Absolute configuration of dolichol

Abstract

A derivative of dolichol was formed and then chemically degraded to a small fragment containing the sole centre of asymmetry of the original molecule. Polarimetric comparison of this derivative with a standard prepared from (R)-citronellol showed dolichol to have an S-configuration at C-3. To determine the optical purity of dolichol a diastereoisomeric derivative was prepared and compared with standard diastereoisomers, which could be resolved by high-pressure liquid chromatography. Dolichols from pig liver, human liver and hen oviduct were analysed by this procedure and were all found to be greater than 95% S-configuration.