Iminosuccinic acid

Chemical compound From Wikipedia, the free encyclopedia

Iminoaspartic acid (also known as iminosuccinate or iminoaspartate) is a dicarboxylic acid used in the biosynthesis of nicotinic acid and nicotinamide adenine dinucleotide.

Quick facts Names, Identifiers ...
Iminosuccinic acid
Names
IUPAC name
2-Iminobutanedioic acid
Other names
Iminoaspartic acid; 2-iminobutanedioic acid, iminosuccinate, alpha-iminosuccinate, iminosuccinic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)
    Key: NMUOATVLLQEYHI-UHFFFAOYSA-N
  • InChI=1/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)
    Key: NMUOATVLLQEYHI-UHFFFAOYAF
  • C(C(=N)C(=O)O)C(=O)O
Properties
C4H5NO4
Molar mass 131.087 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Close

Biosynthesis

The enzyme L-aspartate oxidase oxidises L-aspartic acid:[1]

2D representation of the chemical structure of aspartic acid .
aspartic acid
 
O2
H2O2
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
O2
H2O2
 
2D representation of the chemical structure of iminosuccinic acid .
iminosuccinic acid

Subsequent conversions

In Escherichia coli another enzyme, quinolinate synthase, takes iminosuccinic acid with dihydroxyacetone phosphate to form quinolinic acid.[2]

2D representation of the chemical structure of dihydroxyacetone phosphate .
dihydroxyacetone phosphate
+
 
2D representation of the chemical structure of iminosuccinic acid .
iminosuccinic acid
 
 
2 H2O
Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right
 
2 H2O
 
2D representation of the chemical structure of quinolinic acid .
quinolinic acid
+ H3PO4
 

This iron-sulfur protein requires a [4Fe-4S] cluster for activity. The quinolinic acid can be converted to nicotinic acid or incorporated into nicotinamide adenine dinucleotide.[3]

References

Related Articles

Wikiwand AI