2,3-Dihydroxy-3-methylpentanoic acid

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2,3-Dihydroxy-3-methylpentanoic acid
2,3-Dihydroxy-3-methylpentanoic acid.svg
Names
Preferred IUPAC name
2,3-Dihydroxy-3-methylpentanoic acid
Identifiers
3D model (JSmol)
ChemSpider
  • 7  Yes check.svgY
KEGG
MeSH 2,3-dihydroxy-3-methylpentanoic+acid
PubChem CID
  • InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9) Yes check.svgY
    Key: PDGXJDXVGMHUIR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)
    Key: PDGXJDXVGMHUIR-UHFFFAOYAA
  • CCC(C)(C(C(=O)O)O)O
  • O=C(O)C(O)C(O)(C)CC
Properties
C6H12O4
Molar mass 148.16 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2,3-Dihydroxy-3-methylpentanoic acid is an intermediate in the metabolism of isoleucine.

Metabolism

2,3-Dihydroxy-3-methylpentanoate is synthesized by the action of acetolactate mutase with subsequent reduction from α-aceto-α-hydroxybutyrate through 3-hydroxy-2-keto-3-methylpentanoate: [1]

α-aceto-α-hydroxybutyrate → 3-hydroxy-2-keto-3-methylpentanoate
3-hydroxy-2-keto-3-methylpentanoate + NAD(P)H → 2,3-dihydroxy-3-methylpentanoate + NAD(P)+

It is then processed by the action of dihydroxyacid dehydratase, which results in 2-keto-3-methylvalerate and water: [1]

2,3-dihydroxy-3-methylpentanoate → 2-keto-3-methylvalerate + H2O

Transamination of 2-keto-3-methylvalerate yields isoleucine.

References

  1. 1 2 Voet, Donald; Voet, Judith G. (2011). Biochemistry (4. ed.). Hoboken, NJ: Wiley. pp. 1074–1075. ISBN   978-0-470-91745-9.
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