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Information about Alpha Ketoglutarate

Alpha-ketoglutaric acid
IUPAC name2-Oxopentanedioic acid
Other names2-Ketoglutaric acid
alpha-Ketoglutaric acid
2-Oxoglutamate
2-Oxoglutaric acid
Oxoglutaric acid
Identifiers
CAS number328-50-7
PubChem51
MeSHalpha-ketoglutaric+acid
SMILESOC(=O)CCC(=O)C(O)=O
style="background: #F8EABA; text-align: center;" colspan="2" Melting point 113.5
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)
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, an 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.

Formation of amino acids

One of its functions is to combine with ammonia to form glutamic acid and then glutamine.

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

References

Merck Index, 13th Edition, 5320.

External links

 •  • [ e]
Citric Acid Cycle Metabolic Pathway
OxaloacetateMalateFumarateSuccinateSuccinyl-CoA
Acetyl-CoANADH + H+NAD+H2OFADH2FADCoA + ATP(GTP)Pi + ADP(GDP)
+H2ONADH + H+ + CO2
CoANAD+
H2OH2ONAD(P)+NAD(P)H + H+CO2
Citratecis-AconitateIsocitrateOxalosuccinateα-Ketoglutarate
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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PubChem is a database of chemical molecules. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH).
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Medical Subject Headings (MeSH) is a huge controlled vocabulary (or metadata system) for the purpose of indexing journal articles and books in the life sciences. Created and updated by the United States National Library of Medicine (NLM), it is used by the MEDLINE/PubMed
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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A ketone (pronounced as key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group.
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Glutaric acid (IUPAC systematic name: pentanedioic acid) is a simple five-carbon linear dicarboxylic acid.

Synonyms

  • 1,3-Propanedicarboxylic acid
  • Pentanedioic acid
  • propane-1,3-dicarboxylic acid
  • n-Pyrotartaric acid

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In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules.
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Keto acids are organic acids containing a ketone functional group and a carboxylic acid group.

Common types of keto acids include:
  • Alpha-keto acids, or 2-oxo acids, such as pyruvic acid have the keto group adjacent to the carboxylic acid

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Glutamic acid or glutamate (abbreviated as Glu or E; Glx or Z represents either glutamic acid or glutamine), is the protonated form of glutamate (the anion). Glutamate is one of the 20 proteinogenic amino acids.
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citric acid cycle, also known as the tricarboxylic acid (TCA) cycle, the Krebs cycle, or Szent-Györgyi-Krebs cycle (after Hans Adolf Krebs and Albert Szent-Györgyi who first determined the chemical intermediates and reaction sequence of the cycle), is a series
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citric acid cycle, also known as the tricarboxylic acid (TCA) cycle, the Krebs cycle, or Szent-Györgyi-Krebs cycle (after Hans Adolf Krebs and Albert Szent-Györgyi who first determined the chemical intermediates and reaction sequence of the cycle), is a series
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Isocitric acid is a protonated form of isocitrate, which is a substrate of the citric acid cycle. Isocitrate is formed from citrate with the help of the enzyme aconitase, and is acted upon by isocitrate dehydrogenase.
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Succinyl-Coenzyme A, generally abbreviated as Succinyl-CoA or SucCoA is a combination of succinic acid and coenzyme A.

Source

It is an important intermediate in the citric acid cycle, where it is synthesized from α-Ketoglutarate by
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Anaplerotic reactions are those that form intermediates of the TCA or citric acid cycle. The malate is created by PEP carboxylase and malate dehydrogenase in the cytosol. Malate, in the mitochondrial matrix, can be used to make pyruvate (catalyzed by NAD+ malic enzyme) or
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Glutamic acid or glutamate (abbreviated as Glu or E; Glx or Z represents either glutamic acid or glutamine), is the protonated form of glutamate (the anion). Glutamate is one of the 20 proteinogenic amino acids.
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Glutamine (abbreviated as Gln or Q; Glx or Z represents either glutamine or glutamic acid) is one of the 20 amino acids encoded by the standard genetic code.
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Transamination (or aminotransfer) is the reaction between an amino acid and an alpha-keto acid. The amino group is transferred from the former to the latter; this results in the amino acid being converted to the corresponding α-keto acid, while the reactant α-keto acid is
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The urea cycle (also known as the ornithine cycle) is a cycle of biochemical reactions occurring in many animals that produces urea from ammonia (NH3). This cycle was the first metabolic cycle discovered (Krebs and Kurt Henseleit, 1932).
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Neurotransmitters are chemicals that are used to relay, amplify and modulate signals between a neuron and another cell. According to the prevailing beliefs of the 1960s, a chemical can be classified as a neurotransmitter if it meets the following conditions:

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Glutamic acid or glutamate (abbreviated as Glu or E; Glx or Z represents either glutamic acid or glutamine), is the protonated form of glutamate (the anion). Glutamate is one of the 20 proteinogenic amino acids.
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Vitamin B6 is a water-soluble vitamin. Pyridoxal phosphate (PLP) is the active form and is a cofactor in many reactions of amino acid metabolism, including transamination, deamination, and decarboxylation.
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Gaba may refer to:
  • GABA, the gamma-aminobutyric acid neurotransmitter
  • GABA receptor, in biology, receptors with GABA as their endogenous ligand
  • Gabâ or gabaa (Philippines), the concept of negative karma of the Cebuano people

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Proteins are large organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid residues.
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Autism
Classification & external resources

Obsessively stacking or lining up objects may indicate autism.
ICD-10 F 84.0
ICD-9 299.0

OMIM 209850
DiseasesDB 1142
MedlinePlus 001526
eMedicine med/3202   ped/180
MeSH D001321
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Reye's syndrome
Classification & external resources

ICD-10 G 93.7
ICD-9 331.81

DiseasesDB 11463
MedlinePlus 001565
eMedicine emerg/399  

MeSH C06.552.241.
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MeSH D008103 Cirrhosis is a consequence of chronic liver disease characterized by replacement of liver tissue by fibrotic scar tissue as well as regenerative nodules, leading to progressive loss of liver function.
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urea cycle disorder or urea cycle defect is a genetic disorder caused by a deficiency of one of the enzymes in the urea cycle which is responsible for removing ammonia from the blood stream.
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