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349631

Sigma-Aldrich

Dimethyl 2-oxoglutarate

96%

Sinónimos:

Dimethyl α-ketoglutarate

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About This Item

Fórmula lineal:
CH3O2CCH2CH2COCO2CH3
Número de CAS:
13192-04-6
Peso molecular:
174.15
MDL number:
MFCD00048052
UNSPSC Code:
12352100
PubChem Substance ID:
24861693
NACRES:
NA.22

assay

96%

form

liquid

refractive index

n20/D 1.439 (lit.)

bp

90-95 °C/0.4 mmHg (lit.)

density

1.203 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C7H10O5/c1-11-6(9)4-3-5(8)7(10)12-2/h3-4H2,1-2H3

InChI key

TXIXSLPEABAEHP-UHFFFAOYSA-N

Categorías relacionadas

General description

Dimethyl 2-oxoglutarate is a key intermediate formed during the Krebs cycle and an important nitrogen transporter in the biological metabolic pathways. The electrochemical behavior of dimethyl-2-oxoglutarate has been investigated by cyclic voltammetry, square wave voltammetry and differential pulse voltammetry using a glassy carbon electrode.

Application

Dimethyl 2-oxoglutarate can undergo cylocondensation with dinucleophiles, such as 1,2-phenylenediamine, 2-aminophenol and 2-aminobenzenethiol to form novel heterocycles.
Dimethyl 2-oxoglutarate may be used to synthesize the conformationally constrained PNA (peptide nucleic acid) -monomer capable of binding thymine in a triplex motif. It may be used in the synthesis of 4-aryl kainic acid analogs, via highly stereoselective Michael addition reaction with nitrostyrene.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Afzal Shah et al.
Bioelectrochemistry (Amsterdam, Netherlands), 77(2), 145-150 (2009-09-22)
The electrochemical behaviour of dimethyl-2-oxoglutarate (MOG), a key intermediate in the Krebs cycle and an important nitrogen transporter in the metabolic pathways in biological processes, was investigated by cyclic voltammetry, square wave voltammetry and differential pulse voltammetry using a glassy
Anne Goldbech Olsen et al.
Nucleosides, nucleotides & nucleic acids, 22(5-8), 1331-1333 (2003-10-21)
To expand the triplex recognition repertoire of Nucleic Acids, novel nucleobases that recognize thymine in a T-A base pair are still required. A novel conformationally constrained PNA-monomer (II) capable of binding T in a triplex motif was designed and synthesized
Yuan Cao et al.
Theranostics, 7(12), 3021-3033 (2017-08-26)
Increased glutamine metabolism is a hallmark of cancer. Mitochondrial glutamic pyruvate transaminase (GPT2) catalyzes the reversible transamination between alanine and α-ketoglutarate (α-KG), also known as 2-oxoglutarate, to generate pyruvate and glutamate during cellular glutamine catabolism. However, the precise role of
An efficient synthesis of 4-aryl kainic acid analogs.
Maeda H, et al.
Tetrahedron, 55(4), 943-954 (1999)
Arun Kumar Selvam et al.
Antioxidants (Basel, Switzerland), 9(2) (2020-02-09)
Kynurenine aminotransferase 1 (KYAT1 or CCBL1) plays a major role in Se-methylselenocysteine (MSC) metabolism. It is a bi-functional enzyme that catalyzes transamination and beta-elimination activity with a single substrate. KYAT1 produces methylselenol (CH3SeH) via β-elimination activities with MSC as a
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