Synthesis of a smoothened cholesterol: 18,19-di-nor-cholesterol.

ABSTRACT: Herein, we report the first synthesis of a demethylated form of cholesterol (18,19-di-nor-cholesterol), in which the C18 and C19 methyl groups of the β-face were eliminated. Recent molecular simulations modeling 18,19-di-nor-cholesterol have suggested that cholesterol's opposing rough β-face and smooth α-face play necessary roles in cholesterol's membrane condensing abilities and, additionally, that specific facial preferences are displayed as cholesterol interacts with different neighboring lipids and transmembrane proteins. Inspired by these poorly characterized biochemical interactions, an extensive 18-step synthesis was completed as part of a collaborative effort, wherein synthesizing a "smoothened" cholesterol analogue would provide a direct way to experimentally measure the significa

SUBMITTER: Mydock-McGrane L 

PROVIDER: S-EPMC4076041 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature