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O9390

Sigma-Aldrich

N-Oxalylglycine

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C4H5NO5
CAS Number:
5262-39-5
Molecular Weight:
147.09
MDL number:
MFCD00913253
UNSPSC Code:
12352209
PubChem Substance ID:
329818940
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

solubility

deionized water: >10 mg/mL

storage temp.

2-8°C

SMILES string

OC(=O)CNC(=O)C(O)=O

InChI

1S/C4H5NO5/c6-2(7)1-5-3(8)4(9)10/h1H2,(H,5,8)(H,6,7)(H,9,10)

InChI key

BIMZLRFONYSTPT-UHFFFAOYSA-N

Biochem/physiol Actions

N-Oxalylglycine is an inhibitor of α-ketoglutarate-dependent enzymes and mimics the initial steps but does not initiate the hydroxylation process. N-Oxalylglycine has been used to inhibit Jumonji C-domain-containing histone lysine demethylases.

Features and Benefits

This compound is a featured product for Gene Regulation and Neuroscience research. Discover more featured Gene Regulation and Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Glutamate/GABA Synthesis and Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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α-Ketoglutaric acid ≥98.5% (NaOH, titration)

Sigma-Aldrich

K1750

α-Ketoglutaric acid

α-Ketoglutaric acid sodium salt ≥98% (titration)

Sigma-Aldrich

K1875

α-Ketoglutaric acid sodium salt

Lisa P Elia et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 39(17), 3332-3344 (2019-01-31)
Deficient progranulin levels cause dose-dependent neurological syndromes: haploinsufficiency leads to frontotemporal lobar degeneration (FTLD) and nullizygosity produces adult-onset neuronal ceroid lipofuscinosis. Mechanisms controlling progranulin levels are largely unknown. To better understand progranulin regulation, we performed a genome-wide RNAi screen using
Gulzhan Raiymbek et al.
eLife, 9 (2020-03-21)
H3K9 methylation (H3K9me) specifies the establishment and maintenance of transcriptionally silent epigenetic states or heterochromatin. The enzymatic erasure of histone modifications is widely assumed to be the primary mechanism that reverses epigenetic silencing. Here, we reveal an inversion of this
Nathaniel W Mabe et al.
Cell reports, 33(5), 108341-108341 (2020-11-05)
Dysregulated gene expression is a common feature of cancer and may underlie some aspects of tumor progression, including tumor relapse. Here, we show that recurrent mammary tumors exhibit global changes in gene expression and histone modifications and acquire dependence on
Xiongwen Cao et al.
Cell reports, 30(12), 4152-4164 (2020-03-27)
Histone methyl groups can be removed by demethylases. Although LSD1 and JmjC domain-containing proteins have been identified as histone demethylases, enzymes for many histone methylation states or sites are still unknown. Here, we perform a screening of a cDNA library
Tim J Wigle et al.
Journal of biomolecular screening, 20(6), 810-820 (2015-03-11)
Demethylation of histones by lysine demethylases (KDMs) plays a critical role in controlling gene transcription. Aberrant demethylation may play a causal role in diseases such as cancer. Despite the biological significance of these enzymes, there are limited assay technologies for

Articles

Glutamate/GABA Synthesis and Metabolism

Glutamine is a common precursor for the biosynthesis of both glutamate and GABA. Glutamine can be transported in and out of neurons and astrocytes utilizing different glutamine carriers. The neurotransmitter glutamate can be synthesized from glutamine by the action of phosphate-activated glutaminase.

Histone Modification and Chromatin Remodeling | Epigenetics

Epigenetic modifications are thought to occur through two key interconnected processes—DNA methylation and the covalent modification of histones.

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