:Oxamic acid
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| ImageFile = oxamic_acid.svg
| ImageFile1 = Ball And Stick Model Of Oxamic Acid.png
| ImageCaption1 = Ball and stick model of oxamic acid
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| PIN = Oxamic acid{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 415 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}
| OtherNames = Amino(oxo)acetic acid
2-Amino-2-oxoacetic acid
2-oxoglycine
Aminooxoacetic acid
Oxalamic acid
Oxamidic acid
2-Amino-2-oxoethanoic acid
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| Section1 = {{Chembox Identifiers
| CASNo = 471-47-6
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| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QU60N5OPLG
| PubChem = 974
| ChemSpiderID = 949
| SMILES = C(=O)(C(=O)O)N
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| Section2 = {{Chembox Properties
| Formula = {{chem2|NH2C(O)COOH}}
| C=2|H=3|N=1|O=3
| Appearance = White solid
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| Solubility = Soluble
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| Section3 = {{Chembox Hazards
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Oxamic acid is an organic compound with the formula {{chem2|NH2C(O)COOH}}. It is a white, water-soluble solid. It is the monoamide of oxalic acid.{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/oxamic_acid#section=Depositor-Supplied-Synonyms |title=Oxamic acid |work=PubChem |publisher=National Center for Biotechnology Information, U.S. National Library of Medicine |date= |access-date=2016-12-14 |archive-date=2016-12-01 |archive-url=https://web.archive.org/web/20161201014207/https://pubchem.ncbi.nlm.nih.gov/compound/oxamic_acid#section=Depositor-Supplied-Synonyms |url-status=live }} Oxamic acid inhibits lactate dehydrogenase A.{{cite journal | vauthors = Miskimins WK, Ahn HJ, Kim JY, Ryu S, Jung YS, Choi JY | title = Synergistic anti-cancer effect of phenformin and oxamate | journal = PLOS ONE | volume = 9 | issue = 1 | pages = e85576 | year = 2014 | pmid = 24465604 | pmc = 3897486 | doi = 10.1371/journal.pone.0085576 | doi-access = free | bibcode = 2014PLoSO...985576M }} The active site of lactate dehydrogenase (LDH) is closed off once oxamic acid attaches to the LDH-NADH complex, effectively inhibiting it.{{Cite journal|last1=Raczyńska|first1=Ewa D.|last2=Hallmann|first2=Małgorzata|last3=Duczmal|first3=Kinga|date=March 2011|title=Quantum-chemical studies of amide–iminol tautomerism for inhibitor of lactate dehydrogenase: Oxamic acid|journal=Computational and Theoretical Chemistry|volume=964|issue=1–3|pages=310–317|doi=10.1016/j.comptc.2011.01.017|issn=2210-271X}}
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.{{Cite journal|last=Zarzyka-Niemiec|first=Iwona|date=2008-10-05|title=Hydroxyalkylation of oxamic acid with propylene carbonate: Synthesis, composition, and properties of products|journal=Journal of Applied Polymer Science|volume=110|issue=1|pages=66–75|doi=10.1002/app.28609|issn=0021-8995}}
See also
- Oxamate, the conjugate base of oxamic acid