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'''(''S'')-2,3-Oxidosqualene''' ('''(''S'')-2,3-epoxysqualene''') is an intermediate in the synthesis of the ] ] precursors ] and ], as well as ]s. It is formed when ] is ] by the enzyme ]. 2,3-Oxidosqualene is the ] of various ]s, including ], which produces ], a precursor to ].<ref name="Abe">{{cite journal|author=Abe I.|year= 2007|title=Enzymatic synthesis of cyclic triterpenes|journal=Natural Product Reports|volume=24|pages=1311–31|pmid=18033581| doi = 10.1039/b616857b|issue=6}}</ref> '''(''S'')-2,3-Oxidosqualene''' ('''(''S'')-2,3-epoxysqualene''') is an intermediate in the synthesis of the ] ] ]s ] and ], as well as ]s. It is formed when ] is ] by the enzyme ]. 2,3-Oxidosqualene is the ] of various ]s, including ], which produces ], a precursor to ].<ref name="Abe">{{cite journal|author=Abe I.|year= 2007|title=Enzymatic synthesis of cyclic triterpenes|journal=Natural Product Reports|volume=24|pages=1311–31|pmid=18033581| doi = 10.1039/b616857b|issue=6}}</ref>


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

Revision as of 16:48, 14 October 2023

2,3-Oxidosqualene
Names
Preferred IUPAC name 2,2-Dimethyl-3-oxirane
Other names Squalene oxide
2,3-Squalene oxide
Squalene epoxide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
MeSH 2,3-oxidosqualene
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+Key: QYIMSPSDBYKPPY-BANQPHDMSA-N
  • InChI=1/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+Key: QYIMSPSDBYKPPY-BANQPHDMBU
SMILES
  • O1C(C)(C)C1CC/C(=C/CC/C(=C/CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C)C
  • CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/C)C
Properties
Chemical formula C30H50O
Molar mass 426.717 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

(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.

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

References

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

External links

Cholesterol and steroid metabolic intermediates
Mevalonate pathway
to HMG-CoA
Ketone bodies
to DMAPP
Geranyl-
Carotenoid
Non-mevalonate pathway
To Cholesterol
From Cholesterol
to Steroid hormones
Nonhuman
To Sitosterol
To Ergocalciferol
Categories:
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