Synthesis of ent-25-hydroxycholesterol

Steroids
E J Westover, Douglas F Covey

Abstract

25-Hydroxycholesterol (25-HC) appears to play a role in several important biological processes, including regulating cellular cholesterol levels and promoting apoptosis. However, in most cases the mechanisms by which 25-HC elicits its biological effects are not known. Insights into mechanisms of 25-HC action can be gained by studying the activity of its enantiomer (ent-25-HC). ent-25-HC is physically and chemically identical to 25-HC; however, 25-HC and ent-25-HC can be distinguished in chiral environments, like a protein binding site. In order to probe the mechanisms of 25-HC action, we have synthesized the enantiomer of 25-HC (ent-25-HC).

References

Aug 11, 1978·Science·A A KandutschH J Heiniger
Feb 29, 1984·Biochimica Et Biophysica Acta·R P Holmes, N L Yoss
Feb 28, 2003·Steroids·Emily J Westover, Douglas F Covey
Feb 11, 2005·The Journal of Membrane Biology·E J Westover, D F Covey
Sep 1, 2005·The Journal of Biological Chemistry·Yvonne LangeTheodore L Steck

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Citations

Nov 23, 2007·Natural Product Reports·James R Hanson
Jun 1, 2014·Neuropharmacology·Andrew J LinsenbardtSteven Mennerick
Nov 16, 2012·Natural Product Reports·Jorge A R SalvadorM Luisa Sá e Melo
Aug 2, 2019·Investigative Ophthalmology & Visual Science·Kathleen S MolnarUsha P Andley
Jun 20, 2020·Journal of Neuroinflammation·Man Ying WongWenjie Luo

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Apoptosis

Apoptosis is a specific process that leads to programmed cell death through the activation of an evolutionary conserved intracellular pathway leading to pathognomic cellular changes distinct from cellular necrosis