Lanosterol

Lanosterol

[luh-nos-tuh-rawl, -rol]
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.

Biosynthesis

Description Illustration Enzyme
Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene squalene synthase
Squalene is oxidized to 2,3-oxidosqualene (squalene epoxide) squalene monooxygenase
2,3-oxidosqualene is converted to a protosterol cation and finally to lanosterol lanosterol synthase
(step 2) (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.
  • I. Abe, M. Rohmer, G. D. Prestwich (1993). "Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes". Chemical Reviews 93 (6): 2189–2206.
  • 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.

External links

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