Farnesyl pyrophosphate

Farnesyl pyrophosphate (FPP), also known as Farnesyl diphosphate, is an important intermediate in the mevalonate pathway and the terpenoid and steroid biosynthesis pathway in animals, plants, and bacteria. It is a C15 polyisoprene unit that is used in the biosynthesis of important biomolecules such as cholesterol, vitamin K, vitamin E, and coenzyme Q10.

Structure and Properties

Farnesyl pyrophosphate is a farnesyl molecule with two phosphate groups attached at one end. It is a colorless, oily liquid at room temperature. The molecule is highly reactive due to the presence of the pyrophosphate group, which makes it a good leaving group in biosynthetic reactions.

Biosynthesis

Farnesyl pyrophosphate is synthesized from isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) through the action of the enzyme farnesyl diphosphate synthase. This reaction is a key step in the mevalonate pathway and is regulated by feedback inhibition by downstream products such as cholesterol and dolichols.

Biological Role

Farnesyl pyrophosphate is a precursor to many important biomolecules. It is converted to squalene by the enzyme squalene synthase, which is the first step in the biosynthesis of cholesterol. It is also used in the synthesis of the side chain of coenzyme Q10, and in the post-translational modification of proteins through a process known as prenylation.

Clinical Significance

Inhibition of farnesyl pyrophosphate synthase, the enzyme that synthesizes FPP, is a target for the treatment of diseases such as hypercholesterolemia and osteoporosis. Drugs such as statins and bisphosphonates work by inhibiting this enzyme.

See Also

• Mevalonate pathway
• Terpenoid
• Steroid
• Cholesterol
• Vitamin K
• Vitamin E
• Coenzyme Q10