title: Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol.
abstract: Using 3β-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis.
authors.affiliation: Department Chemie, Technische Universität Dresden, Germany.
authors.forename: Ratni
authors.initials: R
authors.lastname: Saini
authors.forename: Olga
authors.initials: O
authors.lastname: Kataeva
authors.forename: Arndt W
authors.initials: AW
authors.lastname: Schmidt
authors.forename: Yuqin
authors.initials: Y
authors.lastname: Wang
authors.forename: Anna
authors.initials: A
authors.lastname: Meljon
authors.forename: William J
authors.initials: WJ
authors.lastname: Griffiths
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Knölker
mesh_terms: D000818:Animals; D001921:Brain / Q000378:metabolism; D018360:Crystallography, X-Ray; D003897:Desmosterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D007536:Isomerism; D000071518:Liver X Receptors; D051379:Mice; D008968:Molecular Conformation; D057093:Orphan Nuclear Receptors / Q000737:chemistry / Q000378:metabolism
chemical_list: C587142:(24Z)-26-hydroxydesmosterol; D000071518:Liver X Receptors; D057093:Orphan Nuclear Receptors; D003897:Desmosterol
keywords: 26-Hydroxydesmosterol; Cholesterol; Desmosterol; Desmosterolosis; Steroids