All Photos(3)

K0629

Sigma-Aldrich

Sodium 4-methyl-2-oxovalerate

leucine metabolite

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

Quality Level

assay

>98% (TLC)

form

powder

application(s)

HPLC: suitable
cell analysis: suitable

color

white to off-white

mp

275 °C (dec.) (lit.)

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.

Packaging

1, 5 g in poly bottle

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.

Storage Class Code

13 - Non 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

Certificate of Analysis

Certificate of Origin

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)
Branched chain a- Keto acid metabolism
JOE A. BOWDEN
The Journal of Biological Chemistry, 243, 3526-3531 (1968)
Analysis of Branched-Chain Keto Acids in Cell Extracts by HPLC-Fluorescence Detention
Ayuna HATTORI
Chromatography, 38, 129-133 (2017)
Yuhong Zhu et al.
Enzyme and microbial technology, 49(4), 321-325 (2011-11-25)
This work aims to produce α-ketoisocaproate (KIC) from L-leucine via the free-whole-cell biotransformation of Rhodococcus opacus DSM 43250. The effects of temperature, pH, substrate concentration, cell concentration, and rotating speed on KIC production were examined. Furthermore, the biotransformation conditions were...

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