title: Synthesis of ent-25-hydroxycholesterol.
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).
authors.affiliation: Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 S. Euclid, St. Louis, MO 63110, USA.
authors.forename: Emily J
authors.initials: EJ
authors.lastname: Westover
authors.forename: Douglas F
authors.initials: DF
authors.lastname: Covey
mesh_terms: D001665:Binding Sites; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006888:Hydroxycholesterols / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006888:Hydroxycholesterols; C007997:25-hydroxycholesterol; D002784:Cholesterol