title: Synthesis of cholesterol analogs having varying length alkyl side chains including cholesterol-23, 23, 24, 24, 25, 26, 26, 26, 27, 27, 27-d(11) as probes of cholesterol's functions and properties.
abstract: Cholesterol-23, 23, 24, 24, 25, 26, 26, 26, 27, 27, 27-d11 and nondeuterated long-chain analogs of cholesterol were prepared by alkylation of cyano-containing sterols with isopentyl-d11 4-methylbenzenesulfonate (1.0equiv.) or with isoalkyl bromides, followed by reductive decyanation with excess potassium metal and a crown ether in toluene. The products are potentially useful probes of the role of the side-chain of cholesterol in the sterol's interactions with membrane lipids and proteins.
authors.affiliation: Department of Chemistry and Biochemistry, Queens College of the City University of New York, Flushing, NY 11367-1597, USA.
authors.forename: Dong Jae
authors.initials: DJ
authors.lastname: Baek
authors.forename: Robert
authors.initials: R
authors.lastname: Bittman
mesh_terms: D000478:Alkylation; D060326:Chemistry Techniques, Synthetic; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*; D008563:Membrane Lipids / Q000378:metabolism; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013261:Sterols / Q000737:chemistry / Q000378:metabolism
chemical_list: D008563:Membrane Lipids; D015335:Molecular Probes; D013261:Sterols; D002784:Cholesterol
keywords: Cholesterol synthesis; Cyano-containing sterol intermediates; Decyanation; Deuterium labeling