New, partially hydrolyzable synthetic analogues of lecithin, phosphatidyl ethanolamine, and phosphatidic acid

Abstract

The synthesis of two new synthetic analogues of lecithin, two of phosphatidyl ethanolamine (``cephalin''), and one new phosphatidic acid analogue is described. They comprise one of each of the following types: the ``isosteric'' diether lecithin and cephalin analogues ROCH2CH(OR)CH2CH2P(O)(O-)OCH2CH2N+R′3 (R = C18H37; R′ = H or CH3); and the ``hydrocarbon'' analogues of phosphatidic acid, lecithin, and cephalin, C17H35CH2CH(C18H37)CH2P(O)(R) = (R′); [R = R′ = OH; R = O-, R′ = OCH2CH2N+(CH3)3; and R = O-, R′ = OCH2CH2N+H3]. Infrared spectra and other properties of these compounds are described.

Keywords

• synthetic analogues
• lecithin
• cephalin
• phosphatidyl ethanolamine
• phosphatidic acid
• nonhydrolyzable