Mevalonic Acid


Also found in: Medical, Wikipedia.

mevalonic acid

[¦mev·ə¦lan·ik ′as·əd]
(organic chemistry)
HO2C5H9COOH A dihydroxy acid used in organic synthesis.

Mevalonic Acid

 

3,5-dihydroxy-3-methyl-valeric acid, an important intermediary product of metabolism. Colorless water-soluble crystals. Melting point, 27°C; readily undergoes dehydration to form the corresponding 8-lactone (mevalolactone):

Physiologically active mevalonic acid is a ( + )-isomer. Mavelonic acid was discovered and isolated by American microbiologists (C. Folkers and others) in 1956. It is widely distributed in plants and animals.

The biosynthesis of mevalonic acid takes place in the microsomes of cells, with participation of three acetyl radicals. The resulting product of condensation undergoes irreversible reduction to mevalonic acid, which means that the latter may be regarded as a specific biogenetic unit. In nature, mevalonic acid is the initial material for the creation of a broad class of natural compounds, the isoprenoids. Synthetic mevalonic acid with an isotopic tag is widely used in studying the biosynthesis of various isoprenoids in organisms, as well as in acellular systems.

REFERENCES

Comfort, J. “Biosintez terpenoidov.” Uspekhi khimii, 1969, vol. 38, no. 5. (Article translated from English.)
“Natural Substances Formed Biologically From Mevalonic Acid.” Biochemical Society Symposium, no. 29, Liverpool, April 1969. London-New York, 1970.

E. P. SEREBRIAKOV

References in periodicals archive ?
Our laboratory conditions were incapable of evaluating MVK enzyme activity, and mevalonic acid levels were not measured in the urine because the patient was in a non-attack period.
Urinary concentration of mevalonic acid may be increased during acute febrile flares and may thus sometimes be useful to the diagnosis [5,6].
The pleiotropic effects of statins are mainlyowed to the inhibition of metabolic pathway of mevalonic acid. Statins decrease the products of the mevalonate pathway, including geranylgeranylpyrophosphate, which is required for the activity of small G-proteins (3).
Correll, et al., "Identification of Farnesol as the Non-Sterol Derivative of Mevalonic Acid Required for the Accelerated Degradation of 3-hydroxy-3-Methylglutaryl-Coenzyme A Reductase," J.
(9-13) These red, orange, or yellow compounds are composed of short, carbon chain-connected 6-carbon rings that are hydrophobic (e.g., combinations of mevalonic acid and lycopene or related compounds).
Statins are widely-used cholesterol-lowering agents that inhibit the rate-limiting step of cholesterol synthesis (the conversion of HMG-COA to mevalonic acid).
All are derived from a parent compound called mevalonic acid. Limonene and lycopene are examples of isoprenoids that inhibit cancer.
The almost 800 known lichen secondary metabolites can be classified according to the classic biosynthetic pathways: the poliketidic path (monocyclic phenols, depsides, depsidones, depsones, dibenzofurans, xanthones, naphtaquinones anthraquinones, macrocyclic lactones, aliphatic acids, etc.), the mevalonic acid path (steroids, carotenoids, etc.) and the shikimic acid path (amino acid derivatives, cyclopeptides, etc.) (Huneck 1999).
HMG-CoA could first be converted into mevalonic acid by the action of HMG-CoA reductase (EC1.1.1.34) with NADPH as a coenzyme.
Other compounds may also be quite specific, including 3-hydroxyglutarate for glutaric aciduria type I, mevalonic acid for mevalonic aciduria, N-acetylaspartate for Canavan disease, 4-hydroxycyclohexylacetate for hawkinsinuria, and 2-ketoadipate and 2-hydroxyadipate for 2-amino/2-ketoadipate aciduria.
Facts and artifacts in mevalonic aciduria: development of a stable isotope dilution GCMS assay for mevalonic acid and its application to physiological fluids, tissue samples, prenatal diagnosis and carrier detection.