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Ketoglutaric acid
From Wikipedia, the free encyclopedia
| Ketoglutaric acid | |
|---|---|
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| IUPAC name | 2-Oxopentanedioic acid |
| Other names | 2-Ketoglutaric acid alpha-Ketoglutaric acid 2-Oxoglutamate 2-Oxoglutaric acid Oxoglutaric acid |
| Identifiers | |
| CAS number | [] |
| PubChem | |
| MeSH | |
| SMILES | OC(C(CCC(O)=O)=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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Ketoglutaric acid is refers to either of two crystalline ketone derivatives of glutaric acid which differ only by the position of the ketone functional group. Beta-ketoglutaric acid is much less common.
Its anion, Alpha-ketoglutarate is an important biological compound and is a key intermediate in the Krebs cycle. Alpha-ketoglutarate occurs naturally within cells. One of its functions is to combine with ammonia to form glutamic acid and then glutamine. Another function is to combine with nitrogen released in the cell, therefore preventing nitrogen overload. Acting as a cosubstrate, it also plays important function in oxidation reactions involving molecular oxygen.
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. Glumate 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 & urea cycle disorder.
Molecular oxygen (O2) directly oxidizes many compounds to produce useful products in an organism, such as antibiotics ect, in reactions catalized 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.
Alpha-ketoglutaric acid is sold as a dietary supplement and to body builders as AKG or a-KG. Some believe it increases stamina.
Alpha-ketoglutarate can be produced by
- Oxidative decarboxylation of isocitrate by isocitrate dehydrogenase;
- Oxidative deamination of glutamate by glutamate dehydrogenase.
Merck Index, 13th Edition, 5320.
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