DIETHER PHOSPHINATE LECITHIN - CHEMICAL SYNTHESIS AND EFFECTS ON PHOSPHOLIPASE C

1. 1. A diether phosphinate analog of lecithin, dl-2-hexadecoxy-3-octadecoxy-propyl [2′-(trimethylammonium)ethyl]phosphinate, was prepared by the following series of reactions (R C18H37OCH2CH(OC16H33)CH2-; R (CH3)2CH-; Ms CH3SO2-): RI → RP(O) (OR′)CH2CH:CH2 (I) → RP(O) (OR′)CH2CHO (II) → RP(O) (OR′)CH2CH2OH (III) → PR(O)(OR′)CH2CH2OMs (IV) → RP(O) OR′)CH2CH2N(CH3)2 (V) → RP(O) (OR′)CH2CH2N+(CH3)3I- (VI) → RP(O)(O-)CH2CH2N+(CH3)3 (VII) Overall yield of pure VII as the monohydrate from I was 31%. 2. 2. The phosphinate lecithin was a good inhibitor of Clostridium welchii phospholipase C, somewhat stronger than 2-hexadecoxy-3-octadecoxypropylphosphonylcholine but weaker than 3,4-dioctadecoxybutylphosphonylcholine. It appeared to act as a simple competitive inhibitor, as do these phosphonate analogs. © 1969.