Journal of Lipid Research, Vol 25, 310-312, Copyright © 1984 by Lipid Research, Inc.
Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine
H Pajouhesh and AJ Hancock
Monomethylamine and N-benzyl-N-methylamine were used as nucleophiles in the
amination of the bromoethylester of cyclopentano-phosphatidic acid. The
former reagent led to extensive aminolysis and the quantitative formation
of N-methylpalmitamide, rather than the desired cyclopentano-
phosphatidyl-N-methylethanolamine. However, the method of Shapiro and
Rabinsohn (1964. Biochemistry. 3:603-605), in which N-benzyl-N- methylamine
was used as a nucleophile, was adapted for a successful synthesis.