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K1128

Sigma-Aldrich

α-Ketoglutaric acid

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

Synonym(s):

2-Oxoglutaric acid, 2-Oxopentanedioic acid

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About This Item

Linear Formula:
HOOCCH2CH2COCOOH
CAS Number:
328-50-7
Molecular Weight:
146.10
Beilstein/REAXYS Number:
1705689
EC Number:
206-330-3
MDL number:
MFCD00004165
UNSPSC Code:
12352204
PubChem Substance ID:
24896202
NACRES:
NA.32

product line

BioReagent

Quality Level

200

assay

≥98.5% NaOH basis (titration)

form

powder or crystals

technique(s)

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

solubility

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

storage temp.

2-8°C

SMILES string

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)

InChI key

KPGXRSRHYNQIFN-UHFFFAOYSA-N

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General description

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)

Biochem/physiol Actions

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.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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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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