Mevalonic acid

Source: Wikipedia, the free encyclopedia.
Mevalonic acid
Names
Preferred IUPAC name
(3R)-3,5-Dihydroxy-3-methylpentanoic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1 ☒N
    Key: KJTLQQUUPVSXIM-ZCFIWIBFSA-N ☒N
  • InChI=1/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
    Key: KJTLQQUUPVSXIM-ZCFIWIBFBE
  • C[C@@](O)(CCO)CC(=O)O
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).
☒N verify (what is checkY☒N ?)

Mevalonic acid (MVA) is a key

statins (which lower levels of cholesterol) stop the production of mevalonate by inhibiting HMG-CoA reductase.[1]

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 co-A reductase mutation.[2]

Biology

Mevalonic acid is a precursor in the

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

  1. PMID 1464741
    .
  2. PMID 36745799
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Mevalonic_acid&oldid=1193785304"