| Autor: |
Chandrakumar NS, Boyd VL, Hajdu J |
| Jazyk: |
angličtina |
| Zdroj: |
Biochimica et biophysica acta [Biochim Biophys Acta] 1982 May 13; Vol. 711 (2), pp. 357-60. |
| DOI: |
10.1016/0005-2760(82)90045-5 |
| Abstrakt: |
A facile and efficient synthesis of N-aceylaminoethylphosphorylcholines, a series of inhibitory substrate analogs of phospholipase A2, is described. The procedure consists of a three-step sequence including: (1) N-acylation of ethanolamine with fatty acid chloride, followed by (2) phosphorylation of the alcohol function using 2-chloro-2-oxo-1,3,2-dioxaphospholane and (3) nucleophilic ring opening of the cyclic phosphate triester (IV) with anhydrous trimethylamine. The resulting isosteric amide analogs of glycol-lecithins have been isolated in high yields. The synthesis is illustrated by the preparation of the compounds containing palmitoyl, stearoyl and lauroyl fatty acid side-chains. The N-acylaminoethylphosphorylcholines have been shown to function as reversible phospholipase A2 inhibitors. They are likely to become a new series of useful substrate analogs and an attractive replacement for the n-alkylphosphorylcholines commonly used as single-chain-carrying phospholipase inhibitors. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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