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Mevalonic acid

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(Redirected fromMevalonate)
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 mass148.158 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Mevalonic acid (MVA) is a keyorganic compound in biochemistry; the name is a contraction ofdihydroxymethylvalerolactone. Thecarboxylate anion of mevalonic acid, which is the predominant form in biological environments, is known asmevalonate and is of major pharmaceutical importance. Drugs likestatins (which lower levels ofcholesterol) stop the production of mevalonate by inhibitingHMG-CoA reductase.[1]

Chemistry

[edit]

Mevalonic acid is very soluble in water and polar organic solvents. It exists in equilibrium with itslactone form, calledmevalonolactone, that is formed by internalcondensation of its terminalalcohol andcarboxylic acidfunctional groups. Mevalonolactone acts to correct statin linked myopathy andlimb girdle muscular disease caused by HMG CoA reductase mutation.[2]

Biology

[edit]

Mevalonic acid is a precursor in thebiosynthetic pathway known as themevalonate pathway that producesterpenes andsteroids. Mevalonic acid is the primary precursor ofisopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. Mevalonic acid ischiral 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.
  2. ^Yogev Y, Shorer Z, Koifman A, Wormser O, Drabkin M, Halperin D, Dolgin V, Proskorovski-Ohayon R, Hadar N, Davidov G, Nudelman H, Zarivach R, Shelef I, Perez Y, Birk OS (February 2023)."Limb girdle muscular disease caused by HMGCR mutation and statin myopathy treatable with mevalonolactone".Proc Natl Acad Sci U S A.120 (7): e2217831120.doi:10.1073/pnas.2217831120.PMC 9963716.PMID 36745799.

See also

[edit]
Synthesis
Degradation
Peroxisomal
Phytol
Other
Mevalonate pathway
toHMG-CoA
Ketone bodies
toDMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
ToCholesterol
FromCholesterol
toSteroid hormones
Nonhuman
ToSitosterol
ToErgocalciferol
Authority control databases: NationalEdit this at Wikidata
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