Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.

Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.

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-me...

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Main Authors: H Pajouhesh, A J Hancock
Format: Article
Language:English
Published: Elsevier 1984-03-01
Series:Journal of Lipid Research
Online Access:http://www.sciencedirect.com/science/article/pii/S0022227520378287
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spelling doaj-d6001880a2154ef78fdfb20a93d745dd2021-04-25T04:16:47ZengElsevierJournal of Lipid Research0022-22751984-03-01253310312Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.H PajouheshA J HancockMonomethylamine 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.http://www.sciencedirect.com/science/article/pii/S0022227520378287
collection DOAJ
language English
format Article
sources DOAJ
author H Pajouhesh
A J Hancock
spellingShingle H Pajouhesh
A J Hancock
Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.
Journal of Lipid Research
author_facet H Pajouhesh
A J Hancock
author_sort H Pajouhesh
title Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.
title_short Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.
title_full Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.
title_fullStr Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.
title_full_unstemmed Synthesis of cyclopentano-N-methylphosphatidylethanolamines: aminolysis during the use of methylamine.
title_sort synthesis of cyclopentano-n-methylphosphatidylethanolamines: aminolysis during the use of methylamine.
publisher Elsevier
series Journal of Lipid Research
issn 0022-2275
publishDate 1984-03-01
description 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.
url http://www.sciencedirect.com/science/article/pii/S0022227520378287
work_keys_str_mv AT hpajouhesh synthesisofcyclopentanonmethylphosphatidylethanolaminesaminolysisduringtheuseofmethylamine
AT ajhancock synthesisofcyclopentanonmethylphosphatidylethanolaminesaminolysisduringtheuseofmethylamine
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