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Lanosterol: Wikis

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Lanosterol
Lanosterol skeletal.svg
Lanosterol-3D-sticks.png
IUPAC name
Identifiers
CAS number 79-63-0 Yes check.svgY
PubChem 4861
MeSH Lanosterol
SMILES
Properties
Molecular formula C30H50O
Molar mass 426.71 g/mol
Exact mass 426.386166
Melting point

138-140 °C

 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

Contents

Role in creation of steroids

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

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

References

External links

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