Abstract
IN Nature of March 9, p. 287, we recorded synthetic methods1 which we had worked out for the preparation of dialkyl fluorophosphonates (I) in high yield. These esters are stable liquids of high toxicity, and have powerful miotic action. The physiological action was found to be enhanced when R was a secondary alkyl grouping (for example, ^sopropyl, sec. butyl or qcfohexyl). In 1942 we handed several of these compounds to Dr. M. Dixon for test with enzymes. He reported2 that esters of fluorophos-phonic acid inhibit the action of the enzyme choline-esterase, and he showed that dwsopropyl fluoro-phosphonate is active in extremely low concentrations (for example, of the order of 10"10 M). On the other hand, sodium fluoride and ammonium fluorophos-phonate require a concentration of 10˜2 M to give 50 per cent inhibition of choline esterase activity. No other enzyme was found, the action of which was inhibited by the alkyl fluorophosphonates.
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References
McCombie, H., and Saunders, B. C., Nature, 157, 287 (1946).
Dixon, M., and Mackworth, J. F., Mode of Action of Fluorophosphonate Esters. Report to Ministry of Supply, April 23, 1942.
McCombie, H., and Saunders, B. C., Report No. 6 on Fluorophosphonates to Ministry of Supply, Sept. 30, 1942.
Burg, by communication, Feb. 19, 1943; and March 15, 1943.
McCombie, H., and Saunders, B. C., Report No. 14 on Fluorophosphonates to Ministry of Supply, Sept. 30, 1943.
British Secret Patent. Ministry of Supply, McCombie, H., Saunders, B. C., Chapman, N. B., and Heap, R., April 17, 1944.
McCombie, H., and Saunders, B. C., Report No. 17 on Fluorophosphonates to Ministry of Supply, Dec. 31, 1943.
McCombie, H., and Saunders, B. C., Report No. 15 on Fluorophosphonates to Ministry of Supply, Dec. 9, 1943.
McCombie, H., and Saunders, B. C., Report No. 18 on Fluorophosphonates to Ministry of Supply, July 4, 1944.
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MCCOMBIE, H., SAUNDERS, B. Alkyl Fluorophosphonates. Nature 157, 776–777 (1946). https://doi.org/10.1038/157776a0
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DOI: https://doi.org/10.1038/157776a0
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