(R)-2,3-Dihydroxy-isovalerate

(R)-2,3-Dihydroxy-isovalerate, also known as α,β-dihydroxyisovalerate, is an important intermediate in the biosynthesis of branched-chain amino acids, particularly valine, leucine, and isoleucine.[1] This organic compound plays a crucial role in several metabolic pathways, including the superpathway of leucine, valine, and isoleucine biosynthesis, as well as pantothenate and coenzyme A (CoA) biosynthesis. It is produced from 3-hydroxy-3-methyl-2-oxobutanoic acid by the enzyme ketol-acid reductoisomerase (EC 1.1.1.86) and is subsequently converted to 2-oxoisovalerate by the enzyme dihydroxy-acid dehydratase (EC 4.2.1.9).[1]

(R)-2,3-Dihydroxy-isovalerate
Names
IUPAC name
(2R)-2,3-dihydroxy-3-methylbutanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C5H10O4/c1-5(2,9)3(6)4(7)8/h3,6,9H,1-2H3,(H,7,8)/t3-/m0/s1
    Key: JTEYKUFKXGDTEU-VKHMYHEASA-N
  • CC(C)([C@H](C(=O)O)O)O
Properties
C5H10O4
Molar mass 134.131 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

References

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  1. ^ a b "(R)-2,3-Dihydroxy-isovalerate". Human Metabolome Database (HMDB).