Lanosterol

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Lanosterol
Lanosterol skeletal.svg
Lanosterol-3D-sticks.png
Identifiers
CAS number 79-63-0 YesY
PubChem 246983
ChemSpider 216175 N
UNII 1J05Z83K3M N
MeSH Lanosterol
ChEBI CHEBI:16521 N
ChEMBL CHEMBL225111 N
Jmol-3D images Image 1
Properties
Molecular formula C30H50O
Molar mass 426.71 g/mol
Melting point 138 to 140 °C (280 to 284 °F; 411 to 413 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Lanosterol is a tetracyclic triterpenoid, which is the compound from which all steroids are derived.

Role in creation of steroids[edit]

Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14-Demethylation of lanosterol by CYP51 eventually yields cholesterol.

Simplified version of the lanosterol synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP), and squalene shown. Some intermediates are omitted.

Biosynthesis[edit]

Description Illustration Enzyme
Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene Cholesterol-Synthesis-Reaction10.png squalene synthase
Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide) Cholesterol-Synthesis-Reaction11.png squalene monooxygenase
2,3-Oxidosqualene is converted to a protosterol cation and finally to lanosterol Cholesterol-Synthesis-Reaction12.png lanosterol synthase
(step 2) Cholesterol-Synthesis-Reaction13.png (step 2)

See also[edit]

References[edit]

External links[edit]