Lanosterol
From Wikipedia, the free encyclopedia
| Lanosterol | |
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| IUPAC name | lanosta-8,24-dien-3-ol |
| Identifiers | |
| CAS number | [79-63-0] |
| MeSH | |
| SMILES | C[C@H](CCC=C(C)C)[C@H]1CC [C@]2(C)C1CCC3=C2CC[C@H] 4C(C)(C)[C@@H](O)CC[C@]34C |
| Properties | |
| Molecular formula | C30H50O |
| Molar mass | 426.70 g/mol |
| Melting point |
138-140 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived.
Contents |
[edit] 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.
[edit] 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) |
[edit] See also
[edit] 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:.
- 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:.
- 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:.
[edit] External links
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