Mevalonic Acid

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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 ?
The hyperimmunoglobulin D syndrome gene has been mapped to the mevalonate kinase (MVK) gene found on the 12th chromosome (22).
Interestingly, the thyroid hormones increase the hepatic de novo cholesterol synthesis by inducing the HMG-CoA reductase that catalyzes conversion of HMG-CoA to mevalonate, the initiation reaction in the biosynthesis of cholesterol (Ness et al.
gamma-Tocotrienol protects against ovariectomy-induced bone loss via mevalonate pathway as HMGCoA reductase inhibitor.
In these studies ezetimibe decreased the low-density lipoprotein (LDL) levels, but unlike statins it also increased the mevalonate levels.
The geranylgeranyl diphosphate production in rice probable occur in the plastids by methylerythritol phosphate pathway, whereas sesquiterpenes and triterpenes are usually synthesized in the cytoplasm through the mevalonate pathway (VRANOVA et al.
Resulting from mutations in the MVK gene (and hence also called mevalonate kinase deficiency), HIDS primarily afflicts those with European ancestry, and about half of patients are of Dutch ancestry.
Kline, "Simvastatin inhibition of mevalonate pathway induces apoptosis in human breast cancer cells via activation of JNK/CHOP/DR5 signaling pathway," Cancer Letters, vol.
De Libero, "Human T cell receptor [gamma]-[delta] cells recognize endogenous mevalonate metabolites in tumor cells," Journal of Experimental Medicine, vol.
In mammalian cells, the limiting substrate for dolichol biosynthesis is geranyl-geraniol (GGOH) of mevalonate pathway.
The acceptor molecules for GTs in plants are their own metabolites and xenobiotics, mevalonate derivatives, polyketides, amino acid derivatives and certain other synthetic chemicals (Bowles and Lim, 2010).
Statin drugs lower cholesterol levels by blocking the mevalonate pathway, which is common to the synthesis not only of cholesterol but also ubiquinone (coenzyme Q10 or CoQ10), dolichols, selenoproteins, and several other biochemicals of extreme importance to cellular activity.