Isopropylmalic acid (isopropylmalate) is an intermediate in the biosynthesis of leucine,[1] synthesized from oxoisovalerate by 2-isopropylmalate synthase and converted into isopropyl-3-oxosuccinate by 3-isopropylmalate dehydrogenase. Two isomers are important, the 2- and 3-isopropyl derivatives, and these are interconverted by isopropylmalate dehydratase.

Isopropylmalic acid

2-Isopropylmalic acid

3-Isopropylmalic acid
Names
IUPAC names
3-Isopropylmalic acid
2-Hydroxy-3-isopropylsuccinic acid
Other names
Isopropylmalate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.159.209 Edit this at Wikidata
EC Number
  • (2): 630-924-5
UNII
  • (2): InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)
    Key: BITYXLXUCSKTJS-UHFFFAOYSA-N
  • (3): InChI=1/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)
    Key: RNQHMTFBUSSBJQ-UHFFFAOYAR
  • InChI=1S/C7H12O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-5,8H,1-2H3,(H,9,10)(H,11,12)
    Key: RNQHMTFBUSSBJQ-UHFFFAOYSA-N
  • (2): O=C(O)C(O)(CC(=O)O)C(C)C
  • (3): O=C(O)C(O)C(C(=O)O)C(C)C
Properties
C7H12O5
Molar mass 176.168 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

References

edit
  1. ^ Strassman, Murray; Ceci, Louis N. (1963). "Enzymatic Formation of α-Isopropylmalic Acid, an Intermediate in Leucine Biosynthesis". Journal of Biological Chemistry. 238 (7): 2445–2452. doi:10.1016/S0021-9258(19)67991-3. PMID 13978769.