Homoisocitric acid

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Homoisocitric acid
Names
Preferred IUPAC name
1-Hydroxybutane-1,2,4-tricarboxylic acid
Other names
3-Carboxy-2-hydroxyadipic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C7H10O7/c8-4(9)2-1-3(6(11)12)5(10)7(13)14/h3,5,10H,1-2H2,(H,8,9)(H,11,12)(H,13,14)
    Key: OEJZZCGRGVFWHK-UHFFFAOYSA-N
  • InChI=1/C7H10O7/c8-4(9)2-1-3(6(11)12)5(10)7(13)14/h3,5,10H,1-2H2,(H,8,9)(H,11,12)(H,13,14)
    Key: OEJZZCGRGVFWHK-UHFFFAOYAM
  • O=C(O)CCC(C(=O)O)C(O)C(=O)O
Properties
C7H10O7
Molar mass 206.150 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Homoisocitric acid, with the systematic name 1-hydroxy-1,2,4-butanetricarboxylic acid is a positional isomer of homocitric acid, which is 2-hydroxy-1,2,4-butanetricarboxylic acid.[1] The stereoisomer found in nature, the (1R,2S) form, is an intermediate in the α-aminoadipate pathway of lysine biosynthesis where it is produced by homocitrate synthase:[2]

2D representation of the chemical structure of Q306140.
α-Ketoglutaric acid
+ acetyl-CoA
 
 
H2O
 
Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left
H2O
 
 
2D representation of the chemical structure of Q27104167.
(-)-Homoisocitric acid
+ Coenzyme A
 

It is a substrate for homoaconitate hydratase.[3]

2D representation of the chemical structure of Q27104167.
(-)-Homoisocitric acid
 
 
H2O
Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right
 
H2O
 
2D representation of the chemical structure of Q15410992.
cis-Homoaconitic acid

The compound is also acted on by homoisocitrate dehydrogenase to give 2-oxoadipic acid:[4]

2D representation of the chemical structure of Q27104167.
(-)-Homoisocitric acid
+ NAD+
 
 
 
H+
Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right
 
H+
 
2D representation of the chemical structure of 2-Oxoadipic acid .
2-Oxoadipic acid
+ CO2 + NADH
 

Homoisocitrate is an anion, salt, or ester of homoisocitric acid.

References

[edit]
  1. ^ "Homoisocitric Acid". U.S. National Library of Medicine; National Center for Biotechnology Information.
  2. ^ Enzyme 2.3.3.14 at KEGG Pathway Database.
  3. ^ Enzyme 4.2.1.36 at KEGG Pathway Database.
  4. ^ Enzyme 1.1.1.87 at KEGG Pathway Database.