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
Statins, also known as HMG-CoA reductase inhibitors, are a class of lipid-lowering medications that reduce illness and mortality in those who are at high risk of cardiovascular disease. They are the most common cholesterol-lowering drugs.
Low- ...
(which lower levels of
cholesterol) stop the production of mevalonate by inhibiting
HMG-CoA reductase
HMG-CoA reductase (3-hydroxy-3-methyl-glutaryl-coenzyme A reductase, official symbol HMGCR) is the rate-controlling enzyme (NADH-dependent, ; NADPH-dependent, ) of the mevalonate pathway, the metabolic pathway that produces cholesterol and oth ...
.
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
Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor to ...
of its terminal
alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
and
carboxylic acid
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
functional groups.
Biology
Mevalonic acid is a precursor in the
biosynthetic pathway known as the
mevalonate pathway that produces
terpenes and
steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...
s. 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 (3''R'')-
enantiomer
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
is the only one that is biologically active.
References
{{Authority control
Beta hydroxy acids
Diols
