N-Oxalylglycine

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.[1] It is isosteric with α-Ketoglutaric acid. Such enzymes are pervasive and, for example, are required for the synthesis of 4-hydroxyproline.

N-Oxalylglycine
Partially condensed, skeletal formula of N-oxalylglycine
Names
IUPAC name
N-Oxaloglycine
Systematic IUPAC name
[(Carboxymethyl)amino](oxo)acetic acid
Identifiers
3D model (JSmol)
Abbreviations NOG
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.213.188
MeSH oxalylglycine
UNII
  • InChI=1S/C4H5NO5/c6-2(7)1-5-3(8)4(9)10/h1H2,(H,5,8)(H,6,7)(H,9,10) checkY
    Key: BIMZLRFONYSTPT-UHFFFAOYSA-N checkY
  • OC(=O)CNC(=O)C(O)=O
Properties
C4H5NO5
Molar mass 147.086 g·mol−1
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 [77 °F], 100 kPa).
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Infobox references

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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