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N-Oxalylglycine

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N-Oxalylglycine
Partially condensed, skeletal formula of N-oxalylglycine
Partially condensed, skeletal formula of N-oxalylglycine
Names
IUPAC name N-Oxaloglycine
Systematic IUPAC name (oxo)acetic acid
Identifiers
CAS Number
3D model (JSmol)
Abbreviations NOG
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.213.188 Edit this at Wikidata
MeSH oxalylglycine
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H5NO5/c6-2(7)1-5-3(8)4(9)10/h1H2,(H,5,8)(H,6,7)(H,9,10)Key: BIMZLRFONYSTPT-UHFFFAOYSA-N
SMILES
  • OC(=O)CNC(=O)C(O)=O
Properties
Chemical formula C4H5NO5
Molar mass 147.086 g·mol
Appearance Colorless solid
log P 1.232
Acidity (pKa) 2.827
Basicity (pKb) 11.170
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

N-Oxalylglycine is the organic compound with the formula HO2CC(O)NHCH2CO2H. This colourless solid is used as an inhibitor of α-ketoglutarate-dependent enzymes. It is isosteric with α-Ketoglutaric acid. Such enzymes are pervasive and, for example, are required for the synthesis of 4-hydroxyproline.

References

  1. Hausinger, R. P."Fe(II)/α-ketoglutarate-dependent hydroxylases and related enzymes" Critical Reviews of Biochemical Molecular Biology 2004, 39: pp 21-68. doi:10.1080/10409230490440541
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