Synthesis and characterization of rac-1,2-bis(palmitoyloxy)-3-propyl (2-trimethylarsonioethyl)phosphonate, an arsenic-containing phosphonolipid
✍ Scribed by Thomas Junk; Giuseppe C Pappalardo; Kurt J Irgolic
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 494 KB
- Volume
- 4
- Category
- Article
- ISSN
- 0268-2605
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✦ Synopsis
Arsenic analogs of lecithins (i.e. with replacement of nitrogen by arsenic in the choline group) are probably trace constituents of phospholipids in many organisms. Attempts to synthesize 1,2bis(palmitoy1oxy)-3propyl 2-trimethylarsonioethyl phosphate (arsenolecithin) according to wellestablished procedures for the synthesis of the corresponding nitrogen compound failed. However, 1,2-bis(palmitoyloxy)-3-propyl 2-trimethylarsonioethylphosphonate, an arsenic-containing phosphonolipid, was obtained in 14% yield by reacting 1,2-bis(palmitoyloxy)-3-iodopropane with silver 2-trimethylarsonioethylphosphonate in isopropanol. The precursors to the arsenic-containing phosphonolipid were obtained by quaternization of trimethylarsine with diethyl 2-bromoethylphosphonate, hydrolysis of the resulting product with concentrated hydrochloric acid, and reaction of the phosphonic acid with silver oxide to give silver 2-trimethylarsonioethylphosphonate. Quaternization and hydrolysis proceeded almost quantitatively. The silver phosphonate was not isolated but was used in situ.