Archives of Microbiology

, Volume 110, Issue 1, pp 87–90 | Cite as

The bacterial oxidation of nicotinic acid

N-Formylmaleamic and N-formylfumaramic acids
  • E. J. Behrman


N-Formylmaleamic acid, a probable intermediate in the bacterial metabolism of nicotinic acid, has been synthesized by photoisomerization of its transisomer, N-formylfumaramic acid. The compound previously reported to be N-formylmaleamic acid has been shown to be N-formylfumaramic acid.

Key words

Nicotinic acid N-Formylmaleamic acid N-Formylfumaramic acid Pseudomonas 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Aldersley, M. F., Kirby, A.J., Lancaster, P. W., McDonald, R. S., Smith, C. R.: Intramolecular catalysis of amide hydrolysis by the carboxy-group. J. chem. Soc. Perkin II, 1487–1495 (1974)Google Scholar
  2. Anschütz, R.: Über die Amin- und Anilsäuren der Fumarsäure und der Maleinsäure. Justus Liebigs Ann. Chem. 259, 137–148 (1890)Google Scholar
  3. Bachstez, M., Cavallini, G.: Über Hydro-Orotsäure Chem. Ber. 66, 681–683 (1933)Google Scholar
  4. Batt, R. D., Martin, J. K., Ploeser, J. M., Murray, J.: Chemistry of the dihydropyrimidines. Ultraviolet spectra and alkaline decomposition. J. Amer. chem. Soc. 76, 3663–3665 (1954)Google Scholar
  5. Behrman, E. J., Stanier, R. Y.: The bacterial oxidation of nicotinic acid. J. biol. Chem. 228, 923–945 (1957)Google Scholar
  6. Beilsteins Handbuch der organischen Chemie (F. Richter, Hrsg.), 4. Aufl., Bd. 3, S. 133–134. Berlin-Heidelberg-New York: Springer 1961Google Scholar
  7. Brown, J., Su, S. C. K., Shafer, J. A.: The hydrolysis and cyclization of some phthalamic acid derivatives. J. Amer. chem. Soc. 88, 4468–4474 (1966)Google Scholar
  8. Bruylants, A., Kezdy, F.: Recent studies on the hydrolysis of aliphatic amides. Rec. chem. Progr. 21, 213–240 (1960)Google Scholar
  9. Cavallito, C. J., Smith, C. S.: The action of halogens on α,β-un-saturated ureides. J. Amer. chem. Soc. 63, 995–997 (1941)Google Scholar
  10. Dahlgren, G., Simmerman, N. L.: The effect of ethyl substitution on the kinetics of the hydrolysis of maleamic and phthalamic acid. J. phys. Chem. 69, 3626–3630 (1965)Google Scholar
  11. Deghenghi, R.: Über Fumarursäure. Chem. Ber. 90, 255–257 (1957)Google Scholar
  12. Dunlap, F. L., Phelps, I. K.: The action of urea and primary amines on maleic anhydride. Amer. chem. J. 19, 492–496 (1897)Google Scholar
  13. Euranto, E. K.: Esterification and ester hydrolysis, Table 5. In: The chemistry of carboxylic acids and esters (S. Patai, ed.), p. 519, New York: Wiley 1969Google Scholar
  14. Gauthier, J. J., Rittenberg, S. C.: The metabolism of nicotinic acid. I. Purification and properties of 2,5-dihydroxypyridine oxygenase from Pseudomonas putida N-9. J. biol. Chem. 246, 3737–3742 (1971a)Google Scholar
  15. Gauthier, J. J., Rittenberg, S. C.: The metabolism of nicotinic acid. II. 2,5-Dihydroxypyridine oxidation, product formation, and oxygen-18 incorporation. J. biol. Chem. 246, 3743–3748 (1971b)Google Scholar
  16. Glasoe, P. K., Long, F. A.: Use of glass electrodes to measure acidities in deuterium oxide. J. phys. Chem. 64, 188–190 (1960)Google Scholar
  17. Griess, P.: Über die Einwirkung von Jodmethyl auf Asparagin. Chem. Ber. 12, 2117–2119 (1879)Google Scholar
  18. Kirby, A. J., Fersht, A. R.: Intramolecular catalysis. Prog. Bioorg. Chem. 1, 1–82 (1971)Google Scholar
  19. Mackenzie, K.: Acid-base catalysis in the stereomutation of ethylenic carbonyl compounds. In: The chemistry of alkanes (S. Patai, ed.), pp. 397–399. New York: Wiley 1964Google Scholar
  20. Michael, A., Wing, J. F.: On the action of methyl iodide on asparagine. Amer. chem. J. 6, 419–422 (1885)Google Scholar
  21. Nozaki, K.: Cis-trans isomerizations. II. The mechanism of the amine-catalyzed isomerization of diethyl maleate. J. Amer. chem. Soc. 63, 2681–2683 (1941)Google Scholar
  22. Nozaki, K., Ogg, R., Jr.: Cis-trans-isomerizations. I. The mechanism of a catalyzed isomerization of maleic acid to fumaric acid. J. Amer. chem. Soc. 63 2583–2586 (1941)Google Scholar
  23. Olson, A. R., Hudson, F. L.: The photostationary states of some geometrically isomeric acids. J. Amer. chem Soc. 55, 1410–1424 (1933)Google Scholar
  24. Stanier, R. Y., Palleroni, N. J., Doudoroff, M. J.: The aerobic pseudomonads: A taxonomic study. J. gen. Microbiol. 43, 159–271 (1966)Google Scholar

Copyright information

© Springer-Verlag 1976

Authors and Affiliations

  • E. J. Behrman
    • 1
  1. 1.Department of BiochemistryThe Ohio State UniversityColumbusUSA

Personalised recommendations