The reaction of phosphoglycolipids and other lipids with hydrofluoric acid

1. The use of HF as a dephosphorylating reagent for phospholipids was examined. 2. Hydrolysis of phosphatidylethanolamine at 0 degrees C for 24h with 60% HF gives a good yield of diglyceride. Under similar conditions phosphatidyldiglucosyl diglyceride gives diglyceride and diglucosyl diglyceride. 3. The glycolipid is also obtained from hydrolysis of glycerylphosphoryldiglucosyl diglyceride. No lyso derivative of the glycolipid could be detected and the glycosidic linkage was also stable. 4. Triglycerides, unsaturated and cyclopropane fatty acids were unaffected by the reagent. 5. 1,2-Diglycerides and 1,3-diglycerides were partially isomerized and also gave small amounts of free fatty acid and monoglyceride. 6. Monoglycerides underwent extensive rearrangement to form 1,2- and 1,3-diglycerides. 7. Lysophosphatidylethanolamine also gave 1,2- and 1,3-diglycerides as well as monoglycerides. 8. The application of this procedure to the structure determination of various phosphoglycolipids is discussed.