Mevalonic acid

Template:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer

Mevalonic acid

Template:Chembox image sbs cell
Template:Longitem	Template:Unbulleted list
ChEBI	Template:Unbulleted list
ChemSpider	Template:Unbulleted list
DrugBank	Template:Unbulleted list
EC Number	Template:Unbulleted list
KEGG	Template:Unbulleted list
Template:Longitem	Template:Unbulleted list
RTECS number	Template:Unbulleted list
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass

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.

Chemistry

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. Mevalonolactone acts to correct statin linked myopathy and limb girdle muscular disease caused by HMG CoA reductase mutation.

Biology

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.

File:Mevalonate pathway.svg

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.

See also

• Fructilactobacillus fructivorans
• Sake