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Journal of Lipid Research, Vol. 5, 121-125, January 1964
Copyright © 1964 by Lipid Research, Inc.

Relation of sterol structure to utilization in pleuropneumonia-like organisms

Paul F. Smith

Department of Microbiology, School of Medicine, University of South Dakota, Vermillion, South Dakota

Six sterols, ⁵-cholesten-3ßbeta;-ol (cholesterol), ⁵-cholesten-3-ol, cholestan-3ßbeta;-ol, cholestan-3-ol, coprostan-3ßbeta;-ol, and coprostan-3-ol, selected to represent variations in the configuration of the A and B rings and of the 3-hydroxyl group, were tested for physiological activity. Only ⁵-cholseten-3ßbeta;-ol and cholestan-3ßbeta;-ol supported growth of the pleuropneumonia-like organisms investigated, indicating the absolute requirement for a planar molecule with an equatorial 3-hydroxyl group. All six sterols were incorporated. The acetate esters of ⁵-cholestenols were less readily hydrolyzed than those of cholestanols, indicating that unsaturation in the B ring impedes the esterase. With a cis-fused A/B ring, esters of the axial 3-hydroxyl radical are more easily hydrolyzed than those of the equatorial 3-hydroxyl, while in the cholestanols (A/B trans) there is no such difference between epimers. The differences in effects of varying configurations of the sterol molecule are explained on the basis of steric hindrance of movement in the cell membrane.

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