Abstract
The bioconversions of nitriles and primary amides have a practical interest for the production of optically active α-hydroxy — or α-amino acids and for the preparation of highly pure amides and acids. The appropriate chemical hydrolyses are generally not suitable for such syntheses.
The literature concerning the reactions of nitrile catabolism by living organisms is analyzed. Among these reactions, only hydrolyses are involved in industrial processes.
A large number of economically important products may be obtained by hydrolyzing nitriles or primary amides: acrylamide, lysergic acid, dl- or l-lactic acid, dl - or l-alanien, dl- or l-methionine, dl- or l-phenylalanine, and d- or l-phenylglycine, to name a few. The descriptions of the principal known processes and the possibilities for their improvement are presented and discussed.
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References
Aszalos, A. et al.: J. Antibiot. (Tokyo) Ser. A 19, 285 (1966)
Kikuchi, M.: J. Antibiot. (Tokyo) Ser. A 8, 145 (1955)
Umezawa, H. et al.: Jpn. Patent 10, 245 (1964)
Yamamoto, H. et al.: Ann. Rep. Takeda Res. Lab. 16, 28 (1957)
Seigler, D.S.: Phytochemistry 14, 9 (1975)
Eyjolfson, R.: Fortschr. Chem. Org. Naturst. 28, 74 (1970)
Tapper, B.A., Mac Donald, M.A.: Can. J. Microbiol. 20, 563 (1974)
Strobel, G.A.: J. Biol. Chem. 241, 2618 (1966)
Strobel, G.A.: J. Biol. Chem. 242, 3265 (1967)
Mundy, B.P., Liu, F.H.S., Strobel, G.A.: Can. J. Biochem. 51, 1440 (1973)
Anchel, M.: J. Am. Chem. Soc. 74, 1588 (1952)
Anchel, M.: Trans. N.Y. Acad. Sci. 16, 337 (1954)
Anchel, M.: Science 121, 607 (1955)
Thaller, V., Turner, J.L.: J. Chem. Soc. I, 2032 (1972)
Bohlmann, F., Arndt, C., Stanick, J.: Tetrahedron Lett. 24, 1605 (1963)
Gasco, A. et al.: Tetrahedron Lett. 38, 3431 (1974)
Bianco, M.A., Ceruti Scurti, J.: Allionia 18, 79 (1972)
Ballester, A., Verwey, A., Overeem, J.C.: Phytochemistry 14, 1667 (1975)
Van der Wal, B. et al.: Rec. Trav. Chim. Pays-Bas 87, 238 (1968)
Hofmann, A.W.: Berichte 7, 518 (1874)
Hofmann, A.W.: Berichte 7, 1293 (1874)
Gadamer, J.: Berichte 32, 2336 (1899)
Sabetay, S., Palfray, L., Trabaud, L.: C. R. Acad. Sci. Paris 207, 540 (1938)
Nitsch, J.P., Nitsch, C.: Plant. Physiol. 30, 55 (1955)
Jones, E.R.H. et al.: Nature 169, 485 (1952)
Henbest, H.B., Jones, E.R.H., Smith, G.F.: J. Chem. Soc. 75, 3796 (1953)
Denffer, D.V., Behrens, M., Fischer, A.: Naturwissenschaften 39, 550 (1952)
Bennett-Clark, T.A., Kefford, N.P.: Nature 171, 645 (1953)
Kutacek, V., Kefeli, V.I.: In: Biochemistry and physiology of plant growth substances. Wigtman, F., Setterfield, G. (eds.), p. 127. Ottawa: The Ring Press Ltd 1968
Marion, L.: In: The alcaloids: chemistry anbd physiology, Vol. 1, p. 206. New York: Academic Press 1950
Mukherjee, R., Chatterjee, A.: Chem. Ind., 1524 (1964)
Mukherjee, R., Chatterjee, A.: Tetrahedron 22, 1461 (1966)
Bell, E.A.: In: Chemotaxonomy of the leguminosae. Harbone, J.B., Boulter, D., Turner, B.L. (eds.), p. 179. London, New York: Academic Press 1971
Schilling, E.D., Strong, F.M.: J. Am. Chem. Soc. 77, 2843 (1955)
Tschiersch, B.: Pharmazie 21, 445 (1966)
Schilling, E.D., Strong, F.M.: J. Am. Chem. Soc. 76, 2848 (1954)
Van Rompuy, L. et al.: Biochem. Biophys. Res. Commun. 56, 199 (1974)
Mikolajczack, K.L.: Prog. Chem. 15, 97 (1977)
Seigler, D.S.: Biochem. Syst. Ecol. 4, 235 (1976)
Gowrikumar, G., Mani, V.V.S., Lakshminarayana, G.: Phytochemistry 15, 1566 (1976)
Pallares, E.S.: Arch. Biochem. 9, 105 (1946)
Moore, B.P.: J. Aust. Entomol. Soc. 6, 36 (1967)
Blum, M.S., Woodring, J.P.: Science 138, 512 (1962)
Jones, D.A., Parson, J., Rothschild, M.: Nature 193, 52 (1962)
Barbetta, M., Casnati, G., Pavan, M.: Mem. Soc. Entomol. 45, 169 (1966)
Casnati, G. et al.: Experientia 19, 409 (1963)
Eisner, T.: Ann. Rev. Entomol. 7, 107 (1962)
Jacobson, M.: Ann. Rev. Entomol. 11, 403 (1966)
Duffey, S.S., Underhill, E.W., Towers, G.H.N.: Comp. Biochem. Physiol. B 47, 753 (1974)
Eisner, T. et al.: Science 139, 1218 (1963)
Eisner, H.E., Eisner, T., Hurst, J.J.: Chem. Ind. (London) 124 (1963)
Eisner, H.E., Alsop, D.W., Eisner, T.: Psyche 74, 107 (1967)
Eisner, T., Eisner, H.E.: Natural History 74, 30 (1965)
Fulmor, W. et al.: Tetrahedron Lett. 52, 4451 (1970)
Fawcett, C.H. et al.: Proc. Roy. Soc. London B 148, 543 (1958)
Fawcett, C.H. et al.: Nature 176, 1026 (1955)
Taylor, H.F., Wain, R.L.: Nature 184, 1142 (1959)
Chamberlain, K., Wain, R.L.: Ann. Appl. Biol. 75, 409 (1973)
Ohkawa, H. et al.: Pesti. Biochem. Physiol. 2, 95 (1972)
Frankenberg, L., Sorbo, B.: Arch. Toxikol. 31, 99 (1973)
Contessa, A.R., Santi, R.: Biochem. Pharmacol. 22, 827 (1973)
Lang, K.: Biochem. Z. 259, 243 (1933)
Pattison, F.L.M.: Nature 172, 1139 (1953)
Pattison, F.L.M. et al.: J. Am. Chem. Soc. 78, 3484 (1956)
Kjaer, A., Lansen, P.O.: Biosynthesis 2, 171 (1973)
Kjaer, A., Lansen, P.O.: Biosynthesis 4, 179 (1976)
Conn, E.E.: Biochem. Soc. Symp. 38, 277 (1974)
Schutte, H.R.: In: Fortschritte der Botanik, Vol. 35, p. 103. Berlin: Springer Verlag 1973
Hughes, M.A., Conn, E.E.: Phytochemistry 15, 697 (1976)
Knowles, C.J.: Bacteriol. Rev. 40, 652 (1976)
Gewitz, H.S. et al.: Planta 131, 149 (1976)
Seely, M.K., Criddle, R.S., Conn, E.E.: J. Biol. Chem. 241, 4457 (1966)
Mao, C.H., Anderson, L.: Phytochemistry 6, 473 (1967)
Burckhardt, H., Kleinschmidt, T.: Z. Physiol. Chem. 348, 753 (1967)
Kleinschmidt, T., Glossmann, H., Horst, J.: Z. Physiol. Chem. 351, 349 (1970)
Colotelo, N., Ward, E.W.B.: Nature 189, 242 (1961)
Bove, C., Conn, E.E.: J. Biol. Chem. 236, 207 (1961)
Stevens, D.L., Strobel, G.A.: J. Bacteriol. 95, 1094 (1968)
Haisman, D.R., Knight, D.J.: Biochem. J. 103, 528 (1967)
Diericks, P., Wauters, E., Vendrig, J.: Z. Pflanzenphysiol. 75, 191 (1975)
Butler, G.W., Bailey, R.W., Kennedy, L.D.: Phytochemistry 4, 369 (1965)
Hardy, R.W.F., Burns, R.C., Pashall, G.W.: In: Inorganic biochemistry, Vol. 2, Chap. 23, p. 745. Eichkorn, G. (ed.). Amsterdam: Elsevier 1973
Postgate, J.R.: The chemistry and biochemistry of nitrogen fixation. London: Plenum Press 1971
Schrauzer, G.N. et al.: J. Am. Chem. Soc. 94, 7378 (1972)
Fuchsman, W.H., Hardy, R.W.F.: Bioinorg. Chem. 1, 197 (1971)
Vincent, C., Delachenal, C.: C. R. Acad. Sci. Paris 86, 340 (1879)
Ressler, C., Redstone, P.A., Erenberg, R.H.: Science 134, 188 (1961)
Uematsu, T., Suhadolnik, R.J.: Arch. Biochem. Biophys. 162, 614 (1974)
Theriault, R.J., Longfield, T.H., Zaugg, H.E.: Biochemistry 11, 385 (1972)
Fowden, L., Bell, E.A.: Nature 206, 110 (1965)
Castric, P.A., Conn, E.E.: J. Bacteriol. 108, 132 (1971)
Castric, P.A., Farnden, K.J.F., Conn, E.E.: Arch. Biochem. Biophys. 152, 62 (1972)
Thimann, K.V., Mahadevan, S.: Nature 181, 1466 (1958)
Thimann, K.V., Mahadevan, S.: Arch. Biochem. Biophys. 105, 133 (1964)
Mahadevan, S., Thimann, K.V.: Arch. Biochem. Biophys. 107, 62 (1964)
Harper, D.B.: Biochem. Soc. Trans. 4, 502 (1976)
Harper, D.B.: Biochem. J. 165, 309 (1977)
Harper, D.B.: Biochem. J. 167, 685 (1977)
Mimura, A., Kawano, T., Yamaga, K.: J. Ferment. Technol. 47, 631 (1969)
Grant, D.J.W.: Antonie van Leeuwenhoek 39, 273 (1973)
Firmin, J.L., Gray, D.O.: Biochem. J. 158, 223 (1976)
Di Geronimo, M.J., Antoine, A.D.: Appl. Environm. Microbiol. 31, 900 (1976)
Robinson, W.G., Hook, R.H.: J. Biol. Chem. 239, 4257 (1964)
Hook, R.H., Robinson, W.G.: J. Biol. Chem. 239, 4263 (1964)
Pate, D.A., Funderburk, H.: Proz. Symp. Lise Isotopes Weed. Res. 12, 17 (1965)
Fournier, J.C.: Chemosphere 3, 77 (1974)
Smith, A.E., Cullimore, D.R.: Can. J. Microbiol. 20, 773 (1974)
Fukuda, Y. et al.: J. Ferment. Technol. 49, 1011 (1971)
Farnden, K.J.F.: Ph. D. Thesis, University of Adelaide (1970)
Lauinger, C., Ressler, C.: Biochem. Biophys. Acta 198, 316 (1970)
Jackson, R.C., Handschumacher, R.E.: Biochemistry 9, 3585 (1970)
Giza, Y.H., Ratzkin, H., Ressler, C.: Fed. Proc. 22, 651 (1963)
Stowe, B.B., Thimann, K.V.: Arch. Biochem. Biophys. 51, 499 (1954)
Seeley, R.C. et al.: Chemistry and mode of action of plant growth substances. London: Butterworths Scientific Publications 1956
Roberts, T.R., Standen, M.E.: Pestic. Sci. 8, 600 (1977)
Williams, R.T.: In Detoxication mechanisms. New York: John Wiley and Sons 1959
Bray, H.G., Hybs, Z., Thorpe, W.V.: Biochem. J. 48, 192 (1951)
Ponseti, I.V. et al.: Proc. Soc. Exp. Biol. Med. 93, 515 (1956)
Ludzack, F.J. et al.: Sewage Ind. Wastes 31, 33 (1959)
Arnaud, A., Galzy, P., Jallageas, J.C.: C. R. Acad. Sci. Paris 287, 571 (1976)
Arnaud, A., Galzy, P., Jallageas, J.C.: Rev. Ferment. Ind. Aliment. 31, 39 (1976)
Marvel, C.S., Brubaker, M.M.: Organic syntheses, Vol. 1. New York: John Wiley and Sons Inc. 1948
Bejaud, M. et al.: Tetrahedron 31, 403 (1975)
Du Preez, J.C., Lategan, P.M.: J. Chromatogr. 124, 63 (1976)
Bruce, R.B., Howard, J.W., Hanzal, R.F.: Anal. Chem. 27, 1346 (1955)
Jallageas, J.C., Arnaud, A., Galzy, P.: Anal. Biochem. 95, 436 (1979)
Jallageas, J.C., Arnaud, A., Galzy, P.: J. Chromatogr. 166, 181 (1978)
Arnaud, A., Galzy, P., Jallageas, J.C.: Agric. Biol. Chem. 41, 2183 (1977)
Becke, F., Fleig, H., Paessler, P.: Liebigs Ann. Chem. 749, 198 (1971)
Wineman, R.J., Eu-Phang T. Hsu, Anagnostopoulos, C.E.: J. Am. Chem. Soc. 80, 6233 (1958)
Francis, W.C. et al.: J. Am. Chem. Soc. 80, 6238 (1958)
Arnaud, A., Galzy, P., Jallageas, J.C.: Folia Microbiol. 21, 178 (1976)
Jallageas, J.C., Arnaud, A., Galzy, P.: J. Gen. Microbiol. 24, 103 (1978)
Jakoby, W.B., Fredericks, J.: J. Biol. Chem. 239, 1978 (1964)
Thalenfeld, B., Grossowicz, N.: J. Gen. Microbiol. 94, 131 (1976)
Clarke, P.H., Tata, R.: J. Gen. Microbiol. 75, 231 (1973)
Arnaud, A. et al.: CNRS — ANVAR Fr. 73,33613 (19 Décembre 1973)
Galzy, P. et al.: CNRS — ANVAR Fr. 74,41828 (18 Décembre 1974)
Jallageas, J.C., Arnaud, A., Galzy, P.: CNRS — ANVAR Fr. 7901803 (24 Janvier 1979)
Societa Farmaceutici Italia: Belg. Pat. 634, 836 (January 13, 1964)
Kawaken Fine Chemicals Company: Jap. Pat. 9042886 (September 3, 1972)
Stamicarbon, B.V.: Lux. Pat. 74,142 (8 Janvier 1976)
Stamicarbon, B.V.: Pays-Bas Pat. 75,14301 (9 Décembre 1975)
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Jallageas, JC., Arnaud, A., Galzy, P. (1980). Bioconversions of nitriles and their applications. In: Advances in Biochemical Engineering, Volume 14. Advances in Biochemical Engineering, vol 14. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0007187
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DOI: https://doi.org/10.1007/BFb0007187
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