Oxamic acid is an organic compound with the formula NH2C(O)COOH. It is a white, water-soluble solid. It is the monoamide of oxalic acid.[3] Oxamic acid inhibits lactate dehydrogenase A.[4] The active site of lactate dehydrogenase (LDH) is closed off once oxamic acid attaches to the LDH-NADH complex, effectively inhibiting it.[5]
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 Ball and stick model of oxamic acid
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| Names | |
|---|---|
| Preferred IUPAC name
Oxamic acid[1] | |
| Other names
Amino(oxo)acetic acid[1]
2-Amino-2-oxoacetic acid 2-oxoglycine Aminooxoacetic acid Oxalamic acid Oxamidic acid 2-Amino-2-oxoethanoic acid | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.006.768 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| NH2C(O)COOH | |
| Molar mass | 89.050 g·mol−1 |
| Appearance | White solid |
| Melting point | 209 °C[2] |
| Soluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oxamic acid also has applications in polymer chemistry. It increases the water solubility of certain polymers, including polyester, epoxide, and acrylic upon binding with them.[6]
See also
edit- Oxamate, the conjugate base of oxamic acid
References
edit- ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 415. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- ^ Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. p. 3.430. ISBN 978-1-4398-5511-9.
- ^ "Oxamic acid". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Archived from the original on 2016-12-01. Retrieved 2016-12-14.
- ^ Miskimins WK, Ahn HJ, Kim JY, Ryu S, Jung YS, Choi JY (2014). "Synergistic anti-cancer effect of phenformin and oxamate". PLOS ONE. 9 (1): e85576. doi:10.1371/journal.pone.0085576. PMC 3897486. PMID 24465604.
- ^ Raczyńska, Ewa D.; Hallmann, Małgorzata; Duczmal, Kinga (March 2011). "Quantum-chemical studies of amide–iminol tautomerism for inhibitor of lactate dehydrogenase: Oxamic acid". Computational and Theoretical Chemistry. 964 (1–3): 310–317. doi:10.1016/j.comptc.2011.01.017. ISSN 2210-271X.
- ^ Zarzyka-Niemiec, Iwona (2008-10-05). "Hydroxyalkylation of oxamic acid with propylene carbonate: Synthesis, composition, and properties of products". Journal of Applied Polymer Science. 110 (1): 66–75. doi:10.1002/app.28609. ISSN 0021-8995.
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