2,3-Dihydroxy-3-methylpentanoic acid

2,3-Dihydroxy-3-methylpentanoic acid
Names
	Preferred IUPAC name 2,3-Dihydroxy-3-methylpentanoic acid
Identifiers
CAS Number	562-43-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	7 ;
KEGG	C04104 ;
MeSH	2,3-dihydroxy-3-methylpentanoic+acid
PubChem CID	8;
CompTox Dashboard (EPA)	DTXSID00971589 ;
	InChI InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9) Key: PDGXJDXVGMHUIR-UHFFFAOYSA-N ; 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;
	SMILES CCC(C)(C(C(=O)O)O)O; O=C(O)C(O)C(O)(C)CC;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.

^ ^a ^b 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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