First synthesis of natural phosphatidyl-β-d-glucoside

Herein, we report the chemical synthesis of naturally occurring mammalian phosphatidyl-β-d-glucoside (PtdGlc), in order to confirm the proposed structure and to clarify its stereochemistry. We designed a convergent synthetic strategy, suitable to prepare sensitive PtdGlc derivatives. As an initial demonstration of our strategy, we successfully prepared both PtdGlc diastereomers as well as its sensitive arachidonyl analogue. The presence of both diastereomers in the natural sample was confirmed.

Chemical syntheses of phosphatidylglucoside (PtdGlc) and its derivatives were achieved via an H-phosphonate intermediate. The proposed structure of natural PtdGlc was confirmed. The suggested presence of sn-2-epimer in natural sample was validated.