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K1128

Sigma-Aldrich

αAcide α-cétoglutarique

BioReagent, suitable for cell culture, suitable for insect cell culture

Synonyme(s) :

Acide 2-oxoglutarique, Acide 2-oxopentanedioïque

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About This Item

Formule linéaire :
HOOCCH2CH2COCOOH
Numéro CAS:
328-50-7
Poids moléculaire :
146.10
Numéro Beilstein :
1705689
Numéro CE :
206-330-3
Numéro MDL:
MFCD00004165
Code UNSPSC :
12352204
ID de substance PubChem :
24896202
Nomenclature NACRES :
NA.32

Gamme de produits

BioReagent

Niveau de qualité

200

Pureté

≥98.5% NaOH basis (titration)

Forme

powder or crystals

Technique(s)

cell culture | insect: suitable
cell culture | mammalian: suitable

Solubilité

water: 100 mg/mL, clear to slightly hazy, colorless to almost colorless

Température de stockage

2-8°C

Chaîne SMILES 

OC(=O)CCC(=O)C(O)=O

InChI

1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

Clé InChI

KPGXRSRHYNQIFN-UHFFFAOYSA-N

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Description générale

Alpha-ketoglutarate (αKG), a vital intermediate in the tricarboxylic acid (TCA)/Krebs cycle, is located between succinyl-CoA and isocitrate.

Application

α-Ketoglutaric acid has been used:
  • as a supplement in minimum essential medium α (α-MEM) to culture primary mesenchymal stromal/stem cells (MSCs) to study its effects on age-related osteoporosis
  • for chemical treatments to compare the treatment effects of several compounds on lifespan between manual and automated lifespan machine (ALM) platforms
  • as a printed chemotaxis ligand to screen chemotaxis receptors with high-throughput technologies and verify the interactions with surface plasmon resonance (SPR)

Actions biochimiques/physiologiques

Alpha-ketoglutarate (αKG), a nitrogen scavenger, is an important source of glutamate and glutamine. It controls the synthesis of ATP and decreases the generation of equivalent (NAD+/NADH) in the tricarboxylic acid (TCA) cycle. It promotes the synthesis of protein and prevents protein degradation in muscles. This immune nutrient factor participates in the general immune and collagen metabolism. In aged rodents, αKG accelerates the healing of bone defects. It may possess potential anti-aging effects. This Krebs cycle molecule can be used as a supplement in insect and mammalian cell cultures.

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H318

Classification des risques

Eye Dam. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Nan Wu et al.
Biomolecules & therapeutics, 24(1), 1-8 (2016-01-14)
Alpha-ketoglutarate (AKG) is a key molecule in the Krebs cycle determining the overall rate of the citric acid cycle of the organism. It is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits
J Kitaura et al.
European journal of pediatrics, 158(5), 410-413 (1999-05-20)
Two cases of hyperinsulinaemic hypoglycaemia associated with persistent hyperammonaemia in unrelated infants of 7 days and 4 months of age are reported. Blood ammonia levels were 100-300 micromol/l (normal values <40 micromol/l). The hyperammonaemia was asymptomatic and not associated with
F Rocchiccioli et al.
Biomedical mass spectrometry, 11(1), 24-28 (1984-01-01)
Quantification of 2-ketoglutaric acid in plasma and cerebrospinal fluid as its O-trimethylsilyl++-quinoxalinol derivative by gas chromatography chemical ionization mass spectrometry is described with benzoylformic acid as internal standard. This technique, with ammonia as reactant gas, only detects the protonated molecular
Agata M Pudlik et al.
Applied and environmental microbiology, 79(4), 1095-1101 (2012-12-04)
Transamination is the first step in the conversion of amino acids into aroma compounds by lactic acid bacteria (LAB) used in food fermentations. The process is limited by the availability of α-ketoglutarate, which is the best α-keto donor for transaminases
Ivanhoe K H Leung et al.
Journal of medicinal chemistry, 56(2), 547-555 (2012-12-14)
The human 2-oxoglutarate (2OG) dependent oxygenases belong to a family of structurally related enzymes that play important roles in many biological processes. We report that competition-based NMR methods, using 2OG as a reporter ligand, can be used for quantitative and
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