N-Oxalylglycine • NOG (CAS 5262-39-5) (Inchi key BIMZLRFONYSTPT-UHFFFAOYSA-N) || Cayman Chemical | Supplier
N-Oxalylglycine
Item № 13944
CAS № 5262-39-5
Purity ≥98%
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SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL $0.00
5 mg $20.00 $0.00
10 mg $35.00 $0.00
50 mg $110.00 $0.00
100 mg $176.00 $0.00

Pricing updated 2015-09-01. Prices are subject to change without notice.

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Description
Synonyms
  • NOG

The jumonji domain-containing protein 2 (JMJD2) subfamily of histone demethylases have been shown to catalyze demethylation of the methylated forms of histone 3 lysine 9 (H3K9) and H3K36 in vitro and in cells.1 Because histone demethylases are implicated in certain diseases, including cancer, selective inhibitors are candidate anticancer agents as well as potential tools for elucidating the biological functions of JMJDs.2 N-Oxalylglycine, the amide analog of α-ketoglutarate, is a cell permeable inhibitor of α-ketoglutarate-dependent enzymes, including JMJD2A, JMJD2C, and JMJD2E (IC50s = 250, 500, and 24 μM, respectively).3,4,5,6 It can also inhibit the prolyl hydroxylase domain-containing proteins PHD1 and PHD2 with IC50 values of 2.1 and 5.6 μM, respectively.4,5,7

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Technical Information
Formal Name N-​(carboxycarbonyl)-​glycine
CAS Number 5262-39-5
Synonyms
  • NOG
Molecular Formula C4H5NO5
Formula Weight 147.1
Purity ≥98%
Formulation A crystalline solid
λmax 219 nm
SMILES OC(C(NCC(O)​=O)​=O)​=O
InChI Code ​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

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability 2 years
Product Downloads & Resources
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Download Product Insert 102 Kb PDF

Download Safety Data Sheet (SDS) 27 Kb PDF

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Additional Information

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References & Background Reading
Product Description References

1. Krishnan, S., Horowitz, S., and Trievel, R. Structure and function of histone H3 lysine 9 methyltransferases and demethylases. ChemBioChem 12 254-63 (2011).

2. Tian, X., and Fang, J. Current perspectives on histone demethylases. Acta Biochim Biophys Sin 39(2) 81-88 (2007).

3. Hamada, S., Kim, T., Suzuki, T., et al. Synthesis and activity of N-oxalylglycine and its derivatives as Jumonji C-domain-containing histone lysine demethylase inhibitors. Bioorg Med Chem Lett 19 2852-2855 (2009).

4. Hamada, S., Suzuki, T., Mino, K., et al. Design, synthesis, enzyme-inhibitory activity, and effect on human cancer cells of a novel series of Jumonji domain-containing protein 2 histone demethylase inhibitors. J Med Chem 53 5629-5638 (2010).

5. Rose, N.R., Ng, S.S., Mecinovic, J., et al. Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases. J Med Chem 51 7053-7056 (2008).

6. Rose, N.R., Woon, E.C.Y., Kingham, G.L., et al. Selective inhibitors of the JMJD2 histone demethylases: Combined nondenaturing mass spectrometric screening and crystallographic approaches. J Med Chem 53 1810-1818 (2010).

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