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Monofluoro Aliphatic Compounds

  • Chapter
Pharmacology of fluorides

Abstract

In this chapter is given an account of the chemistry, biochemistry and pharmacology of monofluoro aliphatic organic compounds together with some account of their sources in Nature. Literature coverage extends to March, 19631. For a review of the earlier work on the physiology and pharmacology, see Chenoweth (1949). Other reviews have appeared (Saunders 1957; Peters 1957; and Pattison 1959). The numbering of the enzymes is from a recent report2.

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References

  • Aldous, J. G., and K. R. Rozee: The effect of pH on the toxicity of fluoroacetic acid. Biochem. J. 62, 605–610 (1956).

    PubMed  CAS  Google Scholar 

  • Aldous, J. G., and K. R. Rozee: The metabolic characteristics of yeast cells treated with fluoroacetic acid; evidence of the regulation of glucose oxidation by p11. J. cell. comp. Physiol. 52, 43–58 (1958).

    Article  CAS  Google Scholar 

  • Ali, D. A., A. G. Callely, and M. Hayes: Ability of a vibrio grown on a benzoate to oxidize p-fluorobenzoate. Nature (Loud.) 196, 194–195 (1962).

    Article  CAS  Google Scholar 

  • Annison, E. F., K. J. Hill, D. B. Lindsay, and R. A. Peters: Fluoroacetate poisoning in sheep. J. comp. Path. 70, 145–155 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Avi-Don, Y.: A study of the effect of particle-bound y-glutamyl transpeptidase on the product of interaction of fluoropyruvate with glutathione. Biochem. J. 76, 370–374 (1960).

    Google Scholar 

  • Avi-Don, Y., and J. Mager: The effect of fluoropyruvate on the respiration of animal-tissue preparations. Biochem J. 63, 613–618 (1956a).

    Google Scholar 

  • Avi-Don, Y., and J. Mager: A spectrophotometric method for determination of cysteine and related compounds. J. biol. Chem. 222, 249–258 (1956b).

    Google Scholar 

  • Bacq, Z. M., and P. A. Alexander: Fundamentals of radiobiology, 555pp., 2nd Ed. Oxford: — Pergamon Press 1961.

    Google Scholar 

  • S. Bliéecq-Hutter, and C. Liébecq: Protection against irradiation afforded by sodium fluoroacetate. Radiat. Res. 13, 286–297 (1960).

    Article  Google Scholar 

  • Badeniiuizen, N. P., and J. Slinger: Detection of monofluoroacetic acid in Gifblaar. (Dichapetalum cymosum (Hook) Engl) S Afr. J. Sci. 50, 269–270 (1954).

    Google Scholar 

  • Barbour, A. K., L. J. Belf, and M. W. Buxton: The preparation of organic fluorine compounds by halogen exchange. In: M. Stacey, J. C. Tatlow and A. G. Sharpe, Eds. Advances in Fluorine Chemistry, Vol. 3, 181–270. London: Butterworths 1963.

    Google Scholar 

  • Bartlett, G. R.: Mechanism of action of 2-fluoroethanol. J. Pharmacol. exp. Ther. 106, 464–467 (1952).

    PubMed  CAS  Google Scholar 

  • Bartlett, G. R., and E. S. G. Barron: The effect of fluoroacetate on enzymes and on tissue metabolism. Its use for the study of the oxidative pathway of pyruvate metabolism. J. biol. Chem. 170, 67–82 (1947).

    CAS  Google Scholar 

  • Beatty, C. H., and E. S. West: The effect of substances related to the tricarboxylic acid cycle upon ketosis. J. biol. Chem. 190, 603–610 (1951).

    PubMed  CAS  Google Scholar 

  • Benitez, O., G. R. Pscheidt, and W. E. Stone: Formation of ammonium ion in the cerebrum in fluoroacetate poisoning. Amer. J. Physiol. 176, 488–492 (1954).

    PubMed  CAS  Google Scholar 

  • Bergmann, E. D., and S. Cohen: Organic fluorine compounds. Part IX. The preparation of fluoroacetone and 1:3-difluoroacetone. J. chem. Soc. 1958, 2259–2262.

    Google Scholar 

  • Bergmann, E. D., and S. Cohen: Organic fluorine compounds. Fluorine derivatives of mevalolactone. Tetrahedron Letters, No. 8, 20–22 (1960).

    Article  Google Scholar 

  • Bergmann, E. D., and S. Cohen: Organic fluorine compounds. Part Xxii. Fluorine analogues of mevalonic acid. J. chem. Soc. 1961 a, 3457–3460.

    Google Scholar 

  • Bergmann, E. D., and S. Cohen: Organic fluorine compounds. Part Xxvi. Synthesis of a-fluoro-ß-alanine. J. chem. Soc. 1961 b, 4669–4671.

    Google Scholar 

  • Bergmann, E. D., S. Cohen, and I. Shahak: Organic fluorine compounds. Part Xii Preparation and reactions of diethyl fluoromalonate. J. chem. Soc. 1959, 3286–3289.

    Google Scholar 

  • Bergmann, E. D., S. Cohen, and I. Shahak: Organic fluorine compounds. Part XX. Some reactions of 1-chloro-3-fluoropropan2-ol and epifluorohydrin. J. chem. Soc. 1961, 3448–3452.

    Google Scholar 

  • Bergmann, E. D., and R. Ikan: The reaction of diazoketones with anhydrous hydrofluoric acid. Chem. and Ind. ( London ) 1957, 394.

    Google Scholar 

  • Bergmann, E. D., and I. Shahax: Transformation of toluene-p-sulphonates into fluorides. Chem. and Ind. ( London ) 1958, 157.

    Google Scholar 

  • Bergmann, E. D., and I. Shahax: Triethyl a-fluoroaconitate. Nature (Lond.) 185, 529–530 (1960).

    Article  CAS  Google Scholar 

  • Bergmann, E. D., and I. Shahax: A simple preparation of fluoromalonic acid esters. Chem. and Ind. ( London ) 1961, 591.

    Google Scholar 

  • Black, S., and J. O. Hutchens: The oxidation of acetate by yeast in the presence of fluoro-acetate. Arch. Biochem. 17, 211–223 (1948).

    PubMed  CAS  Google Scholar 

  • Blank, I., J. Mager, and E. D. Bergmann: Studies of organic fluorine compounds. Part IV. Synthesis of esters of fluoro-oxaloacetic and of fluoropyruvic acid. J. chem. Soc. 1955, 2190–2193.

    Google Scholar 

  • Blohm, T. R.: Fluoroacetylcholine bromide and some other choline ester salts. J. Amer. chem. Soc. 73, 5445–5446 (1951).

    Article  CAS  Google Scholar 

  • Blumgart, H. L., D. R. Gilligan, and J. H. Schwartz: The elimination of ethyl iodide after inhalation and its relation to therapeutic administration. J. clin. Invest. 9, 635–650 (1931).

    Article  PubMed  CAS  Google Scholar 

  • Bowers, A.: Steroids. Cxxix. A new general route to fluorinated steroids. J. Amer. chem. Soc. 81, 4107–4108 (1959).

    Article  CAS  Google Scholar 

  • Bowers, A., P. G. Holton, E. Denot, M. C. Loza, and R. UrqurzA: Steroids. Clxxxviii. New fluorination procedures. Part 3. cis-Addition of fluorine to a steroid olefin. A new route to 6 a-fluoro-z14–3-ketones. J. Amer. chem. Soc. 84, 1050–1053 (1962).

    Article  CAS  Google Scholar 

  • Bowers, A., L. C. Ibanez, E. Denot, and R. Becerra: Steroids. Cxxxix New fluorination procedures. Part I. The addition of Br—F and I—F to cyclohexene and a variety of unsaturated steroids. J. Amer. chem. Soc. 82, 4001–4007 (1960).

    Article  CAS  Google Scholar 

  • Brady, R. O.: Fluoroacetyl coenzyme A. J. biol. Chem. 217, 213–224 (1955).

    PubMed  CAS  Google Scholar 

  • Brady, R. O.: Enzymic synthesis of fatty acids by aldol condensation. Proc. Nat. Acad. Sci. (Wash.) 44, 993–998 (1958).

    Article  CAS  Google Scholar 

  • Bronnert, D. L. E., and B. C. Saunders: Toxic fluorine compounds containing the C—F link XI. Lability of the fluorine atom in 2-fluoroethanol. Tetrahedron 10, 160–163 (1960).

    Article  CAS  Google Scholar 

  • Brown, P. J., and B. C. Saunders: A new synthesis of monofluorocitric acid. Chem. and Ind. ( London ) 1962, 307–308.

    Google Scholar 

  • Buchanan, J. M., and C. B. Anfinsen: Partial purification of aconitase. J. biol. Chem. 180, 47–54 (1949).

    PubMed  CAS  Google Scholar 

  • Buchanan, R. L., F. H. Dean, and F. L. M. Pattison: y-Fluoroglutamic acid. Canad. J. Chem. 40, 1571–1575 (1962a).

    Article  CAS  Google Scholar 

  • Buchanan, R. L., F. H. Dean, and F. L. M. Pattison: The synthesis of a-monofluorocarboxylic acids. Preprints of the Second International Symposium on Fluorine Chemistry, Estes Park, Colorado, July, pp. 385–390 (1962 b).

    Google Scholar 

  • Buchanan, R. L., and F. L. M. Pattison: Unpublished results (1962).

    Google Scholar 

  • Buchanan, R. L., and F. L. M. Pattison: Unpublished results (1963).

    Google Scholar 

  • Buckle, F. J., F. L. M. Pattison, and B. C. Saunders: Toxic fluorine compounds containing the C—F link. Part VI. w-Fluorocarboxylic acids and derivatives. J. them. Soc. 1949, 1471–1479.

    Google Scholar 

  • Buffa, P., G. F. Azzone, E. Carafoli e U. Muscatello: Modificazione biochimiche mitocondriali e tessutali in relazione ad alcune ipo-ed i perterermie sperimentali del ratto. Sperimentale 110, 79–107 (1960a).

    CAS  Google Scholar 

  • Buffa, P., E. Carafoli, and U. Muscatello: Differenze metaboliche tre diaframma e muscolo grande dorsale del ratto rivelate dall intossicazione da fluoroacetato. Accad. Naz. dei Lincei. Xxviii Fase 6. Serie (iii) pp. 929–936 (1960 b).

    Google Scholar 

  • Buffa, P., and R. A. Peters: The in vivo formation of citrate induced by fluoroacetate and its significance. J. Physiol. (Lond.) 110, 488–500 (1949).

    CAS  Google Scholar 

  • Buffa, P., R. A. Peters, and R. W. Wakelin: Biochemistry of fluoroacetate poisoning Isolation of an active tricarboxylic acid fraction from poisoned kidney homogenates. Biochem. J. 48, 467–477 (1951).

    PubMed  CAS  Google Scholar 

  • Bulen, W. A., J. E. Varner, and R. C. Burrell: Separation of organic acids from plant tissues. Anal. Chem. 24, 187–190 (1952).

    Article  CAS  Google Scholar 

  • Bullwinkle, R., R. H. Fallon, T. C. Fleming, and A. B. Hastings: Note on the acid-base balance of the blood of rabbits following the intracerebral injection of fluorocitrate. Quart. J. exp. Physiol. 40, 269–271 (1955).

    PubMed  CAS  Google Scholar 

  • Busch, H., and V. R. Potter: Localisation of the enzymatic block in kidneys of rats treated with fluoroacetate. Proc. Soc. exp. Biol. (N. Y.) 81, 172–175 (1952).

    Article  CAS  Google Scholar 

  • Callely, A. G., and S. Dagley: A possible lethal synthesis of monofluoromalonate. Biochem. biophys. Acta (Amst) 35, 256–257 (1959).

    Article  CAS  Google Scholar 

  • Cater, D. B., and R. A. Peters: The occurrence of renal changes resembling nephrosis, in rats poisoned with fluorocitrate. Brit. J. exp. Path. 42, 278–289 (1961).

    PubMed  CAS  Google Scholar 

  • Chapman, N. B., and J. L. Levy: Nucleophilic displacement of fluorine from organic compounds. Part II. Kinetics of the reactions of alkyl fluorides with ethanolic sodium ethoxide. J. chem. Soc. 1952a, 1673–1677.

    Google Scholar 

  • Chapman, N. B., and J. L. Levy: Nucleophilic displacement of fluorine from organic compounds. Part Iii. Acid-catalysed solvolysis of alkyl fluorides in aqueous ethanol. J. chem. Soc. 1952 b, 1677–1682.

    Google Scholar 

  • Chari-Bitron, A.: A study on the toxicity and the biochemical effects of monofluoromalonate. Biochem. Pharmacol. 6, 169–176 (1961).

    Article  Google Scholar 

  • Chari-Bitron, A., and Y. Avi-DoR: Effect of fluoropyruvate on the swelling, phosphorylation and respiration of guinea pig liver mitochondria. Biochem. J. 71, 572–578 (1959).

    Google Scholar 

  • Chenoweth, M. B.: Monofluoroacetic acid and related compounds. Pharmacol. Rev. 1, 383–424 (1949).

    Google Scholar 

  • Chenoweth, M. B., and A. Gilman: Studies on the pharmacology of fluoroacetate. 1. Species response to fluoroacetate. J. Pharmacol. exp. Ther. 87, 90–103 (1946).

    PubMed  CAS  Google Scholar 

  • Chenoweth, M. B., A. Kandel, L. B. Johnson, and D. R. Bennett: Factors influencing fluoroacetate poisoning. Practical treatment with glycerol monoacetate. J. Pharmacol. exp. Ther. 102, 31–54 (1951).

    PubMed  CAS  Google Scholar 

  • Clarke, D. A., and W. F. Riker: The effect of fluoroacetate on the sartorius muscle of the frog. J. Pharmacol. exp. Ther. 99, 118–131 (1950).

    PubMed  CAS  Google Scholar 

  • Cole, B. T., F. L. Engel, and J. Fredericks: Sodium fluoroacetate diabetes: Correlations between glycemia, ketonemia and tissue citrate levels. Endocrinology 56, 675–683 (1955).

    Article  PubMed  CAS  Google Scholar 

  • Cole, B. T., F. L. Engel, and K. Hewson: Some metabolic effects of sodium fluoracetate poisoning in the rat. Fed. Proc. 13, 28 (1954).

    Google Scholar 

  • Conway, E. J., and E. O’Malley: The nature of the cation exchanges during yeast fermentation with formation of 0.02 N H ion. Biochem. J. 40, 59–67 (1946).

    CAS  Google Scholar 

  • Dagley, S., and J. R. L. Walker: Accumulation of citrate and pyruvate during growth of a vibrio in the presence of fluoroacetate. Biochem. biophys. Acta (Amst) 21, 441–447 (1956).

    Article  CAS  Google Scholar 

  • Dawson, R. M. C.: Cerebral amino acids in fluoroacetate poisoned, anaesthetised and hypoglycaemic rats. Biochim. biophys. Acta (Amst) 11, 548–552 (1953).

    Article  CAS  Google Scholar 

  • Dawson, R. M. C., and R. A. Peters: Observations upon the behaviour of some phosphate esters in brain at the start of convulsions induced by fluorocitrate and fluoroacetate. Biochim. biophys. Acta (Amst) 16, 254–257 (1955).

    Article  CAS  Google Scholar 

  • Dawson, R. M. C., and D. Richter: Effects of stimulation on the phosphate esters of the brain. Amer. J. Physiol. 160, 203–211 (1949).

    Google Scholar 

  • Dean, F. H., and F. L. M. Pattison: Unpublished results (1962).

    Google Scholar 

  • Dean, F. H., and F. L. M. Pattison: Monofluorosuccinic acid. Canad. J. Chem. 41, 1833–1836 (1963).

    Article  CAS  Google Scholar 

  • Dear, R. E. A., and F. L. M. Pattison: Toxic fluorine compounds. Xviii. The synthesis of the toxic principle of Dichapetalum toxicarium (18-fluoro-ci8–9-octadecenoic acid) and related w-fluoro unsaturated acids. J. Amer. chem. Soc. 85, 622–626 (1963).

    Article  CAS  Google Scholar 

  • Dickman, S. R., and A. A. Cloutier: Factors affecting the activity of aconitase. J. biol. Chem. 188, 379–388 (1951).

    PubMed  CAS  Google Scholar 

  • Dixon, G. H., H. L. Kornberg, and P. Lund: Purification and properties of malate synthetase. Biochim. biophys. Acta (Amst.) 41, 217–233 (1960).

    Article  CAS  Google Scholar 

  • Dixon, M.: Biochem. Soc. Symposia. No. 2. p. 42. On the Biochemical Reactions of Chemical Warfare Agents. Cambridge Univ. Press (1948).

    Google Scholar 

  • Dixon, M., and D. M. Needham: Biochemical research on chemical warfare agents. Nature (Lond.) 158, 432–438 (1946).

    Article  CAS  Google Scholar 

  • Dominguez, A. M., F. E. Shideman, H. R. Mahler, and H. Rift: Effects of monofluoroacetic, 4-fluorobutanoic and 6-fluorohexanoic acids on fatty acid and Krebs cycle oxidations. Fed. Proc. 13, 1149 (1954).

    Google Scholar 

  • Edgell, W. F., and L. Parts: Synthesis of alkyl and substituted alkyl fluorides from p-toluenesulfonic acid esters. The preparation of p-toluenesulfonic acid esters of lower alcohols. J. Amer. chem. Soc. 77, 4899–4902 (1955).

    Article  CAS  Google Scholar 

  • Elliott, W. B., and G. Kalnitsky: A mechanism for fluoroacetate inhibition. J. biol. Chem. 186, 487–493 (1950).

    PubMed  CAS  Google Scholar 

  • Elliott, W. B., and A. Marcus: Enzymatic reactions of fluoroacetyl phosphate. J. biol. Chem. 234, 1011–1014 (1959);

    PubMed  Google Scholar 

  • Elliott, W. B., and A. Marcus: Enzymatic reactions of fluoroacetyl phosphate. Fed. Proc. 14, 201 (1955).

    Google Scholar 

  • Elliott, W. B., and A. Marcus: Fluoroacetyl phosphate, preparation and properties. J. Amer. chem. Soc. 80, 4287 (1958).

    Article  Google Scholar 

  • Elliott, W. B., and A. H. Phillips: Effect of fluoroacetate on glucose metabolism in vivo. Archiv. Biochem. 49, 389–395 (1954).

    Article  CAS  Google Scholar 

  • Elsden, S. R., and J. G. Ormerod: The effect of monofluoroacetate on the metabolism of Rhodospirillum rubrum. Biochem. J. 63, 691–701 (1956).

    PubMed  CAS  Google Scholar 

  • Engel, F. L., K. Hewson, and F. T. Cole: Carbohydrate and ketone metabolism in the sodium fluoroacetate-poisoned rat. S.F.A. Diabetes. Amer. J. Physiol. 179, 325–332 (1954).

    CAS  Google Scholar 

  • Fairhurst, A. S., R. E. Smith, and E. M. Gal: The effects of fluoro-compounds on oxidative phosphorylation. Biochem. Pharmacol. 1, 273–279, 280–287 (1958).

    Google Scholar 

  • Fanshier, D. W., L. K. Gottwald, and E. KuN: Enzymic synthesis of monofluorocitrate from ß-fluoro-oxaloacetate. J. biol. Chem. 237, 3588–3596 (1962).

    CAS  Google Scholar 

  • Farah, A., G. Graham, and F. Koda: The action of sodium fluoroacetate on the renal tubular transport of para-aminohippurate and glucose in the dog. J. Pharmacol. exp. Ther. 108, 410–423 (1953).

    PubMed  CAS  Google Scholar 

  • Farah, A., F. Koda, and M. Fraser: The action of fluoroacetate on the p-aminohippurate uptake by the renal slices of the dog. J. Pharmacol. exp. Ther. 113, 169–177 (1955).

    PubMed  CAS  Google Scholar 

  • Farah, A., T. C. West, and R. Angel: The action of sodium fluoroacetate on intestinal smooth muscle. J. Pharmacol. exp. Ther. 98, 234–244 (1950).

    PubMed  CAS  Google Scholar 

  • Fawaz, G.: Die Wirkung von Fluoressigsäure auf Leistung und Stoffwechsel des Herzlungenpräparates des Hundes. Naunyn-Schmiedebergs Arch. exp. Path. u. Pharmak. 228, 377–386 (1956).

    CAS  Google Scholar 

  • Ferguson, H. G., P. DE Mayo, F. L. M. Pattison, and T. Tabata: The photolysis of some a-substituted cyclohexanones. Canad. J. Chem. 41, 2099–2100 (1963).

    Article  CAS  Google Scholar 

  • Foss, G. L.: The toxicology and pharmacology of methyl fluoroacetate (Mfa) in animals, with some notes on experimental therapy. Brit. J. Pharmacol. 3, 118–127 (1948).

    PubMed  CAS  Google Scholar 

  • Fraser, R. R., J. E. Millington, and F. L. M. Pattison: Toxic fluorine compounds. XV. Some co-fluoro-ß-ketoesters and co-fluoroketones. J. Amer. them. Soc. 79, 1959–1961 (1957).

    Article  CAS  Google Scholar 

  • Fraser, R. R., and F. L. M. Pattison: Ethyl co-fluoroacetoacetate. Nature (Lond.) 176, 696 (1955).

    Article  CAS  Google Scholar 

  • Fried, J. F., M. W. Rosenthal, and J. Schubert: Induced accumulation of citrate in therapy of experimental lead poisoning. Proc. Soc. exp. Biol. (N. Y.) 92, 331–333 (1956).

    Article  CAS  Google Scholar 

  • Furchgott, R. F., and E. Schorr: Sources of energy for intestinal and smooth muscle contractions. Proc. Soc. exp. Biol. (N. Y.) 61, 280–286 (1946).

    Article  CAS  Google Scholar 

  • Gal, E. M.: Studies of enzyme inhibition by fluoromalate and fluoroacetoacetates. Arch. Biochem. 90, 278–287 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Gal, E. M., P. A. Drewes, and N. F. Taylor: The metabolism of fluoroacetic acid 2-C14, in the intact rat. Arch. Biochem. 93, 1–14 (1961).

    Article  PubMed  CAS  Google Scholar 

  • Gal, E. M., A. S. Fairhurst, R. E. Smith, and R. A. Peters: Inhibition of oxidative mechanism by 3-fluoropyruvate. Biochem. biophys. Acta (Amst.) 20, 583–584 (1956).

    Article  CAS  Google Scholar 

  • Gal, E. M., R. A. Peters, and R. W. Wakelin: Some effects of synthetic fluoro compounds on the metabolism of acetate and citrate. Biochem. J. 64, 161–168 (1956).

    PubMed  CAS  Google Scholar 

  • Gillieson, A. H. C. P., and R. A. Newcomb: The application of the hollow cathode source to spectrochemical analysis. Part II. The micro-determination of organically bound fluorine. A.E.R.E. (Harwell) Report C/R 764, Ministry of Supply, Great Britain, 1951.

    Google Scholar 

  • Gitter, S.: The influence of acetamide on citrate accumulation after fluoroacetate poisoning Biochem. J. 63, 182–187 (1956).

    PubMed  CAS  Google Scholar 

  • Gitter, S., I. Blank, and E. D. Bergmann: Organic fluorine compounds. I. Influence of acetamide on fluoroacetate poisoning. Koninkl. Ned. Acad. Wetenschap. Proc. Ser. C. 56, 423–426 (1953).

    CAS  Google Scholar 

  • Glew, D. N., and E. A. Moelwyn-Hughes: The kinetics of the acid and alkaline hydrolysis of methyl fluoride in water. Proc. Roy. Soc., A, 211, 254–265 (1952).

    Article  CAS  Google Scholar 

  • Gordon, R. S., and A. Cherkes: Unesterified fatty acid in human blood plasma. J. clin. Invest. 35, 206–212 (1956).

    Article  PubMed  CAS  Google Scholar 

  • Gotto, A. M., and H. L. Kornberg: Properties of a glycerate-forming enzyme from Pesudomonas ovalis (Chester). Biochem. J. 79, 9 P (1961).

    Google Scholar 

  • Gryszkiewicz-Trochimowski, E., O. Gryszkiewicz-Trochimowski et R. Levy: Recherches sur les composés organiques fluorés dans la série aliphatique. Vii. Note sur la préparation de l’acide monofluoroacétique et sur plusieurs de ses dérivés. Bull. Soc. chim. Fr. 1953, 462–465.

    Google Scholar 

  • Gryszkiewicz-Trochimowski, E., A. Sporzynski et J. Wnuk: Recherches sur les composés organiques fluorés dans la série aliphatique. I. Méthode genérale de préparation des composés organiques fluorés. Rec. Tray. chim. Pays-Bas 66, 413–418 (1947).

    Article  Google Scholar 

  • Hall, R. J.: The determination of microgram amounts of fluorine by diffusion. Analyst. 85, 560–563 (1960).

    Article  CAS  Google Scholar 

  • Hall, R. J.: An apparatus for large scale preparative chromatography with especial application to the separation of a long chain fluoro-fatty acid. J. Chromatogr. 5, 93–97 (1961).

    Article  CAS  Google Scholar 

  • Hall, R. J., and P. F. V. Ward: Unpublished results (1962).

    Google Scholar 

  • Hartman, K.-U., and C. Heidelberger: Studies on fluorinated pyrimidines. Xiii. Inhibition of thymidylate synthetase. J. biol. Chem. 236, 3006–3013 (1961).

    Google Scholar 

  • Hasek, W. R., W. C. Smith, and V. A. Engelhardt: The chemistry of sulfur tetrafluoride. II. The fluorination of organic carbonyl compounds. J. Amer. chem. Soc. 82, 543–551 (1960).

    Article  CAS  Google Scholar 

  • Hastings, A. B., R. A. Peters, and R. W. Wakelin: A study of the influence of the inorganic ion environment on the convulsions induced in pigeons by fluorocitrate. J. Physiol. (Lond.) 120, 50 P (1953).

    Google Scholar 

  • Hastings, A. B., R. A. Peters, and R. W. Wakelin: The effect of subarachnoid injection of fluorocitrate into cerebrospinal fluid of rabbits. Quart. J. exp. Physiol. 40, 258–268 (1955).

    PubMed  CAS  Google Scholar 

  • Hendershot, L. C., and M. B. Chenoweth: Antagonism of three homologous monofluorinated fatty acids by several fatty acids. J. Pharmacol. exp. Ther. 110, 344–351 (1954).

    PubMed  CAS  Google Scholar 

  • Hendershot, L. C., and M. B. Chenoweth: Fluoroacetate and fluorobutyrate convulsions in the isolated cerebral cortex of the dog. J. Pharmacol. exp. Ther. 113, 160–168 (1955).

    PubMed  CAS  Google Scholar 

  • Hoffmann, F. W.: Preparation of aliphatic fluorides. J. Amer. chem. Soc. 70, 2596–2597 (1948).

    Article  CAS  Google Scholar 

  • Hoffmann, F. W.: Aliphatic fluorides. I. w,w’-Difluoroalkanes. J. Org. Chem. 14, 105–110 (1949).

    Article  CAS  Google Scholar 

  • Hoffmann, F. W.: Aliphatic fluorides. II. 1-Halogeno-w-fluoroalkanes. J. Org. Chem. 15, 425–434 (1950).

    Article  CAS  Google Scholar 

  • Horiuchi, N.: C—F bond rupture in monofluoroacetate. Seikagaku 34, 92–98 (1962 a). [J. Jap. Biochem. Soc., in Japanese.]

    Google Scholar 

  • Horiuchi, N.: Studies on the rupture activity in the animal body to the C—F bond of Fch2Coona. Kogyo Kagaku Zasshi 65, 1177–1179 (1962b). [J. Chem. Soc. Japan, Ind. Chem. Section, in Japanese.]

    Google Scholar 

  • Howell, W. C., W. J. Cott, and F. L. M. Pattison: Organometallic reactions of w-fluoroalkylmagnesium chlorides. II. Reactions of w-fluoroalkylmagnesium chlorides. J. Org. Chem. 22, 255–259 (1957).

    Article  CAS  Google Scholar 

  • Howell, W. C., J. E. Millington, and F. L. M. Pattison: Toxic fluorine compounds. Vii. w-Fluoroalkyl thiocyanates and w-fluoroalkyl mercaptans. J. Amer. them. Soc. 78, 3843–3846 (1956).

    Article  CAS  Google Scholar 

  • Hudlicki, M.: Organic compounds of fluorine. II. Fluorinated amino acids. Coll. Czech. Chem. Comm. 26, 1414–1421 (1961).

    Google Scholar 

  • Hudlicki, M.: Chemistry of Organic Fluorine Compounds. New York: MacMillan 1962.

    Google Scholar 

  • Hughes, G. M. K., and B. C. Saunders: Studies in peroxidase action. Part IX. Reactions involving the rupture of the C—F, C—Br and C—I links in aromatic amines. J. them. Soc. 1954, 4630–4634.

    Google Scholar 

  • Hutchens, J. O., H. Wagner, B. Podolsky, and T. M. Mcmahon: The effect of ethanol and various metabolites on fluoroacetate poisoning. J. Pharmacol. exp. Ther. 95, 62–70 (1949).

    PubMed  CAS  Google Scholar 

  • Iciiihara, A., K. Adachi, K. Hosokawa, and Y. Takeda: The enzymatic hydroxylation of aromatic carboxylic acids; substrate specificities of anthranilate and benzoate oxidases. J. biol. Chem. 237, 2296–3202 (1962).

    Google Scholar 

  • Inman, C. E., R. E. Oesterling. and E. A. Tyczkowski: Reactions of perchloryl fluoride with organic compounds. II. Fluorination of certain active methylene compounds. J. Amer. them. Soc. 80, 6533–6535 (1958).

    Article  CAS  Google Scholar 

  • Jarrett, J. G., and A. Packham: Response of the sheep to sublethal doses of fluoroacetate. Nature (Lond.) 177, 580–581 (1956).

    Article  CAS  Google Scholar 

  • Jayasuriya, G. C. N.: Citrate accumulation from glycollate by an oxalate-decomposing organism Biochem. J. 56, xli (1954);

    Google Scholar 

  • Jayasuriya, G. C. N.: Citrate accumulation from glycollate by an oxalate-decomposing organism Biochem. J. 58, xxxi (1954).

    Google Scholar 

  • Jayasuriya, G. C. N.: The oxidative properties of an oxalate-decomposing organism, Pseudomonas Odi with particular reference to the synthesis of citrate from glycollate. Biochem. J. 64, 469–477 (1956).

    PubMed  CAS  Google Scholar 

  • Jenkins, R. L., and H. C. Koehler: Making 1080 safe. A case study in the safe manufacture and distribution of a hazardous chemical. Chem. Ind. 62, 232–235 (1948).

    Google Scholar 

  • Judah, J. D., and K. R. Rees: Activation of fatty acid oxidation by kidney and liver mitochondria. Biochem. J. 55, 664–668 (1953).

    PubMed  CAS  Google Scholar 

  • Judah, J. D., and K. R. Rees: A note on the action of fluoroacetate. Biochem. J. 57, 374–376 (1954).

    PubMed  CAS  Google Scholar 

  • Kacser, H.: The stereochemical relations of the four fluorocitrate isomers. Disc. Faraday Soc. 20, 283–286 (1955).

    Google Scholar 

  • Kalnitsky, G., and E. S. G. Barron: The effect of fluoroacetate on the metabolism of yeast and bacteria. J. biol. Chem. 170, 83–95 (1947).

    CAS  Google Scholar 

  • Kandel, A., and M. B. Crenoweth: Metabolic disturbances produced by some fluoro fatty acids: relation to the pharmacologic activity of these compounds. J. Pharmacol. exp. Ther. 104, 234–247 (1952a).

    PubMed  CAS  Google Scholar 

  • Kandel, A., and M. B. Crenoweth: Tolerance to fluoroacetate and fluorobutyrate in rats. J. Pharmacol. exp. Ther. 104, 248–252 (1952b).

    PubMed  CAS  Google Scholar 

  • Kent, P. W., G. Hebblethwaite, and N. F. Taylor: Fluorocarbohydrates. Part II. Characterization of (+)-2-deoxy-2-fluoroglyceric acid and its quinine salts. J. them. Soc. 1960, 106–108.

    Google Scholar 

  • Kilby, B. A., and K. J. Carpenter: Unpublished report (1944).

    Google Scholar 

  • Kirschner, K., V. Henning, and F. Lynen: Zur Biosynthese der Terpene. Xiii Die Hemmung der biologischen Squalensynthese durch 2-Fluormevalonsäure. Ann. 644, 48–64 (1961).

    Google Scholar 

  • Knunyants, I. L., O. V. Kildisheva, and E. Bykhovskaya: The reaction of aliphatic oxides with hydrogen fluoride. II. J. Gen. Chem. U.S.S.R. 19, 93–103 (1949a) [Engl. translation].

    Google Scholar 

  • Knunyants, I. L., O. V. Kildisheva, and I. P. Petrov: The reaction of aliphatic oxides with hydrogen fluoride. I. J. Gen. Chem. U.S.S.R. 19, 87–91 (1949b) [Engl. translation].

    Google Scholar 

  • Knunyants, I. L., Va. M. Kisel, and E. G. Bykhovskaya: Reaction of hydrogen fluoride with diazo ketones. Izvest. Akad. nauk. S.S.S.R., Otdel. Khim. nauk, 377–378 (1956) [Russ.].

    Google Scholar 

  • Knunyants, I. L., and G. A. Soxolsxll: A new rearrangement of trihaloacetohydroxamic acids. Doklady Akad. Nauk S.S.S.R. 132, 602–605 (1960) [Russ.]. Chem. Abstracts 54, 24366 g (1960).

    Google Scholar 

  • Kochmann, M.: Inhalation anesthesia. In Heffter’S Handbuch der exp. Pharm. 1, 133–261 (1923).

    Google Scholar 

  • Kornberg, H. L., and S. R. Elsden: The metabolism of 2-carbon compounds by microorganisms. Advanc. Enzymol. 23, 401–470 (1961).

    CAS  Google Scholar 

  • Krasna, A. I.: The inhibition of fumarase and malic dehydrogenase by DL-ß-fluoromalic acid. J. biol. Chem. 236, 749–753 (1961).

    PubMed  CAS  Google Scholar 

  • Krasna, A. I.: The stereochemical configuration of ni,-ß-fluoromalic acid. J. biol. Chem. 237, 1418–1420 (1962).

    PubMed  CAS  Google Scholar 

  • Kumler, W. D., E. KuN, and J. N. Shoolery: The enolization of oxaloacetic acid, diethyl oxaloacetate and diethyl fluorooxaloacetate as determined by Nmr analyses. J. Org. Chem. 27, 1165–1167 (1962).

    CAS  Google Scholar 

  • Kun, E., D. W. Fanshier, and D. R. Grassetti: Interaction between 13-fluorooxaloacetate and glutamate-aspartate transaminase of heart mitochondria. J. biol. Chem. 235, 416–419 (1960).

    PubMed  CAS  Google Scholar 

  • Kun, E., D. R. Grassetti, D. W. Fanshier, and R. M. Featherstone: The reaction of malic dehydrogenase with a-keto-ß-fluorosuccinic (fi-fluoro-oxaloacetic) acid. Biochem. Ph armacol. 1, 207–212 (1959).

    Article  Google Scholar 

  • Kun, E., and H. G. Williams-Ashman: The influence of fl-fluoro-oxaloacetate on the malate dehydrogenase (decarboxylating). Biochem. biophys. Acta (Amst) 59, 719–722 (1962).

    Article  CAS  Google Scholar 

  • Lang, S.: Über die Umwandlung des Acetonitrils und seiner Homologen im Thierkörper. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 34, 247–258 (1894).

    Google Scholar 

  • LA Zerte, J. D., D. A. Rausch, R. J. KosHar, J. D. Park, W. H. Pearlson, and J. R. Lacher: Perfluoroacrylonitrile and its derivatives. J. Amer. them. Soc. 78, 5639–5641 (1956).

    Article  Google Scholar 

  • LiebÉCQ, C., and R. A. Peters: The toxicity of fluoroacetate and the tricarboxylic acid cycle. Biochim. biophys. Acta (Amst) 3, 215–230 (1949).

    Article  Google Scholar 

  • Lindenbaum, W., M. R. White, and J. Schubert: Citrate formation in vivo induced by non-lethal doses of fluoroacetate. J. biol. Chem. 190, 585–593 (1951).

    PubMed  CAS  Google Scholar 

  • Lotspeich, W. D., R. A. Peters, and T. H. Wilson: The inhibition of aconitase by “inhibitor fractions” isolated from tissues poisoned with fluoroacetate. Biochem. J. 51, 20–25 (1952).

    PubMed  CAS  Google Scholar 

  • Lowenstein, J. M.: See Kornacker, M., and J. M. Lowenstein: The relation between the rates of citrate cleavage and fatty acid synthesis in rat liver preparations. Biochem. J. 89, 27 P (1963).

    Google Scholar 

  • Mager, J., and I. Blank: Synthesis of fluoropyruvic acid and some of its biological properties. Nature (Lond.) 173, 126 (1954).

    Article  CAS  Google Scholar 

  • Mager, J., J. Goldblum-Sinai, and I. Blank: Effect of fluorocitric acid and allied fluoroanalogues on the growth of Escher. coli. J. Bact. 70, 320–325 (1955).

    CAS  Google Scholar 

  • Marais, J S C: The isolation of the toxic principle “potassium cymonate” from “Gifblaar,” Dichapetalum cymosum (Hook) Engl. Onderstepoort J. Vet. Sci. Animal Ind. 18, 203–206 (1943).

    CAS  Google Scholar 

  • Marais, J S C: Monofluoroacetic acid, the toxic principle of “Gifblaar,” Dichapetalum cymosum (Hook) Engl. Onderstepoort J. Vet. Sci. Animal Ind. 20, 67–73 (1944).

    CAS  Google Scholar 

  • Marcus, A., and W. B. Elliott: Enzymatic reactions of fluoroacetate and fluoroacetyl coenzyme A. J. biol. Chem. 218, 823–830 (1956).

    PubMed  CAS  Google Scholar 

  • Marcus, A., and W. B. Elliott: Fluoroacetyl phosphate; preparation and properties. J. Amer. chem. Soc. 80, 4287–4291 (1958).

    Article  CAS  Google Scholar 

  • Martius, C.: Über den Abbau der Citronensäure. Z. physiol. Chem. 247, 104–110 (1937).

    CAS  Google Scholar 

  • Martius, C.: Der intermediare Stoffwechsel der Citronensäure. Z. physiol. Chem. 257, 29–42 (1938).

    CAS  Google Scholar 

  • Martius, C.: Über die Unterbrechung des Citronensäure-Cyklus durch Fluoressigsäure. Ann. 561, 227–232 (1949).

    CAS  Google Scholar 

  • Mcbee, E. T., O. R. Pierce, H. W. Kilbourne, and E. R. Wilson: The preparation and reactions of fluorine-containing acetoacetic esters. J. Amer. chem. Soc. 75, 3152–3153 (1953).

    Article  CAS  Google Scholar 

  • Meuler, A H, and Y. T. Chang: Biological reactions of fluoroacetyl choline. Arch. Biochem. 62, 293–298 (1956).

    Article  Google Scholar 

  • Meldrum, G. K., J. T. Bignell, and I. Rowley: The use of fluoroacetate (compound 1080) for the control of the rabbit in Tasmania. Austral. Vet. J. 33, 186–196 (1957).

    Article  CAS  Google Scholar 

  • Miller, D. P., and H. W Haggard: Intracellular penetration of bromide as a feature in the toxicity of alkyl bromides. J. industr. Hyg. 25, 423–433 (1943).

    CAS  Google Scholar 

  • Millington, J. E., G. M. Brown, and F. L. M. Pattison: Toxic fluorine compounds. Viii. co-Fluoroalkanesulfonyl chlorides and fluorides. J. Amer. chem. Soc. 78, 3846–3847 (1956).

    Article  CAS  Google Scholar 

  • Millington, J. E., and F. L. M. Pattison: Toxic fluorine compounds. Xii. Esters of w-fluoroalcohols. Canad. J. Chem. 34, 1532–1541 (1956).

    Article  CAS  Google Scholar 

  • Mirosevic-Sorgo, P., and B. C. Saunders: Toxic fluorine compounds containing the C—F link X Rupture of the C—F link by alkali and other reagents. Tetrahedron 5, 38–43 (1959).

    Article  Google Scholar 

  • Miura, K., and T. Hori: Studies on the metabolism of fluoroacetate in the liver of a rat. Part II. Isolation and identification of monofluoroacetone bodies. Agr. biol. Chem. (Tokyo) 25, 94–99 (1961).

    CAS  Google Scholar 

  • Miura, K., S. Otsuka, and K. Honda: Studies on the abnormal metabolism in animals poisoned with sodium fluoroacetate. Bull. Agric. Chem. Soc. (Japan) 20, 219–222 (1956).

    Article  CAS  Google Scholar 

  • Miura, K., T. Uchiyama, and K. Honda: Studies on the metabolism of monofluoroacetate in the liver of a frog. Agr. biol. Chem. (Tokyo) 25, 83–87 (1961).

    CAS  Google Scholar 

  • Morrison, J. F.: The purification of aconitase. Biochem. J. 56, 99–105 (1954).

    PubMed  CAS  Google Scholar 

  • Miura, K., and R. A. Peters: Biochemistry of fluoroacetate poisoning: the effect of fluorocitrate on purified aconitase. Biochem. J. 58, 473–479 (1954).

    Google Scholar 

  • Mullin, F. J., A. B. Hastings, and W. M. Lees: Neuromuscular responses to variations in calcium and potassium concentrations in the cerebrospinal fluid. Amer. J. Physiol. 121, 719–727 (1938).

    CAS  Google Scholar 

  • Murray, L. R., J. D. McConnell, and J. H. Whittem: Suspected presence of fluoroacetate in Acacia georginae, F. M. Bailey. Aust. J. Sci. 24, 41–42 (1961).

    Google Scholar 

  • Nair, P. V., and H. Busch: Improved synthesis of monofluoro-and monochloropyruvic acids. J. org. Chem. 23, 137–139 (1958).

    Article  CAS  Google Scholar 

  • Newman, M. S., M. W. Renoll, and I. Auerbach: Synthesis and reduction of difluorodecanoic acid derivatives. J. Amer. chem. Soc. 70, 1023–1024 (1948).

    Article  CAS  Google Scholar 

  • Newton, J., and F. L. M. Pattison: Unpublished results, 1961.

    Google Scholar 

  • O’Brien, R. D., and R. A. Peters: The biochemistry of 2-deoxy-2-fluoro-DL-glyceraldehyde with a note on the toxicity of 2-deoxy-2-fluoroglycerol. Biochem. Pharmacol. 1, 1–18 (1958 a).

    Google Scholar 

  • O’Brien, R. D., and R. A. Peters: The metabolism of DL-1-deoxy-1-fluoroglycerol. Biochem. J. 79, 188–195 (1958b).

    Google Scholar 

  • Oelrichs, P. B., and T. Mcewan: Isolation of the toxic principle in Acacia georginae. Nature (Lond.) 190, 808–809 (1961).

    Article  CAS  Google Scholar 

  • Oelrichs, P. B., and T. McEwan: The toxic principle of Acacia georginae. Queensland J. Agric. Sci. 19, 1–16 (1962).

    CAS  Google Scholar 

  • Olaa, G. A.: Unpublished results, cited in: G. A. Olah, Ed. Friedel-Crafts and related reactions, Vol. I, 40. New York: Interscience Publishers 1963.

    Google Scholar 

  • Olah, G., u. S. Kuhn: Darstellung und Untersuchung organischer Fluorverbindungen. Xxi Darstellung von Fluoracetaldehyd und aliphatischen Fluormethylketonen. Chem. Ber. 89, 864–865 (1956).

    Article  CAS  Google Scholar 

  • Oliveira, M. M.: Chromatographic isolation of monofluoroacetic acid from Palicourea marcgravii St. Hil. Experientia 19, 586–587 (1963).

    Article  Google Scholar 

  • O’Neill, G. J., and F. L. M. Pattison: Toxic fluorine compounds. Xiv. Some w-fluoroalkyl nitrogen compounds. J. Amer. them. Soc. 79, 1956–1958 (1957).

    Article  Google Scholar 

  • Ord, M. C., and L. A. Stocken: Sex differences in effect of radiation and fluoroacetate poisoning on liver metabolism. Proc. Soc. exp. Biol. (N. Y.) 83, 695–697 (1953).

    Article  CAS  Google Scholar 

  • Parker, J. M., and I. G. Walker: A toxicological and biochemical study of co-fluoro compounds. Canad. J. Biochem. 35, 407–417 (1957).

    Article  PubMed  CAS  Google Scholar 

  • Parker, R. E.: Mechanisms of fluorine displacement. In: M. Stacey, J. C. Tatlow and A. G. Sharpe, Eds. Advances in Fluorine Chemistry, Vol. 3, 63–91. London: Butterworths 1963.

    Google Scholar 

  • Pattison, F. L. M.: Toxic fluorine compounds. I. Nature (Lond.) 172, 1139–1141 (1953).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M.: Toxic fluorine compounds. II. Nature (Lond.) 174, 737–741 (1954).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M.: From war to peace: toxic aliphatic fluorine compounds. Chem. Canada 9, 27–33 (1957).

    CAS  Google Scholar 

  • Pattison, F. L. M.: Toxic Aliphatic Fluorine Compounds. Amsterdam: Elsevier 1959.

    Google Scholar 

  • Pattison, F. L. M.: Unpublished results, 1962.

    Google Scholar 

  • Pattison, F. L. M., W. J. Cott, and W. C. Howell: Organometallic reactions of w-fluoroalkyl halides. Iii. w-Fluoroalkyllithium compounds. J. org. Chem. 22, 464–465 (1957).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., W. J. Cott, and R. W. White: Toxic fluorine compounds. V. w-Fluoronitriles and w-fluorow’-nitroalkanes. J. Amer. chem. Soc. 78, 3484–3487 (1956).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., and R. E. A. Dear: Synthesis of the toxic principle of Dichapetalum toxicarium (18-fluorocis-9-octadecenoic acid). Nature (Lond.) 192, 1284–1285 (1961).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., R. R. Fraser, E. J. Middleton, J. C. Schneider, and J. B. Stothers: Esters of fluoro-acetic acid and of 2-fluoroethanol. Canad. J. Technol. 34, 21–28 (1956).

    CAS  Google Scholar 

  • Pattison, F. L. M., R. R. Fraser, G. J. O’Neill, and J. F. K. Wilshire: Toxic fluorine compounds. X. w-Fluorocarboxylic acid chlorides, anhydrides, amides and anilides. J. org. Chem. 21, 887–889 (1956).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., and W. C. Howell: Toxic fluorine compounds. IV. co-Fluoroalkyl halides. J. org. Chem. 21, 748–753 (1956a).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., and W. C. Howell: Organometallic reactions of co-fluoroalkyl halides. I. Preparation of w-fluoroalkylmagnesium halides. J. org. Chem. 21, 879–882 (1956b).

    CAS  Google Scholar 

  • Pattison, F. L. M., W. C. Howell, A. J. Mcnamara, J. C. Schneider, and J. F. Walker. Toxic fluorine compounds. Iii. w-Fluoroalcohols. J. org. Chem. 21, 739–747 (1956).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., W. C. Howell, and R. W. White: Toxic fluorine compounds. VI. co-Fluoroalkylamines. J. Amer. chem. Soc. 78, 3487–3489 (1956).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., W. C. Howell, and R. G. Woolford: Toxic fluorine compounds. Xiii. w-Fluoroalkyl ethers. Canad. J. Chem. 35, 141–148 (1957).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., S. B. D. Hunt, and J. B. Stothers: Toxic fluorine compounds. IX. w-Fluorocarboxylic esters and acids. J. org. Chem. 21, 883–886 (1956).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., and J. E. Millington: The preparation and some cleavage reactions of alkyl and substituted alkyl methanesulphonates. Canad. J. Chem. 34, 757–768 (1956).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., and J. J. Norman: Toxic fluorine compounds. Xvii. Some 1-fluoroalkanes, co-fluoroalkenes and w-fluoroalkynes. J. Amer. chem. Soc. 79, 2311–2316 (1957).

    Article  Google Scholar 

  • Pattison, F. L. M., and B. C. Saunders: Toxic fluorine compounds containing the C—F link. Part Vii. Evidence for the ß-oxidation of w-fluoro-carboxylic acids in vivo. J. chem. Soc. 1949, 2745–2749.

    Google Scholar 

  • Pattison, F. L. M., J. B. Stothers, and R. G. Woolford: Anodic syntheses involving w-monohalocarboxylic acids. J. Amer. chem. Soc. 78, 2255–2259 (1956).

    Article  Google Scholar 

  • Pattison, F. L. M., and R. G. Woolford: (+)-18-Fluoro-l0-methyloctadecanoic acid (Fluorotuberculostearic acid). J. Amer. chem. Soc. 79, 2306–2308 (1957a).

    Article  CAS  Google Scholar 

  • Pattison, F. L. M., and R. G. Woolford: Toxic fluorine compounds. Xvi. Branched w-fluorocarboxylic acids. J. Amer. chem. Soc. 79, 2308–2311 (1957b).

    Article  CAS  Google Scholar 

  • Peeters, G., R. Coussens, and G. Sierins: Metabolism of fatty acids in the isolated and perfused bovine mammary gland. Intern. Colloquium Bioch. Problems Lipiden. 293–298 (1953).

    Google Scholar 

  • Peeters, G., R. Coussens, and G. Sierins: Sodium monofluoroacetate and the isolated lactating cow udder. Arch. int. Pharmacodyn. 98, 288–301 (1954).

    CAS  Google Scholar 

  • Peters, R. A.: Lethal synthesis. [Croonian lecture.] Proc. roy. Soc. B, 139, 143–170 (1952).

    CAS  Google Scholar 

  • Peters, R. A.: Dohme Lectures. Biochemistry of some toxic agents. Bull. Johns Hop. Hosp. 97, 1–42 (1955).

    CAS  Google Scholar 

  • Peters, R. A.: Mechanism of the toxicity of the active constituent of Dichapetalum cymosum and related compounds. Advanc. Enzymol. 18, 113–159 (1957).

    CAS  Google Scholar 

  • Peters, R. A.: The comparison of the effect of an odd and even unsaturated fluorofatty acid on kidney particles. Biochem. Pharmacol. 1, 354–355 (1958).

    Article  Google Scholar 

  • Peters, R. A.: Further experiments on the inhibition of aconitase by enzymically prepared fluorocitric acid. Biochem. J. 79, 261–268 (1961).

    PubMed  CAS  Google Scholar 

  • Peters, R. A.: Biochemical lesions and lethal synthesis, pp. 1–132 (p. 113 ). Oxford: Pergamon Press 1963.

    Google Scholar 

  • Peters, R. A.: Applications of chemical defence research in medicine. Edinb. med. J. 48, 197–213 (1951).

    Google Scholar 

  • Peters, R. A., and R. J. Hall: Note upon the reaction of fluoropyruvate with some —Sii substances. Biochim. biophys. Acta (Amst) 26, 433–439 (1957).

    Article  CAS  Google Scholar 

  • Peters, R. A., and R. J. Hall: Further observations upon the toxic principle of Dichapetalum toxicarium. Biochem. Pharmacol. 2, 25–36 (1959).

    Article  CAS  Google Scholar 

  • Peters, R. A., and R. J. Hall: Fluorine compounds in Nature; the distribution of carbon — fluorine compounds in some species of Dichapetalum. Nature (Lond.) 187, 573–575 (1960a).

    Article  CAS  Google Scholar 

  • Peters, R. A., and R. J. Hall: The toxicity to rabbits and some other animals of the fluorofatty acid present in the seeds of Dichapetalum toxicarium. J. Sci. Food Agr. 1960b, 608–612.

    Google Scholar 

  • Peters, R. A., R. J. Hall, P. F. V. Ward, and N. Sheppard: The chemical nature of the toxic compounds containing fluorine in the seeds of Dichapetalum toxicarium. Biochem. J. 77, 17–23 (1960).

    PubMed  CAS  Google Scholar 

  • Peters, R. A., and M. Shorthouse: Unpublished results, 1962.

    Google Scholar 

  • Peters, R. A., and R. W. Wakelin: Pyruvate oxidate system in brain tissue. J. Physiol. (Lond.) 119, 421–427 (1953).

    CAS  Google Scholar 

  • Peters, R. A., and R. W. Wakelin: Synthesis of fluorocitric acid and its inhibition in acetate. Biochem. J. 67, 280–286 (1957).

    PubMed  CAS  Google Scholar 

  • Peters, R. A., R. W. Wakelin, A. J. P. Martin, J. Webb, and F. T. Birks: Observations upon the toxic principle in the seeds of Dichapetalum toxicarium. Separation of a long chain fatty acid containing fluorine. Biochem. J. 71, 245–248 (1959);

    PubMed  CAS  Google Scholar 

  • Peters, R. A., R. W. Wakelin, A. J. P. Martin, J. Webb, and F. T. Birks: Observations upon the toxic principle in the seeds of Dichapetalum toxicarium. Separation of a long chain fatty acid containing fluorine. Biochem. J. 58, xl (1954).

    Google Scholar 

  • Peters, R. A., R. W. Wakelin, P. Buffa, and L. C. Thomas: Biochemistry of fluoroacetate poisoning. The isolation and some properties of the fluorotricarboxylic acid inhibitor of citrate metabolism. Proc. roy. Soc. (Lond.) B, 140, 497–507 (1953).

    Article  CAS  Google Scholar 

  • Peters, R. A., R. W. Wakelin, and A. B. Hastings: Proc. xix. Inter. Congress of Physiology. p. 674 (1953).

    Google Scholar 

  • Peters, R. A., R. W. Wakelin, D. E. A. Rivett, and L. C. Thomas: Fluoroacetate poisoning: comparison of synthetic fluorocitric acid with the enzymically synthesized fluorotricarboxylic acid. Nature (Lond.) 171, 1111–1112 (1953).

    Article  CAS  Google Scholar 

  • Phillips, A. H., and R. G. Langdon: Incorporation of monofluoroacetic acid into the nonsaponifiable lipids of the rat liver. Arch. Biochem. Biophys. (Amst.) 58, 247–249 (1955).

    Article  CAS  Google Scholar 

  • Potter, V. R., and H. Busch: Citric acid content of normal and tumor tissues in vivo following injection of fluoroacetate. Cancer Res. 10, 353–356 (1950).

    PubMed  CAS  Google Scholar 

  • Power, F. B., and F. Tutin: Chemical and physiological examination of the fruit of Chailletia toxicaria (A West African poison). J. Amer. chem. Soc. 28, 1170–1183 (1906).

    Article  CAS  Google Scholar 

  • Pscheidt, G. R., D. Benitez, L. B. Kirschner, and W. E. Stone: Effects of fluoroacetate poisoning on citrate, lactate and energy-rich phosphates in the cerebrum. Amer. J. Physiol. 176, 483–487 (1954).

    PubMed  CAS  Google Scholar 

  • Pucher, G. W., C. C. Sherman, and H. B. Vickery: A method to determine small amounts of citric acid in biological material. J. biol. Chem. 113, 235–245 (1936).

    CAS  Google Scholar 

  • Raasch, M. S.: a,a-Difluoro-substituted acids of the tricarboxylic acid cycle, their salts, amides and esters. U.S. Patent 2,824,888 February 25 (1958).

    Google Scholar 

  • Raasch, M. S.: 5-Fluoronorvaline and 6-fluoronorleucine. J. org. Chem. 23, 1567–1568 (1958).

    Article  CAS  Google Scholar 

  • Reilly, J., W. F. Riker, W. C. Whitehouse, and K. Kurzaki: The action of methyl fluoroacetate on the papillary muscle of the cat with comparative experiments on the action of methyl chloroacetate. J. Pharmacol. exp. Ther. 108, 393–409 (1953).

    PubMed  CAS  Google Scholar 

  • Renner, W.: A case of poisoning by the fruit of Chailletia toxicaria (ratsbane). Brit. med. J. 1904 I, 1314.

    Google Scholar 

  • Rimington, C.: Chemical investigation of the Gifblaar, Dichapetalum cymosum (Hook) Engl. 1. Onderstepoort J. Vet. Sci. Animal Indust. 5, 81 (1935).

    CAS  Google Scholar 

  • Rivett, D. E. A.: The synthesis of monofluorocitric acid. J. chem. Soc. 1953, 3710–3711.

    Google Scholar 

  • Rose, I. A., M. Greenberg-Manago, S. R. Korey, and S. OcHoA: Enzymatic phosphorylation of acetate. J. biol. Chem. 211, 737–756 (1954).

    PubMed  CAS  Google Scholar 

  • Rothstein, A.: Symposia Soc. Exp. Biol. No. viii, pp. 165–201. Cambridge: Univ. Press 1954.

    Google Scholar 

  • Saunders, B. C.: Toxic properties of w-fluoro-carboxylic acids and derivatives. Nature (Lond.) 160, 179–181 (1947).

    Article  CAS  Google Scholar 

  • Saunders, B. C.: Phosphorus and fluorine, p. 212. Cambridge: Univ. Press 1957.

    Google Scholar 

  • Saunders, B. C., and G. J. Stacey: Toxic fluorine compounds containing the C—F link. Part I. Methyl fluoroacetate and related compounds. J. chem. Soc. 1948, 1773–1779.

    Google Scholar 

  • Saunders, B. C., and G. J. Stacey: Toxic fluorine compounds containing the C—F link Part IV. (a) 2-Fluoroethyl fluoro-acetate and allied compounds. (b) 2: 2’-Difluorodiethyl ethylene dithioglycol ether. J. chem. Soc. 1949, 916–919.

    Google Scholar 

  • Saunders, B. C., and G. J. Stacey, and I. G. E. Wilding: Toxic fluorine compounds containing the C—F link. Part II. 2-Fluoroethanol and its derivatives. J. chem. Soc. 1949, 773–777.

    Google Scholar 

  • Salle, J.: Sur les propriétés du bromure de fluoroacétylcholine (F.Ach). Arch. int. Pharmacodyn. 91, 339–349 (1952).

    CAS  Google Scholar 

  • Schmidt, G., u. H. Jahn: Synthese der a-Fluor-mevalonsäure. Ann. 644, 43–47 (1961).

    CAS  Google Scholar 

  • Singer, F. M., J. P. Januszka, and A. Borman: New inhibitors of in vitro conversion of acetate and mevalonate to cholesterol. Proc. Soc. exp. Biol. (N. Y.) 102, 370–373 (1959).

    Article  CAS  Google Scholar 

  • Steyn, D. G.: Gifblaar poisoning. A summary of our present knowledge in respect of poisoning by Dichapetalum cymosum. 13th and 14th Reports of the Director of Veterinary Education and Research (Onderstepoort Laboratories), Part I, 187–194 (1928).

    Google Scholar 

  • Stickland, R. G.: Some properties of the malic enzyme of pigeon liver. (1) Conversion of malate into pyruvate. (2) Synthesis of malate from pyruvate. Biochem. J. 73, 646–659 (1959).

    PubMed  CAS  Google Scholar 

  • Stoner, H. B.: The mechanism of toxic hepatic necrosis. Brit. J. exp. Path. 37, 176–198 (1956).

    PubMed  CAS  Google Scholar 

  • Swarts, F.: Sur l’acide fluoroacétique. Bull. Acad. roy. Belg. [3] 31, 675–688 (1896).

    Google Scholar 

  • Taylor, N. F., and P. W. Kent: Synthesis of (+) methyl fluoromalate. Nature (Lond.) 174, 401 (1954).

    Article  CAS  Google Scholar 

  • Taylor, N. F., and P. W. Kent: The synthesis of 2-deoxy-2-fluorotetritols and 2-deoxy-2-fluoro-(+)-glyceraldehyde. J. chem. Soc. 1956, 2150–2154.

    Google Scholar 

  • Taylor, N. F., and P. W. Kent: Fluorocarbohydrates. I. The synthesis of 6-deoxy-6-fluoro-a-n-galactose and 5-deoxy5-fluoro-aß-n-ribose. J. chem. Soc. 1958, 872–875.

    Google Scholar 

  • Taylor, T. G.: A modified procedure for the microdetermination of citric acid. Biochem. J. 54, 48–49 (1953).

    PubMed  CAS  Google Scholar 

  • Terner, C.: The metabolism of citric acid in the mammary gland. The effect on the synthesis of citric acid in fluoroacetate-blocked homogenates. Biochem. J. 60, 95–101 (1955).

    PubMed  CAS  Google Scholar 

  • Theiler, A.: Quoted by Steyn, D. G. 1928 (q.v.) (1902).

    Google Scholar 

  • Tourtellotte, W. W., and J. M. Coon: Treatment of fluoroacetate poisoning in mice and dogs. J. Pharmacol. exp. Ther. 101, 82–91 (1951).

    PubMed  CAS  Google Scholar 

  • Tourtellotte, W. W., and J. M. Coon: Synergistic effect of sodium acetate and ethanol in antagonizing sodium fluoroacetate (1080) poisoning in mice. Fed. Proc. 8, 339 (1949).

    Google Scholar 

  • Treble, D. H.: The metabolism of 2-fluoroethanol. Biochem. J. 82, 129–134 (1962).

    PubMed  CAS  Google Scholar 

  • Treble, D. H., and R. A. Peters: The metabolism of 2-deoxy-2-fluoroglyceraldehyde. Biochem. J. 80, 15–16 P (1961).

    Google Scholar 

  • Treble, D. H., and R. A. Peters: Metabolism of 2-deoxy-2-fluoroglyceraldehyde. Biochem. Pharmacol. 11, 891–899 (1962).

    Article  PubMed  CAS  Google Scholar 

  • Tschesche, R., u. H. Machleidt: Synthesen von substituierten ß-Hydroxy-ß-methyl-glutarsäuren und Mevalonsäuren. Ann 631, 61–76 (1960).

    CAS  Google Scholar 

  • Tullock, C. W., and D. D. Coffman: Synthesis of fluorides by metathesis with sodium fluoride. J. org. Chem. 25, 2016–2019 (1960).

    Article  CAS  Google Scholar 

  • VooNG, Sing-TuH, and Ten-Chang Chiang: Syntheses and polymerization of several a-fluoromethylvinyl monomers. Hua Hsüeh Hsüeh Pao 24, 155–161 (1958) [Chinese]. Chem. Abstracts 53, 6064 (1959).

    Google Scholar 

  • Walker, I. G., and J. M. Parker: Further toxicological and biochemical studies on co-fluoro compounds. Canad. J. Biochem. 36, 339–345 (1958).

    PubMed  CAS  Google Scholar 

  • Ward, P. F. V., and R. A. Peters: The chemical and biochemical properties of fluorocitric acid. Biochem. J. 78, 661–668 (1961).

    PubMed  CAS  Google Scholar 

  • Weeks, J R, and M. B. Chenoweth: Separation by fluoroacetate of energy sources for smooth muscle contraction. Fed. Proc. 8, 345 (1949).

    Google Scholar 

  • Whittem, J. H.: Communication with L. R. Murray to Austral. Vet. Assoc. Annual Conf., May 1963.

    Google Scholar 

  • Wilshire, J. F. K., and F. L. M. Pattison: Toxic fluorine compounds. XI. w-Fluoroaldehydes. J. Amer. chem. Soc. 78, 4996–4998 (1956).

    Article  CAS  Google Scholar 

  • Wolleman, W., and G. Feuer: Die Entstehung von Fluorazetyl-Coenzyme A und Fluorazetylcholin aus Fluoressigsäure und Fluorozitronensäure in Gehirnextracten. Acta physiol. Hung. Acad. Sci. 11, 165–171 (1957).

    Google Scholar 

  • Yarovenko, N. N., and M. A. Raksha: Fluorination by means of oc-fluorinated amines. J. Gen. Chem. U.S.S.R. 29, 2125–2128 (1959) [Engl. translation].

    Google Scholar 

  • Yüan, ChÊng-Yeh, Chun-NienChang, and I-FangYeh: Chemotherapy of cancer. Iii. Synthesis of fluorine-containing amino acids. Yao Hsüeh Hsüeh Pao 7, 237–244 (1959) [Chinese]. Chem. Abstracts 54, 12096 (1960).

    Google Scholar 

Addendum

  • Amin, J. H., J. Newton, and F. L. M. Pattison: A new synthesis of alkyl fluorides. The pyrolysis of 2-alkylpseudouronium fluorides and fluoroborates. Canad. J. Chem. 43, 3173–3177 (1965).

    Article  CAS  Google Scholar 

  • Buchanan, R. L., and F. L. M. Pattrsox: Preparation of a-fluoro-y-aminoacids. Canad. J. Chem. 43, 3466–3468 (1965).

    Article  CAS  Google Scholar 

  • Fanshier, D. W., L. K. Gottwald, and E. Kux: Studies on specific enzyme inhibitors. VI. Characterization and mechanism of action of the enzyme-inhibiting isomer of monofluorocitrate. J. biol. Chem. 239, 425–435 (1964).

    PubMed  CAS  Google Scholar 

  • Lahiri, S, and J. H. Quastel: Fluoroacetate and the metabolism of ammonia in the brain. Biochem. J. 89, 157–163 (1963).

    PubMed  CAS  Google Scholar 

  • Mcewan, T.: Isolation and identification of the toxic principle of Gastrolobium grandiflorum. Nature (Lond.) 201, 827 (1964).

    Article  CAS  Google Scholar 

  • Pattrsox, F. L. M., and R. L. Buchanan: Toxic fluorine compounds. 20. The use of the w-fluorine atom in the study of the metabolism of branched-chain fatty acids. Biochem. J. 92, 100–105 (1964).

    Google Scholar 

  • Peters, R. A., and M. Saorthouse: Fluoride metabolism in plants. Nature (Lond.) 202, 21–22 (1964).

    Article  CAS  Google Scholar 

  • Peters, R. A., M. Shorthouse, and L. R. Murray: Enolase and fluorophosphate. Nature (Lond.) 202, 1331–1332 (1964).

    Article  CAS  Google Scholar 

  • Ward, P. F. V., R. J. Hall, and R. A. Peters: Fluoro-fatty acids in the seeds of Dichapetalum toxicarium. Nature (Lond.) 201, 611–612 (1964).

    Article  CAS  Google Scholar 

  • Williamson, J. R., E. A. Jones, and G. F. Azzone: Metabolic control in perfused rat heart during fluoroacetate poisoning. Biochem. Biophys. Research Comm. 17, 696–702 (1964).

    Article  CAS  Google Scholar 

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Authors
  1. F. L. M. Pattison
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  2. R. A. Peters
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  1. Rochester, N. Y., USA

    Frank A. Smith

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Pattison, F.L.M., Peters, R.A. (1966). Monofluoro Aliphatic Compounds. In: Smith, F.A. (eds) Pharmacology of fluorides. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology, vol 20. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-25198-0_8

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