Mevalonic acid

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Mevalonic acid
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Names
IUPAC name
(3R)-3,5-Dihydroxy-3-methylpentanoic acid
Identifiers
150-97-0
ChEBI CHEBI:17710
ChemSpider 388367
Jmol-3D images Image
KEGG C00418
PubChem 439230
Properties
C6H12O4
Molar mass 148.16 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Mevalonic acid (MVA) is a key organic compound in biochemistry. The name is derived from a contraction of dihydroxymethylvalerolactone. The anion of mevalonic acid, which is the predominant form in biological environments is known as mevalonate, and is of major pharmaceutical importance. Drugs such as the statins (which lower levels of cholesterol) stop the production of mevalonate by inhibiting HMG-CoA reductase.[1]

Chemistry[edit]

Mevalonic acid is very soluble in water and polar organic solvents. It exists in equilibrium with its lactone form, called mevalonolactone, that is formed by internal condensation of its terminal alcohol and carboxylic acid functional groups.

Biology[edit]

Mevalonic acid is a precursor in the biosynthetic pathway known as the mevalonate pathway that produces terpenes and steroids. Mevalonic acid is the primary precursor of isopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. Mevalonic acid is chiral and the (3R)-enantiomer is the only one that is biologically active.

References[edit]

  1. ^ Endo, A. (1992). "The discovery and development of HMG-CoA reductase inhibitors". Journal of Lipid Research 33 (11): 1569–1582. PMID 1464741.