Mevalonic acid

Mevalonic acid
Mevalonic-acid-2D-skeletal.png
Mevalonic acid2.png
Mevalonic acid spacefill.png
Names
IUPAC name

(3R)-3,5-Dihydroxy-3-methylpentanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
Properties
C6H12O4
Molar mass 148.158 g·mol−1
Except where otherwise noted, data are 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 a contraction of dihydroxymethylvalerolactone. The carboxylate anion of mevalonic acid, which is the predominant form in biological environments, is known as mevalonate and is of major pharmaceutical importance. Drugs like 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.

Mevalonate pathway: The figure doesn’t show that the HMG-CoA synthase needs another Acetyl-CoA as Substrate. Moreover, the enzyme that synthesizes mevalonic acid (HMG-CoA reductase) consumes two equivalents of NADH and releases one reduced CoA-SH.

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.