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Iminosuccinic acid

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Iminosuccinic acid
Iminoaspartic acid.svg
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
PubChem CID
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).

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

Contents

Biosynthesis

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

L-Asparaginsaure - L-Aspartic acid.svg
aspartic acid
 
O2
H2O2
Iminosuccinic acid
O2
H2O2
 
Iminoaspartic acid.svg
iminosuccinic acid

Subsequent conversions

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

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

  1. ↑ Nasu S, Wicks FD, Gholson RK (1982). "L-Aspartate oxidase, a newly discovered enzyme of Escherichia coli, is the B protein of quinolinate synthetase". J. Biol. Chem. 257 (2): 626–32. doi: 10.1016/S0021-9258(19)68239-6 . PMID   7033218.
  2. ↑ Ollagnier-de Choudens, S., Loiseau, L., Sanakis, Y., Barras, F. and Fontecave, M. (2005). "Quinolinate synthetase, an iron-sulfur enzyme in NAD biosynthesis" (PDF). FEBS Lett. 579 (17): 3737–3743. doi: 10.1016/j.febslet.2005.05.065 . PMID   15967443.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ↑ Rousset C, Fontecave M, Ollagnier de Choudens S (August 2008). "The [4Fe-4S] cluster of quinolinate synthase from Escherichia coli: investigation of cluster ligands". FEBS Letters. 582 (19): 2937–44. Bibcode:2008FEBSL.582.2937R. doi: 10.1016/j.febslet.2008.07.032 . PMID   18674537.
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