J. Lipid Res. Acyl Labeled PIP's available August 1, 2008
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Journal of Lipid Research, Vol. 12, 277-285, May 1971
Copyright © 1971 by Lipid Research, Inc.

New synthetic phosphinate analogues of lecithin

Arthur F. Rosenthal and Serge V. Chodsky

Department of Laboratories, The Long Island Jewish Medical Center, New Hyde Park, New York 11040

The chemical syntheses of two new, completely nonhydrolyzable phosphinate analogues of lecithin are described. These have the structures ROCH2CH(OR)CH2CH2P(O)(O-)CH2CH2N+(CH3)3 and ROCH2CH(OR')CH2P(O)(O-)CH2CH2CH2N+(CH3)3, where R = C18H37 and R' = C16H33; each is thus isosteric with lecithin on either side of the phosphorus function. The infrared spectra of these compounds undergo unexpected changes under mild acid, base, or adsorptive treatment. These are discussed and compared with related lecithin analogues, including the simple phosphinate C18H37P(O)(O-)CH2CH2N+(CH3)3, whose synthesis is also reported.

Supplementary key words isosteric • nonhydrolyzable • ethers • infrared spectra

Submitted on August 18, 1970
Accepted on December 22, 1970


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