(''S'')-2,3-Oxidosqualene ((''S'')-2,3-epoxysqualene) is an intermediate in the synthesis of the

cell membrane The cell membrane (also known as the plasma membrane or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of a cell from the outside environment (the extr ...

sterol A sterol is any organic compound with a Skeletal formula, skeleton closely related to Cholestanol, cholestan-3-ol. The simplest sterol is gonan-3-ol, which has a formula of , and is derived from that of gonane by replacement of a hydrogen atom on ...

precursor Precursor or Precursors may refer to: *Precursor (religion), a forerunner, predecessor ** The Precursor, John the Baptist Science and technology * Precursor (bird), hypothesized genus of fossil birds that was composed of fossilized parts of unre ...

lanosterol Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast, plant steroids are produced via cycloartenol. In the eyes of vertebrates, lanosterol is a natural constituent, havin ...

and

cycloartenol Cycloartenol is an important triterpenoid often found in plants. It belongs to the sterol class of steroids. It is the starting point for the synthesis of almost all plant steroids, making them chemically distinct from the steroids of fungi and a ...

, as well as

saponin Saponins (Latin ''sapon'', 'soap' + ''-in'', 'one of') are bitter-tasting, usually toxic plant-derived secondary metabolites. They are organic chemicals that become foamy when agitated in water and have high molecular weight. They are present ...

s. It is formed when

squalene Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as '' Squalus'' is a genus of sharks). ...

oxidized Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

by the enzyme

squalene monooxygenase Squalene monooxygenase (also called squalene epoxidase) is a eukaryotic enzyme that uses NADPH and diatomic oxygen to oxidize squalene to 2,3-oxidosqualene (squalene epoxide). Squalene epoxidase catalyzes the first oxygenation step in sterol b ...

. 2,3-Oxidosqualene is the

substrate Substrate may refer to: Physical layers *Substrate (biology), the natural environment in which an organism lives, or the surface or medium on which an organism grows or is attached ** Substrate (aquatic environment), the earthy material that exi ...

of various

oxidosqualene cyclase Oxidosqualene cyclases (OSC) are enzymes involved in cyclization reactions of 2,3-oxidosqualene to form sterols or triterpenes. There are two major groups of sterol-producing OSC enzymes: * Cycloartenol synthase (CAS), found in all plants, which ...

s, including

lanosterol synthase Lanosterol synthase () is an oxidosqualene cyclase (OSC) enzyme that converts 2,3-Oxidosqualene, (''S'')-2,3-oxidosqualene to a protosterol cation and finally to lanosterol. Lanosterol is a key four-ringed intermediate in cholesterol biosynthes ...

, which produces

, a precursor to

cholesterol Cholesterol is the principal sterol of all higher animals, distributed in body Tissue (biology), tissues, especially the brain and spinal cord, and in Animal fat, animal fats and oils. Cholesterol is biosynthesis, biosynthesized by all anima ...

. The

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

(''R'')-2,3-oxidosqualene is an inhibitor of lanosterol synthase.

References

External links

Oxidosqualene cyclase, PDB December 2007 Molecule of the Month
{{DEFAULTSORT:Oxidosqualene, 2,3- Epoxides Triterpenes Polyenes