Alpha-ketoglutaric acid

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Alpha-ketoglutaric acid
IUPAC name	2-Oxopentanedioic acid
Other names	2-Ketoglutaric acid alpha-Ketoglutaric acid 2-Oxoglutamate 2-Oxoglutaric acid Oxoglutaric acid
Identifiers
CAS number	328-50-7
PubChem	51
MeSH	alpha-ketoglutaric+acid
SMILES	OC(=O)CCC(=O)C(O)=O
Properties
Molecular formula	C5H6O5
Molar mass	146.11 g/mol
Melting point	113.5
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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Overview

Alpha-ketoglutaric acid is one of two ketone derivatives of glutaric acid. (The term "ketoglutaric acid," when not further qualified, almost always refers to the alpha variant. Beta-ketoglutaric acid varies only by the position of the ketone functional group, and is much less common.)

Its anion, Alpha-ketoglutarate (also called oxo-glutarate) is an important biological compound. It is the keto acid produced by de-amination of glutamate, and is an intermediate in the Krebs cycle.

Functions

Krebs cycle

It is a key intermediate in the Krebs cycle, coming after isocitrate and before succinyl CoA. Anaplerotic reactions can replenish the cycle at this juncture by synthesizing alpha-ketoglutarate from transamination of glutamate, or through action of glutamate dehydrogenase on glutamate.

Formation of amino acids

Glutamine is synthesized from glutamate by glutamine synthase, which utilizes an ATP to form glutamyl phosphate; this intermediate is attacked by ammonia as a nucleophile giving glutamine and inorganic phosphate.

Nitrogen transporter

Another function is to combine with nitrogen released in the cell, therefore preventing nitrogen overload.

Alpha-ketoglutarate is one of the most important nitrogen transporter in metabolic pathways. The amino groups of amino acids are attached to it by transamination and carried to the liver where the urea cycle takes place.

Alpha-ketoglutarate is transaminated, along with glutamine, to form the excitatory neurotransmitter glutamate. Glutamate can then be decarboxylated (requiring vitamin B₆) into the inhibitory neurotransmitter GABA.

It is reported that high ammonia and/or high nitrogen levels may occur with high protein intake, excessive aluminum exposure, autism, Reye's syndrome, cirrhosis, and urea cycle disorder.

Relationship to molecular oxygen

Acting as a co-substrate, it also plays important function in oxidation reactions involving molecular oxygen.

Molecular oxygen (O₂) directly oxidizes many compounds to produce useful products in an organism, such as antibiotics, etc., in reactions catalyzed by oxygenases. In many oxygenases, alpha-ketoglutarate helps the reaction by being oxidized together with the main substrate. In fact, one of the alpha-ketoglutarate-dependent oxygenases is an O₂ sensor, informing the organism the oxygen level in its environment.

Dietary supplement

Alpha-ketoglutaric acid is sold as a dietary supplement and to body builders as AKG or a-KG. Some believe it increases stamina.

Production

Alpha-ketoglutarate can be produced by

• Oxidative decarboxylation of isocitrate by isocitrate dehydrogenase;
• Oxidative deamination of glutamate by glutamate dehydrogenase.

References

Merck Index, 13th Edition, 5320.

External links

v • d • e Citric Acid Cycle Metabolic Pathway
Oxaloacetate Malate Fumarate Succinate Succinyl-CoA Acetyl-CoA NADH + H+ NAD+ H2O FADH2 FAD CoA + ATP(GTP) Pi + ADP(GDP) + H2O NADH + H+ + CO2 CoA NAD+ H2O H2O NAD(P)+ NAD(P)H + H+ CO2 Citrate cis-Aconitate Isocitrate Oxalosuccinate α-Ketoglutarate

da:Αlfa-ketoglutarat

de:Α-Ketoglutarsäure it:Acido 2-chetoglutarico hu:Alfa-ketoglutársavsv:Alfa-ketoglutarsyra

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .