Lanosterol

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Template:Chembox E number
Lanosterol
IUPAC name lanosta-8,24-dien-3-ol
Identifiers
3D model (JSmol)
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MeSH Lanosterol
Properties
C30H50O
Molar mass 426.70 g/mol
Melting point
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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

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) 400px squalene monooxygenase
2,3-oxidosqualene is converted to a protosterol cation and finally to lanosterol 400px lanosterol synthase
(step 2) 400px (step 2)

See also

References

  • E. J. Corey, W. E. Russey, P. R. Ortiz de Montellano (1966). "2,3-Oxidosqualene, an Intermediate in the Biological Synthesis of Sterols from Squalene". Journal of the American Chemical Society. 88 (20): 4750–4751. doi:10.1021/ja00972a056.
  • I. Abe, M. Rohmer, G. D. Prestwich (1993). "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes". Chemical Reviews. 93 (6): 2189–2206. doi:10.1021/cr00022a009.
  • A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni (1955). "Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen". Helvetica Chimica Acta. 38 (7): 1890–1904. doi:10.1002/hlca.19550380728.

External links



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