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90790

Sigma-Aldrich

L-α-Hydroxyglutaric acid disodium salt

≥98.0% (GC)

Sinónimos:

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

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About This Item

Fórmula lineal:
C5H6O5Na2
Número de CAS:
63512-50-5
Peso molecular:
192.08
Beilstein:
5318042
Número MDL:
MFCD00021700
Código UNSPSC:
12352106
ID de la sustancia en PubChem:
329769949
NACRES:
NA.32

Análisis

≥98.0% (GC)

formulario

powder or crystals

actividad óptica

[α]/D -8.5±1.5°, c = 1 in 0.1 M NaOH

impurezas

≤6.0% water

enfermedades relevantes

cancer

temp. de almacenamiento

2-8°C

cadena SMILES

[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

Clave InChI

DZHFTEDSQFPDPP-QTNFYWBSSA-L

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Descripción general

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.

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «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
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Protocolos

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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