Synthesis of ent-25-hydroxycholesterol

Emily J Westover; Douglas F Covey

doi:10.1016/j.steroids.2006.01.007

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Journal article

Peer reviewed

Synthesis of ent-25-hydroxycholesterol

Emily J Westover and Douglas F Covey

Steroids, Vol.71(6), pp.484-488

06/2006

DOI: https://doi.org/10.1016/j.steroids.2006.01.007

PMID: 16519912

Abstract

Cholesterol - chemistry

Cholesterol - analogs & derivatives

Stereoisomerism

Molecular Conformation

Hydroxycholesterols - chemistry

Cholesterol - chemical synthesis

Molecular Structure

Binding Sites

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).

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Title: Synthesis of ent-25-hydroxycholesterol
Creators: Emily J Westover - Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 S. Euclid, St. Louis, MO 63110, USA
Douglas F Covey
Publication Details: Steroids, Vol.71(6), pp.484-488
Publisher: United States
Grant note: GM47969 / NIGMS NIH HHS T32 HL07275 / NHLBI NIH HHS
Identifiers: 9923987127001921
Academic Unit: Department of Biochemistry
Language: English
Resource Type: Journal article

Synthesis of ent-25-hydroxycholesterol

Abstract

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