2,3-Oxidosqualene

2,3-Oxidosqualene
Names
IUPAC name
2,2-Dimethyl-3-[(3E,7E,11E,15E)- 3,7,12,16,20-pentamethylhenicosa- 3,7,11,15,19-pentaenyl]oxirane
Other names
Squalene oxide
2,3-Squalene oxide
Squalene epoxide
Identifiers
7200-26-2 N
ChEBI CHEBI:78662 N
ChemSpider 4517951 YesY
Jmol interactive 3D Image
Image
MeSH 2,3-oxidosqualene
PubChem 5366020
Properties
C30H50O
Molar mass 426.717 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

(S)-2,3-Oxidosqualene ((S)-2,3-epoxysqualene) is an intermediate in the synthesis of the cell membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed when squalene is oxidized by the enzyme squalene monooxygenase. 2,3-Oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.[1]

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

References

  1. Abe I. (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Products Reports 24 (6): 1311–31. doi:10.1039/b616857b. PMID 18033581.

External links

This article is issued from Wikipedia - version of the Tuesday, August 18, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.