MICROBIAL SULFOLIPIDS .3. DISULFATE OF (+)-1,14-DOCOSANEDIOL IN OCHROMONAS DANICA

A new sulfolipid, the disulfate of (+)-l,14-docosanediol, was isolated from the phytoflagellate, Ochromonas danica. It was characterized by synthesis of (DL)-l,14-docosanediol and its disulfate and by comparison of the synthetic materials with the natural materials. In order to determine the orientation of the natural secondary sulfate, it was necessary to explore the mechanism of solvolysis of sulfate esters in dioxane. It was found that solvolysis of secondary sulfates to alcohols in dioxane occurs with retention of configuration around the C-O bond of the alcohol. Comparison of the natural (+)-1,14-docosanediol rotation with the rotations of hydroxy acids of known absolute configuration suggest the natural sulfolipid is 1-(s)-14-docosanediol 1,14-disulfate. With one exception all other natural hydroxy fatty acids (where the hydroxyl is isolated and beyond the β position) have the R configuration. Chlorodocosanediols are obtained from the solvolyzed sulfatides. © 1969, American Chemical Society. All rights reserved.