D-α-Hydroxyglutaric acid

D-α-Hydroxyglutaric acid ((R) -2-Hydroxyglutarate) is the principal metabolite accumulating in neurometabolic disease D-2-hydroxyglutaric aciduria. D-α-Hydroxyglutaric acid is a weak competitive antagonist of α-ketoglutarate (α-KG) and inhibits multiple α-KG-dependent dioxygenases with a Ki of 10.87 mM. D-α-Hydroxyglutaric acid increases reactive oxygen species (ROS) production. D-α-Hydroxyglutaric acid binds and inhibits ATP synthase and inhibits mTOR signaling[1][2][3][4][5].

Product Specifications

CAS Number

[13095-47-1]

Product Name Alternative

(R) -2-Hydroxyglutarate; (R) -2-Hydroxyglutaric acid; (R) -2-Hydroxypentanedioic acid

UNSPSC

12352211

Hazard Statement

H302, H312, H332

Target

ATP Synthase; Endogenous Metabolite; mTOR; Reactive Oxygen Species (ROS)

Type

Natural Products

Related Pathways

Immunology/Inflammation; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; NF-κB; PI3K/Akt/mTOR

Applications

COVID-19-immunoregulation

Field of Research

Cancer; Inflammation/Immunology; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/d-α-hydroxyglutaric-acid.html

Purity

98.0

Solubility

DMSO : 100 mg/mL|H2O : 200 mg/mL (ultrasonic)

Smiles

O=C(O)[C@H](O)CCC(O)=O

Molecular Formula

C5H8O5

Molecular Weight

148.11

Precautions

H302, H312, H332

References & Citations

[1]Xu W, et al. Oncometabolite 2-hydroxyglutarate is a competitive inhibitor of α-ketoglutarate-dependent dioxygenases. Cancer Cell. 2011 Jan 18;19 (1) :17-30.|[2]Fu X, et al. 2-Hydroxyglutarate Inhibits ATP Synthase and mTOR Signaling. Cell Metab. 2015 Sep 1;22 (3) :508-15.|[3]Martijn Kranendijk, et al. Progress in understanding 2-hydroxyglutaric acidurias. J Inherit Metab Dis. 2012 Jul;35 (4) :571-87.|[4]Martin Böttcher, et al. D-2-hydroxyglutarate interferes with HIF-1α stability skewing T-cell metabolism towards oxidative phosphorylation and impairing Th17 polarization. Oncoimmunology. 2018 Mar 26;7 (7) :e1445454.|[5]Alexandra Latini , et al. D-2-hydroxyglutaric acid induces oxidative stress in cerebral cortex of young rats. Eur J Neurosci. 2003 May;17 (10) :2017-22.