Stereospecific hydration of unsaturated fatty acids by bacteria

Abstract

Three new 10-hydroxy fatty acids, all optically active, have been prepared by the anaerobic microbiological hydration of acis-9 double bond. Substrates that formed these new hydroxy fatty acids are linoleic, linolenic, and ricinoleic acids. The hydroxyl group has the D configuration and the methyl esters are levorotatory. Infrared, mass spectral, specific rotation and ultraviolet data on these compounds were determined. There was no migration of the unreated double bonds at C₁₂ and C₁₅ in linoleic or linolenic acids. The presence of a double bond in the 10-hydroxy fatty acids significantly increased the optical rotation of the methyl esters. The hydratase enzyme showed unusual specificity among Δ⁹ unsaturated acids. While it hydrates methylene interrupted and hydroxy unsaturated acids, it failed to hydrate either 9-decenoic, 12,13-epoxy- or 12-keto-cis-9-octadecenoic acids or sterculic acid.