intravenous infusion of large amounts of GSH in normal and psychotic subjects. This effect is not due to anxiety or stress in the fasting state in... 

In addition to acetaldehyde, molecules present in grape juice that react with bisulhte are pyruvic acid, a-keto-glutaric acid, dihydroxyacetone, diacetyl, anthocyanin pigments, and others (Ough, 1993b). 

The glutamic acid can enter the tricarboxylic acid cycle through a-keto-glutaric acid, so histidine is thus degraded to COg and water. 

Chernyavskaya OG, Shishkanova NV, Il chenko AP, Finogenova TV (2000) Synthesis of a-keto-glutaric acid by Yarrowia lipolytica yeast grown on ethanol. Appl Microbiol Biotechnol... 

Dogra J V V, Sinha S K P 1979 Observations on the age related changes in the level of a-keto-glutaric acid in leaves of Phyllanthus simplex (Retz.). Comp Physiol Ecol 4 35-37... 

An enzyme that transaminates y-aminobutyric acid has been shown to occur in brain and liver [IS, 14). The amino group acceptor is a-keto-glutaric acid and the reaction products are succinic semialdehyde and... 

III. The concentrations of succinic, malic, oxalacetic, citric, and o-keto-glutaric acids are of the order of 1 to 2 X 10 M in liver and kidney, that of fumaric acid about 7 X 10 M. The concentrations are in general somewhat higher in brain and lower in muscle. Noteworthy is the relatively high concentration of a-ketoglutarate and oxalacetate in brain. 

Trans-amination requires a specific amino donor, glutamic, or aspartic acid, or a specific amino acceptor, a-keto-glutaric acid, or oxaloacetic acid, according to the direction of the reaction. 

The amino group of the mono-carboxylic amino acids is transferred to keto-glutaric acid, and the glutamic acid thus formed is readily deaminated in the tissue. 

Alanine is a precursor of glucose in the diabetic animal, and also is a non-essential acid. It is significant, however, in being related in strueture, though not necessarily in biological derivation, to many more complex and important amino acids, and it readily trans-aminates with keto-glutaric acid. 

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