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K0629

Sigma-Aldrich

Sodium 4-methyl-2-oxovalerate

leucine metabolite

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Synonym(s):
α-Ketoisocaproic acid sodium salt, 4-Methyl-2-oxopentanoic acid sodium salt, 4-Methyl-2-oxovaleric acid sodium salt, Ketoleucine sodium salt
Linear Formula:
(CH3)2CHCH2COCOONa
CAS Number:
4502-00-5
Molecular Weight:
152.12
Beilstein:
4239297
EC Number:
224-816-3
MDL number:
MFCD00064193
PubChem Substance ID:
24896196
NACRES:
NA.25

Quality Level

100

Assay

>98% (TLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

mp

275 °C (dec.) (lit.)

application(s)

cell analysis

storage temp.

2-8°C

SMILES string

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

InChI

1S/C6H10O3.Na/c1-4(2)3-5(7)6(8)9;/h4H,3H2,1-2H3,(H,8,9);/q;+1/p-1

InChI key

IXFAZKRLPPMQEO-UHFFFAOYSA-M

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Application

Sodium 4-methyl-2-oxovalerate has been used for quantifying branched-chain keto acids from cell extracts by HPLC-fluorescence method.

Biochem/physiol Actions

α-Ketoisocaproic acid is a leucine metabolite that is known to induce insulin secretion from the βcells of pancreas. Enteral infusion of aα-Ketoisocaproate is found to ameliorate, endotoxemic condition. The resulting ketone bodies obtained from its conversion, might serve as an energy source. Accumulation of α-Ketoisocaproic acid is characterized in branched chain ketoaciduria, which is caused due to the lack of branched chain L-2-keto acid dehydrogenase activity. α-Ketoisocaproic acid causes dissociation in the oxidative phosphorylation reaction and acts as a metabolic inhibitor of α-ketoglutarate dehydrogenase. Thus, leads to a defect in the mitochondrial homeostasis, observed in branched chain ketoaciduria.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Enteral infusion of sodium 2-ketoisocaproate in endotoxic rats.
Hirokawa M and Walser M
Critical Care Medicine, 27(2), 373-379 (1999)
Effects of L-leucine and alpha-ketoisocaproic acid upon insulin secretion and metabolism of isolated pancreatic islets.
Panten U
Febs Letters, 20(2), 225-228 (1972)
Analysis of Branched-Chain Keto Acids in Cell Extracts by HPLC-Fluorescence Detention
Ayuna HATTORI
Chromatography, 38, 129-133 (2017)
Branched chain a- Keto acid metabolism
JOE A. BOWDEN
The Journal of Biological Chemistry, 243, 3526-3531 (1968)
Chung-De Chen et al.
Journal of bacteriology, 194(22), 6206-6216 (2012-09-18)
Branched-chain aminotransferases (BCAT), which utilize pyridoxal 5'-phosphate (PLP) as a cofactor, reversibly catalyze the transfer of the α-amino groups of three of the most hydrophobic branched-chain amino acids (BCAA), leucine, isoleucine, and valine, to α-ketoglutarate to form the respective branched-chain
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