ISSN:
0268-2605
Keywords:
Arsenic-containing lipids
;
2-trimethylarsonioethylphosphonic acid bromide
;
1,2-bis(palmitoyloxy)-3-propyl 2-trimethylarsonioethylphosphonate
;
arsenic-containing phosphonolipid
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 1,2-bis(palmitoyloxy)-3-propyl 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 16% 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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/aoc.590040204
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