4502-00-5 Usage
Description
Sodium ketoisocaproate, also known as 4-methyl-2-oxovalerate, is an α-ketomonocarboxylic acid that plays a significant role in the metabolism of leucine and is found in various food sources such as banana, asparagus, cheese, white wine, cocoa, blue cheese, and provolone cheese. It has the chemical formula C6H11NaO3 and is known for its ability to trigger insulin release by acting on receptor sites that differ from those occupied by amino acids.
Uses
Used in Analytical Chemistry:
Sodium ketoisocaproate is used as a quantification agent for branched-chain keto acids from cell extracts in the high-performance liquid chromatography-fluorescence (HPLC-fluorescence) method. This application is crucial for the accurate measurement and analysis of these acids in various biological samples.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Sodium ketoisocaproate is used as an intermediate in the metabolism of leucine, an essential branched-chain amino acid. Its role in the metabolic process makes it a valuable compound for the development of drugs and therapies targeting leucine metabolism-related conditions.
Used in Food Industry:
Sodium ketoisocaproate is found in various food items, such as fruits, vegetables, and dairy products. Its presence in these food sources contributes to their nutritional value and may play a role in the overall health benefits associated with their consumption.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 4502-00-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,5,0 and 2 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 4502-00:
(6*4)+(5*5)+(4*0)+(3*2)+(2*0)+(1*0)=55
55 % 10 = 5
So 4502-00-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O3.Na/c1-4(2)3-5(7)6(8)9;/h4H,3H2,1-2H3,(H,8,9);/q;+1/p-1
4502-00-5Relevant articles and documents
Independent valine and leucine isotope labeling in Escherichia coli protein overexpression systems
Lichtenecker, Roman J.,Weinhaeupl, Katharina,Reuther, Lukas,Schoerghuber, Julia,Schmid, Walther,Konrat, Robert
, p. 205 - 209 (2013)
The addition of labeled α-ketoisovalerate to the growth medium of a protein-expressing host organism has evolved into a versatile tool to achieve concomitant incorporation of specific isotopes into valine- and leucine-residues. The resulting target proteins represent excellent probes for protein NMR analysis. However, as the side-chain resonances of these residues emerge in a narrow spectral range, signal overlap represents a severe limitation in the case of high-molecular-weight NMR probes. We present a protocol to eliminate leucine labeling by supplying the medium with unlabeled α-ketoisocaproate. The resulting spectra of a model protein exclusively feature valine signals of increased intensity, confirming the method to be a first example of independent valine and leucine labeling employing α-ketoacid precursor compounds.
Amino acid derivatives inhibiting extracellular matrix metalloproteinase and TNF alpha release
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Page column 36, (2010/11/29)
The invention concerns compounds of general formula (X) in which Y represents in particular —CONHOH, R1represents in particular a C1-C5alkyl group, AA represents an amino acid, or an amino acid sequence, and R3represents in particular a group of formula —NH—(CH2)2—SCH3. The invention also concerns the pharmaceutical compositions containing them, and the methods for obtaining them.
Dioxolanones as Synthetic Intermediates. Part 1. Synthesis of α-Keto Acids, α-Keto Aldehydes, and α-Ketols
Ramage, Robert,Griffiths, Gareth J.,Shutt, Fiona E.,Sweeney, John N. A.
, p. 1531 - 1537 (2007/10/02)
2,2-Pentamethylene-1,3-dioxolan-4-one (10) has been elaborated to provide 5'-ylidene derivatives using a Wittig approach.This apparently novel class of compounds is subject to nucleophilic attack at the 4-position because of strain inherent in the 5-membered ring.Thus alkaline hydrolysis leads to the formation of α-keto acids; hydride reduction of dioxolanones incorporating conjugated aryl substituents using di-isobutylaluminium hydride leads to α-keto-aldehydes; the reaction of dioxolanone (15) with methylmagnesium iodide gave the α-ketol (40).