α-Ketoglutaric acid

α-Ketoglutaric acid^[1]

Names
Preferred IUPAC name 2-Oxopentanedioic acid
Other names 2-Ketoglutaric acid alpha-Ketoglutaric acid 2-Oxoglutaric acid Oxoglutaric acid
Identifiers
CAS Number	328-50-7 Y
3D model ( JSmol )	Interactive image
ChEBI	CHEBI:30915 Y
ChemSpider	50 Y
DrugBank	DB02926 N
ECHA InfoCard	100.005.756
IUPHAR/BPS	3636
KEGG	C00026 Y
MeSH	alpha-ketoglutaric+acid
PubChem CID	51
UNII	8ID597Z82X Y
CompTox Dashboard (EPA)	DTXSID5033179
InChI InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) Y Key: KPGXRSRHYNQIFN-UHFFFAOYSA-N Y InChI=1/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10) Key: KPGXRSRHYNQIFN-UHFFFAOYAN
SMILES O=C(O)C(=O)CCC(=O)O
Properties
Chemical formula	C5H6O5
Molar mass	146.098 g·mol−1
Melting point	115 °C (239 °F; 388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

α-Ketoglutaric acid (2-oxoglutaric acid) is a keto acid.

Its

The term "ketoglutaric acid", when not further qualified, almost always refers to the alpha variant. β-Ketoglutaric acid varies only by the position of the ketone functional group, and is much less common.

Functions

Alanine transaminase

The enzyme

Glutamine is synthesized from glutamate by glutamine synthetase, which utilizes adenosine triphosphate to form glutamyl phosphate; this intermediate is attacked by ammonia as a nucleophile giving glutamine and inorganic phosphate. Proline, arginine, and lysine (in some organisms) are other amino acids synthesized as well.^[2] These three amino acids derive from glutamate with the addition of further steps or enzymes to facilitate reactions.^[3]

Nitrogen transporter

Another function is to combine with nitrogen released in cells, therefore preventing nitrogen overload.^[4]

α-Ketoglutarate is one of the most important nitrogen transporters 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.^[5]

α-Ketoglutarate is transaminated, along with glutamine, to form the excitatory

It plays a role in detoxification of ammonia in brain.^[8][9][10]

Relationship to molecular oxygen

Acting as a co-substrate for

Studies have linked α-ketoglutarate with increased lifespan in nematode worms^[12] and increased healthspan/lifespan in mice.^[13][14][15]

Immune regulation

A study showed that in glutamine deprived conditions, α-ketoglutarate promotes

α-Ketoglutarate has been shown to be a cofactor for demethylases that contain the Jumonji C (JmjC) domain.^[17][18]

Production

α-Ketoglutarate can be produced by:

• isocitrate by isocitrate dehydrogenase
• glutamate by glutamate dehydrogenase
• From
  galacturonic acid by the organism Agrobacterium tumefaciens^[19]

• Creatine-alpha ketoglutarate

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

[[File:

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

|alt=TCACycle_WP78 edit]]

TCACycle_WP78 edit

1. ^ The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

See also

• 2OG-dependent dioxygenases

References