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2,3-oxidosqualene Information

2,3-(S) Oxidosqualene is an intermediate in the synthesis of the membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed from squalene by squalene monooxygenase. 2,3 oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.[1]

2,3-(R) Oxidosqualene is an inhibitor of lanosterol synthase.

References

  1. ^ Abe I. (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Products Reports 24 (6): 1311–31. doi:10.1039/b616857b. PMID 18033581.
· · Cholesterol and steroid metabolic intermediates
Mevalonate pathway
to HMG-CoA Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA
Ketone bodies Acetone · Acetoacetic acid · beta-Hydroxybutyric acid
to DMAPP Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate
Geranyl- Geranyl pyrophosphate · Geranylgeranyl pyrophosphate
Carotenoid Prephytoene diphosphate · Phytoene
Non-mevalonate pathway
DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP
To Cholesterol

Farnesyl pyrophosphate · Squalene · 2,3-Oxidosqualene · Lanosterol

Lanosterol · Lathosterol · 7-Dehydrocholesterol · Cholesterol

Lanosterol · Zymosterol · 7-Dehydrodesmosterol · Desmosterol · Cholesterol
Steroid
Corticosteroids (C21 pregnane)
Mineralocorticoids Pregnenolone · Progesterone · Cortodoxone · Corticosterone · Aldosterone
Glucocorticoids

Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · Cortisol

Cortisol · Cortisone
Sex steroids
Androgens (C19 androstane)

DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone

DHEA sulfate · Epitestosterone
Estrogens (C18 estrane) Estrone · Estradiol · Estriol
Nonhuman
Phytosterols Stigmasterol · Brassicasterol
Ergosterols Ergosterol · Ergocalciferol

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Categories: Epoxides | Triterpenes |

 

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