N-Oxalylglycine

N-Oxalylglycine

Names
IUPAC name 2-(Carboxymethylamino)-2-oxoacetic acid
Other names [(Carboxymethyl)amino](oxo)acetic acid
Identifiers
CAS Number	5262-39-5
3D model (Jmol)	Interactive image Interactive image
Abbreviations	NOG
ChEBI	CHEBI:44482
ChEMBL	ChEMBL90852
ChemSpider	2338366
ECHA InfoCard	100.213.188
MeSH	oxalylglycine
PubChem	3080614
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 [o]:c(:[oH])C[nH]:c(:[o])-c(:[o]):[oH] OC(=O)CNC(=O)C(O)=O
Properties
Chemical formula	C4H5NO5
Molar mass	147.09 g·mol^−1
Appearance	Colorless solid
log P	1.232
Acidity (pKa)	2.827
Basicity (pKb)	11.170
Related compounds
Related compounds	N-Acetylglycinamide Glycylglycine Oxalyldiaminopropionic acid
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

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.

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