α-Hydroxyglutaric acid

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α-Hydroxyglutaric acid
File:Alpha-hydroxyglutaric acid.png
Names
Preferred IUPAC name
2-Hydroxypentanedioic acid
Other names
2-Hydroxyglutaric acid
Identifiers
3D model (JSmol)
1723805
ChEBI
ChemSpider
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KEGG
MeSH Alpha-hydroxyglutarate
UNII
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  • InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10) checkY
    Key: HWXBTNAVRSUOJR-UHFFFAOYSA-N checkY
  • InChI=1/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)
    Key: HWXBTNAVRSUOJR-UHFFFAOYAI
  • C(CC(=O)O)C(C(=O)O)O
  • O=C(O)C(O)CCC(=O)O
Properties
C5H8O5
Molar mass 148.114 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

α-Hydroxyglutaric acid (2-hydroxyglutaric acid) is an alpha hydroxy acid form of glutaric acid.

In biology

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In humans the compound is formed by a hydroxyacid-oxoacid transhydrogenase whereas in bacteria is formed by a 2-hydroxyglutarate synthase. The compound can be converted to α-ketoglutaric acid through the action of a 2-hydroxyglutarate dehydrogenase which, in humans, are two enzymes called D2HGDH and L2HGDH. Deficiency in either of these two enzymes lead to a disease known as 2-hydroxyglutaric aciduria.

D-2-hydroxyglutarate

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Mutations in isocitrate dehydrogenase (IDH1 and IDH2), which frequently occur in glioma and AML,[1][2][3] produce D-2-hydroxyglutarate from alpha-ketoglutarate.[4] D-2-hydroxyglutarate accumulates to very high concentrations which inhibits the function of enzymes that are dependent on alpha-ketoglutarate, including histone lysine demethylases.[5][6] This leads to a hypermethylated state of DNA and histones,[7] which results in different gene expression that can activate oncogenes and inactivate tumor-suppressor genes. Studies have also shown that 2-hydroxyglutarate may be converted back to alpha-ketoglutarate either enzymatically or non-enzymatically.[8][9] Further studies are required to fully understand the dynamics between 2-hydroxyglutarate and alpha-ketoglutarate.

L-2-hydroxyglutarate

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On the other hand, L-2-hydroxyglutarate is produced at high levels in low oxygen conditions, including cells of the immune system.[10]

References

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