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11-SEPTEMBER-2008 13:54:10 - ketoglutaric acid Redirected from Alpha-ketoglutarate Alpha-ketoglutaric acid IUPAC name 2-Oxopentanedioic acid Other names 2-Ketoglutaric acid alpha-Ketoglutaric acid 2-Oxoglutarate 2-Oxoglutaric acid Oxoglutaric acid Identifiers CAS number 328-50-7 PubChem 51 MeSH alpha-ketoglutaric+acid SMILES OC=OCCC=OCO=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 references 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. Contents 1 Functions 1.1 Krebs cycle 1.2 Formation of amino acids 1.3 Nitrogen transporter 1.4 Relationship to molecular oxygen 1.5 Dietary supplement 2 Production 3 References 4 External links 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, 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. Alpha-ketoglutarate can be used to produce: Creatine-alpha ketoglutarate References Merck Index, 13th ion, 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 + ATPGTP Pi + ADPGDP + H2O NADH + H+ + CO2 CoA NAD+ H2O H2O NADP+ NADPH + H+ CO2 Citrate cis-Aconitate Isocitrate Oxalosuccinate α-Ketoglutarate Retrieved from http://en..org/wiki/Alpha-ketoglutaric_acid Categories: Citric acid cycle | Ketones | Dicarboxylic acids | Citric acid cycle compounds Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Česky Dansk Deutsch Italiano Magyar 日本語 Português Svenska This page was last modified on 1 July 2008, at 12:36
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