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Sigma-Aldrich

L-α-Hydroxyglutaric acid disodium salt

≥98.0% (GC)

Synonym(s):

(S)-2-Hydroxypentanedioic acid disodium salt, Disodium (S)-2-hydroxyglutarate

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About This Item

Linear Formula:
C5H6O5Na2
CAS Number:
63512-50-5
Molecular Weight:
192.08
Beilstein/REAXYS Number:
5318042
MDL number:
MFCD00021700
UNSPSC Code:
12352106
PubChem Substance ID:
329769949
NACRES:
NA.32

Quality Level

100

assay

≥98.0% (GC)

form

powder or crystals

optical activity

[α]/D -8.5±1.5°, c = 1 in 0.1 M NaOH

impurities

≤6.0% water

relevant disease(s)

cancer

storage temp.

2-8°C

SMILES string

[O-]C(CC[C@@H](C([O-])=O)O)=O.[Na+].[Na+]

InChI

1S/C5H8O5.2Na/c6-3(5(9)10)1-2-4(7)8;;/h3,6H,1-2H2,(H,7,8)(H,9,10);;/q;2*+1/p-2/t3-;;/m0../s1

InChI key

DZHFTEDSQFPDPP-QTNFYWBSSA-L

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General description

Glutamic acid is metabolized to α-Hydroxyglutaric acid in an NAD-dependent manner by cell-free extracts of Peptococcus aerogenes. It is formed as an intermediate during glyoxylic acid metabolism in bacteria.

Application

L-α-Hydroxyglutaric acid disodium salt is suitable for use in collection buffer for increased recovery of hypoxia-inducible factor-1 α (HIF-1α), a marker of hypoxia in human tumors. It is also suitable for the radiolabeled 5mC-5hmC conversion assay to study the effect of 2-HG on the TET family of methyl hydroxylases.

Biochem/physiol Actions

L-alpha-Hydroxyglutaric acid accumulates as a result of a rare defect in L-2-HG dehydogenase, leading to the metabolic disorder L-2-hydroxyglutaric aciduria (L-2HGA). L-2HGA is associated with neuronal defects, leukodystrophy and linked to an increased risk of brain tumors.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The production of alpha-hydroxyglutaric acid from glutamic acid by cell-free preparations of Peptococcus aerogenes.
W M Johnson et al.
Canadian journal of biochemistry, 47(12), 1103-1107 (1969-12-01)
Hugh Colvin et al.
Scientific reports, 6, 36289-36289 (2016-11-09)
Deranged metabolism is a hallmark of cancer, playing a significant role in driving the disease process. One such example is the induction of carcinogenesis by the oncometabolite D-2 hydroxyglutarate (D-2HG), which is produced by the mutated enzyme isocitrate dehydrogenase (IDH)
Rapid separation of some common intermediates of microbial metabolism by thin-layer chromatography.
A S Bleiweis et al.
Analytical biochemistry, 20(2), 335-338 (1967-08-01)
A S Bleiweis et al.
Journal of bacteriology, 94(5), 1560-1564 (1967-11-01)
Aspergillus glaucus, cultured on sodium propionate-mineral salts medium, incorporates (14)C-glyoxylate into labeled alpha-hydroxyglutaric acid within 30 sec. Mycelial extracts retain this biosynthetic capacity, which is destroyed by heating. Propionyl-2-(14)C-coenzyme A also in incorporated into labeled alpha-hydroxyglutaric acid by these mycelial
Peppi Koivunen et al.
Nature, 483(7390), 484-488 (2012-02-22)
The identification of succinate dehydrogenase (SDH), fumarate hydratase (FH) and isocitrate dehydrogenase (IDH) mutations in human cancers has rekindled the idea that altered cellular metabolism can transform cells. Inactivating SDH and FH mutations cause the accumulation of succinate and fumarate
View All Related Papers

Protocols

Chiral LC-MS/MS of D- and L-2-Hydroxyglutaric Acid Biomarkers

We describe here a rapid and sensitive method to separate and measure D-2-OHG and L-2-OHG enantiomers using high-resolution mass spectrometry (HRMS) detection.

Chromatograms

application for HPLCapplication for HPLC

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