N-Oxalylglycine

Cayman Chemical Item Number 13944

NOG (CAS 5262-39-5)

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Description

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

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).

7. missing reference text

Synonyms
  • NOG
Formal Name N-​(carboxycarbonyl)-​glycine
CAS Number 5262-39-5
Molecular Formula C4H5NO5
Formula Weight 147.1
Formulation A crystalline solid
Purity ≥98%
λmax 219 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OC(C(NCC(O)​=O)​=O)​=O
InCHI Code
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​1S/C4H5NO5/c6-2(7)​1-5-3(8)​4(9)​10/h1H2,(H,5,8)​(H,6,7)​(H,9,10)​
InCHI Key
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BIMZLRFONYSTPT-UHFFFAOYSA-N

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N-Oxalylglycine is available in the following screening library:

Size Price Quantity Subtotal
5 mg $20.00 $0.00
10 mg $35.00 $0.00
50 mg $110.00 $0.00
100 mg $176.00 $0.00
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Pricing updated 2015-05-25. Prices are subject to change without notice.

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