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.
Keywords
- Citric Acid Cycle
- Hydrogen Fluoride
- Nicotinamide Adenine Dinucleotide Phosphate
- Fluorine Compound
- Kidney Mitochondrion
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Aldous, J. G., and K. R. Rozee: The effect of pH on the toxicity of fluoroacetic acid. Biochem. J. 62, 605–610 (1956).
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).
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).
Annison, E. F., K. J. Hill, D. B. Lindsay, and R. A. Peters: Fluoroacetate poisoning in sheep. J. comp. Path. 70, 145–155 (1960).
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).
Avi-Don, Y., and J. Mager: The effect of fluoropyruvate on the respiration of animal-tissue preparations. Biochem J. 63, 613–618 (1956a).
Avi-Don, Y., and J. Mager: A spectrophotometric method for determination of cysteine and related compounds. J. biol. Chem. 222, 249–258 (1956b).
Bacq, Z. M., and P. A. Alexander: Fundamentals of radiobiology, 555pp., 2nd Ed. Oxford: — Pergamon Press 1961.
S. Bliéecq-Hutter, and C. Liébecq: Protection against irradiation afforded by sodium fluoroacetate. Radiat. Res. 13, 286–297 (1960).
Badeniiuizen, N. P., and J. Slinger: Detection of monofluoroacetic acid in Gifblaar. (Dichapetalum cymosum (Hook) Engl) S Afr. J. Sci. 50, 269–270 (1954).
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.
Bartlett, G. R.: Mechanism of action of 2-fluoroethanol. J. Pharmacol. exp. Ther. 106, 464–467 (1952).
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).
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).
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).
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.
Bergmann, E. D., and S. Cohen: Organic fluorine compounds. Fluorine derivatives of mevalolactone. Tetrahedron Letters, No. 8, 20–22 (1960).
Bergmann, E. D., and S. Cohen: Organic fluorine compounds. Part Xxii. Fluorine analogues of mevalonic acid. J. chem. Soc. 1961 a, 3457–3460.
Bergmann, E. D., and S. Cohen: Organic fluorine compounds. Part Xxvi. Synthesis of a-fluoro-ß-alanine. J. chem. Soc. 1961 b, 4669–4671.
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.
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.
Bergmann, E. D., and R. Ikan: The reaction of diazoketones with anhydrous hydrofluoric acid. Chem. and Ind. ( London ) 1957, 394.
Bergmann, E. D., and I. Shahax: Transformation of toluene-p-sulphonates into fluorides. Chem. and Ind. ( London ) 1958, 157.
Bergmann, E. D., and I. Shahax: Triethyl a-fluoroaconitate. Nature (Lond.) 185, 529–530 (1960).
Bergmann, E. D., and I. Shahax: A simple preparation of fluoromalonic acid esters. Chem. and Ind. ( London ) 1961, 591.
Black, S., and J. O. Hutchens: The oxidation of acetate by yeast in the presence of fluoro-acetate. Arch. Biochem. 17, 211–223 (1948).
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.
Blohm, T. R.: Fluoroacetylcholine bromide and some other choline ester salts. J. Amer. chem. Soc. 73, 5445–5446 (1951).
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).
Bowers, A.: Steroids. Cxxix. A new general route to fluorinated steroids. J. Amer. chem. Soc. 81, 4107–4108 (1959).
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).
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).
Brady, R. O.: Fluoroacetyl coenzyme A. J. biol. Chem. 217, 213–224 (1955).
Brady, R. O.: Enzymic synthesis of fatty acids by aldol condensation. Proc. Nat. Acad. Sci. (Wash.) 44, 993–998 (1958).
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).
Brown, P. J., and B. C. Saunders: A new synthesis of monofluorocitric acid. Chem. and Ind. ( London ) 1962, 307–308.
Buchanan, J. M., and C. B. Anfinsen: Partial purification of aconitase. J. biol. Chem. 180, 47–54 (1949).
Buchanan, R. L., F. H. Dean, and F. L. M. Pattison: y-Fluoroglutamic acid. Canad. J. Chem. 40, 1571–1575 (1962a).
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).
Buchanan, R. L., and F. L. M. Pattison: Unpublished results (1962).
Buchanan, R. L., and F. L. M. Pattison: Unpublished results (1963).
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.
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).
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).
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).
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).
Bulen, W. A., J. E. Varner, and R. C. Burrell: Separation of organic acids from plant tissues. Anal. Chem. 24, 187–190 (1952).
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).
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).
Callely, A. G., and S. Dagley: A possible lethal synthesis of monofluoromalonate. Biochem. biophys. Acta (Amst) 35, 256–257 (1959).
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).
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.
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.
Chari-Bitron, A.: A study on the toxicity and the biochemical effects of monofluoromalonate. Biochem. Pharmacol. 6, 169–176 (1961).
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).
Chenoweth, M. B.: Monofluoroacetic acid and related compounds. Pharmacol. Rev. 1, 383–424 (1949).
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).
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).
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).
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).
Cole, B. T., F. L. Engel, and K. Hewson: Some metabolic effects of sodium fluoracetate poisoning in the rat. Fed. Proc. 13, 28 (1954).
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).
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).
Dawson, R. M. C.: Cerebral amino acids in fluoroacetate poisoned, anaesthetised and hypoglycaemic rats. Biochim. biophys. Acta (Amst) 11, 548–552 (1953).
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).
Dawson, R. M. C., and D. Richter: Effects of stimulation on the phosphate esters of the brain. Amer. J. Physiol. 160, 203–211 (1949).
Dean, F. H., and F. L. M. Pattison: Unpublished results (1962).
Dean, F. H., and F. L. M. Pattison: Monofluorosuccinic acid. Canad. J. Chem. 41, 1833–1836 (1963).
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).
Dickman, S. R., and A. A. Cloutier: Factors affecting the activity of aconitase. J. biol. Chem. 188, 379–388 (1951).
Dixon, G. H., H. L. Kornberg, and P. Lund: Purification and properties of malate synthetase. Biochim. biophys. Acta (Amst.) 41, 217–233 (1960).
Dixon, M.: Biochem. Soc. Symposia. No. 2. p. 42. On the Biochemical Reactions of Chemical Warfare Agents. Cambridge Univ. Press (1948).
Dixon, M., and D. M. Needham: Biochemical research on chemical warfare agents. Nature (Lond.) 158, 432–438 (1946).
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).
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).
Elliott, W. B., and G. Kalnitsky: A mechanism for fluoroacetate inhibition. J. biol. Chem. 186, 487–493 (1950).
Elliott, W. B., and A. Marcus: Enzymatic reactions of fluoroacetyl phosphate. J. biol. Chem. 234, 1011–1014 (1959);
Elliott, W. B., and A. Marcus: Enzymatic reactions of fluoroacetyl phosphate. Fed. Proc. 14, 201 (1955).
Elliott, W. B., and A. Marcus: Fluoroacetyl phosphate, preparation and properties. J. Amer. chem. Soc. 80, 4287 (1958).
Elliott, W. B., and A. H. Phillips: Effect of fluoroacetate on glucose metabolism in vivo. Archiv. Biochem. 49, 389–395 (1954).
Elsden, S. R., and J. G. Ormerod: The effect of monofluoroacetate on the metabolism of Rhodospirillum rubrum. Biochem. J. 63, 691–701 (1956).
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).
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).
Fanshier, D. W., L. K. Gottwald, and E. KuN: Enzymic synthesis of monofluorocitrate from ß-fluoro-oxaloacetate. J. biol. Chem. 237, 3588–3596 (1962).
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).
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).
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).
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).
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).
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).
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).
Fraser, R. R., and F. L. M. Pattison: Ethyl co-fluoroacetoacetate. Nature (Lond.) 176, 696 (1955).
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).
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).
Gal, E. M.: Studies of enzyme inhibition by fluoromalate and fluoroacetoacetates. Arch. Biochem. 90, 278–287 (1960).
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).
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).
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).
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.
Gitter, S.: The influence of acetamide on citrate accumulation after fluoroacetate poisoning Biochem. J. 63, 182–187 (1956).
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).
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).
Gordon, R. S., and A. Cherkes: Unesterified fatty acid in human blood plasma. J. clin. Invest. 35, 206–212 (1956).
Gotto, A. M., and H. L. Kornberg: Properties of a glycerate-forming enzyme from Pesudomonas ovalis (Chester). Biochem. J. 79, 9 P (1961).
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.
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).
Hall, R. J.: The determination of microgram amounts of fluorine by diffusion. Analyst. 85, 560–563 (1960).
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).
Hall, R. J., and P. F. V. Ward: Unpublished results (1962).
Hartman, K.-U., and C. Heidelberger: Studies on fluorinated pyrimidines. Xiii. Inhibition of thymidylate synthetase. J. biol. Chem. 236, 3006–3013 (1961).
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).
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).
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).
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).
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).
Hoffmann, F. W.: Preparation of aliphatic fluorides. J. Amer. chem. Soc. 70, 2596–2597 (1948).
Hoffmann, F. W.: Aliphatic fluorides. I. w,w’-Difluoroalkanes. J. Org. Chem. 14, 105–110 (1949).
Hoffmann, F. W.: Aliphatic fluorides. II. 1-Halogeno-w-fluoroalkanes. J. Org. Chem. 15, 425–434 (1950).
Horiuchi, N.: C—F bond rupture in monofluoroacetate. Seikagaku 34, 92–98 (1962 a). [J. Jap. Biochem. Soc., in Japanese.]
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.]
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).
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).
Hudlicki, M.: Organic compounds of fluorine. II. Fluorinated amino acids. Coll. Czech. Chem. Comm. 26, 1414–1421 (1961).
Hudlicki, M.: Chemistry of Organic Fluorine Compounds. New York: MacMillan 1962.
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.
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).
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).
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).
Jarrett, J. G., and A. Packham: Response of the sheep to sublethal doses of fluoroacetate. Nature (Lond.) 177, 580–581 (1956).
Jayasuriya, G. C. N.: Citrate accumulation from glycollate by an oxalate-decomposing organism Biochem. J. 56, xli (1954);
Jayasuriya, G. C. N.: Citrate accumulation from glycollate by an oxalate-decomposing organism Biochem. J. 58, xxxi (1954).
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).
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).
Judah, J. D., and K. R. Rees: Activation of fatty acid oxidation by kidney and liver mitochondria. Biochem. J. 55, 664–668 (1953).
Judah, J. D., and K. R. Rees: A note on the action of fluoroacetate. Biochem. J. 57, 374–376 (1954).
Kacser, H.: The stereochemical relations of the four fluorocitrate isomers. Disc. Faraday Soc. 20, 283–286 (1955).
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).
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).
Kandel, A., and M. B. Crenoweth: Tolerance to fluoroacetate and fluorobutyrate in rats. J. Pharmacol. exp. Ther. 104, 248–252 (1952b).
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.
Kilby, B. A., and K. J. Carpenter: Unpublished report (1944).
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).
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].
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].
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.].
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).
Kochmann, M.: Inhalation anesthesia. In Heffter’S Handbuch der exp. Pharm. 1, 133–261 (1923).
Kornberg, H. L., and S. R. Elsden: The metabolism of 2-carbon compounds by microorganisms. Advanc. Enzymol. 23, 401–470 (1961).
Krasna, A. I.: The inhibition of fumarase and malic dehydrogenase by DL-ß-fluoromalic acid. J. biol. Chem. 236, 749–753 (1961).
Krasna, A. I.: The stereochemical configuration of ni,-ß-fluoromalic acid. J. biol. Chem. 237, 1418–1420 (1962).
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).
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).
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).
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).
Lang, S.: Über die Umwandlung des Acetonitrils und seiner Homologen im Thierkörper. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 34, 247–258 (1894).
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).
LiebÉCQ, C., and R. A. Peters: The toxicity of fluoroacetate and the tricarboxylic acid cycle. Biochim. biophys. Acta (Amst) 3, 215–230 (1949).
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).
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).
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).
Mager, J., and I. Blank: Synthesis of fluoropyruvic acid and some of its biological properties. Nature (Lond.) 173, 126 (1954).
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).
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).
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).
Marcus, A., and W. B. Elliott: Enzymatic reactions of fluoroacetate and fluoroacetyl coenzyme A. J. biol. Chem. 218, 823–830 (1956).
Marcus, A., and W. B. Elliott: Fluoroacetyl phosphate; preparation and properties. J. Amer. chem. Soc. 80, 4287–4291 (1958).
Martius, C.: Über den Abbau der Citronensäure. Z. physiol. Chem. 247, 104–110 (1937).
Martius, C.: Der intermediare Stoffwechsel der Citronensäure. Z. physiol. Chem. 257, 29–42 (1938).
Martius, C.: Über die Unterbrechung des Citronensäure-Cyklus durch Fluoressigsäure. Ann. 561, 227–232 (1949).
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).
Meuler, A H, and Y. T. Chang: Biological reactions of fluoroacetyl choline. Arch. Biochem. 62, 293–298 (1956).
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).
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).
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).
Millington, J. E., and F. L. M. Pattison: Toxic fluorine compounds. Xii. Esters of w-fluoroalcohols. Canad. J. Chem. 34, 1532–1541 (1956).
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).
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).
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).
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).
Morrison, J. F.: The purification of aconitase. Biochem. J. 56, 99–105 (1954).
Miura, K., and R. A. Peters: Biochemistry of fluoroacetate poisoning: the effect of fluorocitrate on purified aconitase. Biochem. J. 58, 473–479 (1954).
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).
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).
Nair, P. V., and H. Busch: Improved synthesis of monofluoro-and monochloropyruvic acids. J. org. Chem. 23, 137–139 (1958).
Newman, M. S., M. W. Renoll, and I. Auerbach: Synthesis and reduction of difluorodecanoic acid derivatives. J. Amer. chem. Soc. 70, 1023–1024 (1948).
Newton, J., and F. L. M. Pattison: Unpublished results, 1961.
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).
O’Brien, R. D., and R. A. Peters: The metabolism of DL-1-deoxy-1-fluoroglycerol. Biochem. J. 79, 188–195 (1958b).
Oelrichs, P. B., and T. Mcewan: Isolation of the toxic principle in Acacia georginae. Nature (Lond.) 190, 808–809 (1961).
Oelrichs, P. B., and T. McEwan: The toxic principle of Acacia georginae. Queensland J. Agric. Sci. 19, 1–16 (1962).
Olaa, G. A.: Unpublished results, cited in: G. A. Olah, Ed. Friedel-Crafts and related reactions, Vol. I, 40. New York: Interscience Publishers 1963.
Olah, G., u. S. Kuhn: Darstellung und Untersuchung organischer Fluorverbindungen. Xxi Darstellung von Fluoracetaldehyd und aliphatischen Fluormethylketonen. Chem. Ber. 89, 864–865 (1956).
Oliveira, M. M.: Chromatographic isolation of monofluoroacetic acid from Palicourea marcgravii St. Hil. Experientia 19, 586–587 (1963).
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).
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).
Parker, J. M., and I. G. Walker: A toxicological and biochemical study of co-fluoro compounds. Canad. J. Biochem. 35, 407–417 (1957).
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.
Pattison, F. L. M.: Toxic fluorine compounds. I. Nature (Lond.) 172, 1139–1141 (1953).
Pattison, F. L. M.: Toxic fluorine compounds. II. Nature (Lond.) 174, 737–741 (1954).
Pattison, F. L. M.: From war to peace: toxic aliphatic fluorine compounds. Chem. Canada 9, 27–33 (1957).
Pattison, F. L. M.: Toxic Aliphatic Fluorine Compounds. Amsterdam: Elsevier 1959.
Pattison, F. L. M.: Unpublished results, 1962.
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).
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).
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).
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).
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).
Pattison, F. L. M., and W. C. Howell: Toxic fluorine compounds. IV. co-Fluoroalkyl halides. J. org. Chem. 21, 748–753 (1956a).
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).
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).
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).
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).
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).
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).
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).
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.
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).
Pattison, F. L. M., and R. G. Woolford: (+)-18-Fluoro-l0-methyloctadecanoic acid (Fluorotuberculostearic acid). J. Amer. chem. Soc. 79, 2306–2308 (1957a).
Pattison, F. L. M., and R. G. Woolford: Toxic fluorine compounds. Xvi. Branched w-fluorocarboxylic acids. J. Amer. chem. Soc. 79, 2308–2311 (1957b).
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).
Peeters, G., R. Coussens, and G. Sierins: Sodium monofluoroacetate and the isolated lactating cow udder. Arch. int. Pharmacodyn. 98, 288–301 (1954).
Peters, R. A.: Lethal synthesis. [Croonian lecture.] Proc. roy. Soc. B, 139, 143–170 (1952).
Peters, R. A.: Dohme Lectures. Biochemistry of some toxic agents. Bull. Johns Hop. Hosp. 97, 1–42 (1955).
Peters, R. A.: Mechanism of the toxicity of the active constituent of Dichapetalum cymosum and related compounds. Advanc. Enzymol. 18, 113–159 (1957).
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).
Peters, R. A.: Further experiments on the inhibition of aconitase by enzymically prepared fluorocitric acid. Biochem. J. 79, 261–268 (1961).
Peters, R. A.: Biochemical lesions and lethal synthesis, pp. 1–132 (p. 113 ). Oxford: Pergamon Press 1963.
Peters, R. A.: Applications of chemical defence research in medicine. Edinb. med. J. 48, 197–213 (1951).
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).
Peters, R. A., and R. J. Hall: Further observations upon the toxic principle of Dichapetalum toxicarium. Biochem. Pharmacol. 2, 25–36 (1959).
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).
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.
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).
Peters, R. A., and M. Shorthouse: Unpublished results, 1962.
Peters, R. A., and R. W. Wakelin: Pyruvate oxidate system in brain tissue. J. Physiol. (Lond.) 119, 421–427 (1953).
Peters, R. A., and R. W. Wakelin: Synthesis of fluorocitric acid and its inhibition in acetate. Biochem. J. 67, 280–286 (1957).
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);
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).
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).
Peters, R. A., R. W. Wakelin, and A. B. Hastings: Proc. xix. Inter. Congress of Physiology. p. 674 (1953).
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).
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).
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).
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).
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).
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).
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).
Raasch, M. S.: 5-Fluoronorvaline and 6-fluoronorleucine. J. org. Chem. 23, 1567–1568 (1958).
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).
Renner, W.: A case of poisoning by the fruit of Chailletia toxicaria (ratsbane). Brit. med. J. 1904 I, 1314.
Rimington, C.: Chemical investigation of the Gifblaar, Dichapetalum cymosum (Hook) Engl. 1. Onderstepoort J. Vet. Sci. Animal Indust. 5, 81 (1935).
Rivett, D. E. A.: The synthesis of monofluorocitric acid. J. chem. Soc. 1953, 3710–3711.
Rose, I. A., M. Greenberg-Manago, S. R. Korey, and S. OcHoA: Enzymatic phosphorylation of acetate. J. biol. Chem. 211, 737–756 (1954).
Rothstein, A.: Symposia Soc. Exp. Biol. No. viii, pp. 165–201. Cambridge: Univ. Press 1954.
Saunders, B. C.: Toxic properties of w-fluoro-carboxylic acids and derivatives. Nature (Lond.) 160, 179–181 (1947).
Saunders, B. C.: Phosphorus and fluorine, p. 212. Cambridge: Univ. Press 1957.
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.
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.
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.
Salle, J.: Sur les propriétés du bromure de fluoroacétylcholine (F.Ach). Arch. int. Pharmacodyn. 91, 339–349 (1952).
Schmidt, G., u. H. Jahn: Synthese der a-Fluor-mevalonsäure. Ann. 644, 43–47 (1961).
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).
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).
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).
Stoner, H. B.: The mechanism of toxic hepatic necrosis. Brit. J. exp. Path. 37, 176–198 (1956).
Swarts, F.: Sur l’acide fluoroacétique. Bull. Acad. roy. Belg. [3] 31, 675–688 (1896).
Taylor, N. F., and P. W. Kent: Synthesis of (+) methyl fluoromalate. Nature (Lond.) 174, 401 (1954).
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.
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.
Taylor, T. G.: A modified procedure for the microdetermination of citric acid. Biochem. J. 54, 48–49 (1953).
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).
Theiler, A.: Quoted by Steyn, D. G. 1928 (q.v.) (1902).
Tourtellotte, W. W., and J. M. Coon: Treatment of fluoroacetate poisoning in mice and dogs. J. Pharmacol. exp. Ther. 101, 82–91 (1951).
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).
Treble, D. H.: The metabolism of 2-fluoroethanol. Biochem. J. 82, 129–134 (1962).
Treble, D. H., and R. A. Peters: The metabolism of 2-deoxy-2-fluoroglyceraldehyde. Biochem. J. 80, 15–16 P (1961).
Treble, D. H., and R. A. Peters: Metabolism of 2-deoxy-2-fluoroglyceraldehyde. Biochem. Pharmacol. 11, 891–899 (1962).
Tschesche, R., u. H. Machleidt: Synthesen von substituierten ß-Hydroxy-ß-methyl-glutarsäuren und Mevalonsäuren. Ann 631, 61–76 (1960).
Tullock, C. W., and D. D. Coffman: Synthesis of fluorides by metathesis with sodium fluoride. J. org. Chem. 25, 2016–2019 (1960).
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).
Walker, I. G., and J. M. Parker: Further toxicological and biochemical studies on co-fluoro compounds. Canad. J. Biochem. 36, 339–345 (1958).
Ward, P. F. V., and R. A. Peters: The chemical and biochemical properties of fluorocitric acid. Biochem. J. 78, 661–668 (1961).
Weeks, J R, and M. B. Chenoweth: Separation by fluoroacetate of energy sources for smooth muscle contraction. Fed. Proc. 8, 345 (1949).
Whittem, J. H.: Communication with L. R. Murray to Austral. Vet. Assoc. Annual Conf., May 1963.
Wilshire, J. F. K., and F. L. M. Pattison: Toxic fluorine compounds. XI. w-Fluoroaldehydes. J. Amer. chem. Soc. 78, 4996–4998 (1956).
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).
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].
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).
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).
Buchanan, R. L., and F. L. M. Pattrsox: Preparation of a-fluoro-y-aminoacids. Canad. J. Chem. 43, 3466–3468 (1965).
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).
Lahiri, S, and J. H. Quastel: Fluoroacetate and the metabolism of ammonia in the brain. Biochem. J. 89, 157–163 (1963).
Mcewan, T.: Isolation and identification of the toxic principle of Gastrolobium grandiflorum. Nature (Lond.) 201, 827 (1964).
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).
Peters, R. A., and M. Saorthouse: Fluoride metabolism in plants. Nature (Lond.) 202, 21–22 (1964).
Peters, R. A., M. Shorthouse, and L. R. Murray: Enolase and fluorophosphate. Nature (Lond.) 202, 1331–1332 (1964).
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).
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).
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1966 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
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
Download citation
DOI: https://doi.org/10.1007/978-3-662-25198-0_8
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-23198-2
Online ISBN: 978-3-662-25198-0
eBook Packages: Springer Book Archive