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A crystalline pigment produced from 2-hydroxypyridine by arthrobacter crystallopoietes n.sp.

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Summary

A bacterium was isolated from soil which utilizes 2-hydroxypyridine as sole source of carbon and nitrogen. When grown on solid medium with this substrate massive amounts of green rectangular crystals are deposited extracellularly in the colony mass. The pigment producing organism proved to be a hitherto undescribed species to which the name Arthrobacter crystallopoietes was applied. The pigment formed is characterized qualitatively by the following properties: it is an oxidation product of 2-hydroxypyridine probably still containing a six-membered heterocyclic ring; it exists as an anion with an intense blue color in neutral or slightly alkaline solution and as a metal salt in the deposited crystals; it precipitates from acid solution as a red water-insoluble free acid; it can be reversible oxidized and reduced, being colorless in the reduced form; and in solution it is spontaneously oxidized by air, the reaction being very rapid at alkalineph. The ultraviolet, visible and infrared spectra of the blue and red forms are presented. The properties of the pigment show that it is a member of a chemically poorly defined group of compounds termed azaquinones and that it is related to but not identical with pigments produced by the bacterial oxidation of nicotine, nicotinic acid and isonicotinic acid.

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References

  • Ames, D. E., R. E. Bowman and T. F. Grey: Synthesis of some methylsubstituted 2:3:6-trihydroxypyridines. J. chem. Soc. 1953, 3008–3015.

  • Behrman, E. J. and B. M. Pitt: The Elbs peroxydisulfate oxidation in the pyridine series: a new synthesis of 2,5-dihydroxypyridine. J. Amer. chem. Soc. 80, 3717–3718 (1958).

    Google Scholar 

  • —, and R. Y. Stanier: The bacterial oxidation of nicotinic acid. J. biol. Chem. 228, 923–945 (1957).

    Google Scholar 

  • Behrmann, A., u. A. W. Hofmann: Über die Amide der Citronensäure; Umwandlung derselben in Pyridinverbindungen. Chem. Ber. 17, 2681–2699 (1984).

    Google Scholar 

  • Boyer, J. H., and S. Kruger: Azaquinones. I. Oxidation of certain hydroxy- and aminopyridones. J. Amer. chem. Soc. 79, 3552–3554 (1957).

    Google Scholar 

  • Breed, R. S., E. G. D. Murray and N. R. Smith: Bergey's Manual of Determinative Bacteriology. Baltimore: Williams and Wilkins, Seventh Edition, 1957.

    Google Scholar 

  • Bucherer, H.: Über den mikrobiellen Abbau von Giftstoffen. I. Über den mikrobiellen Abbau von Nicotin. Zbl. Bakt., II. Abt. 105, 166–173 (1942).

    Google Scholar 

  • Conn, H. J. (Editor): Manual of Microbiological Methods. Society of American Bacteriologists, Committee on Bacteriological Technic. New York: McGraw-Hill, 1957.

    Google Scholar 

  • —, and I. Dimmick: Soil bacteria similar in morphology to Mycobacterium and Corynebacterium. J. Bact. 54, 291–303 (1947).

    Google Scholar 

  • Ensign, J. C.: The bacterial metabolism of pyridine, 2-hydroxypyridine and nicotinic acid. Dissertation, University of Southern California, Los Angeles, 1963.

    Google Scholar 

  • Ensign, J. C., and S. C. Rittenberg: A new pathway for nicotinic acid oxidation involving the production of a soluble blue pigment. Bact. Proc. 1962, 107.

  • Ensign, J. C., S. C. Rittenberg: Blue pigment production during isonicotinic acid production. Bact. Proc. 1963, 54

  • Errera, G.: Über Pyridinderivate aus Cyanessigester. Chem. Ber. 31, 1241–1246 (1898).

    Google Scholar 

  • Gherna, R. L., and S. C. Rittenberg: Alternate pathways in nicotine degradation. Bact. Proc. 1962, 107.

  • Hess, A.: Einige Derivate des Picolins. Chem. Ber. 32, 1985–1987 (1899).

    Google Scholar 

  • Kuhn, D. A., u. M. D. Starr: Arthrobacter atrocyaneus, n. sp., and its blue pigment Arch. Mikrobiol. 36, 175–181 (1960).

    Google Scholar 

  • Kundernatsch, R.: Über die directe Einführung von Hydroxyl in das β-Oxypyridin. Mh. Chem. 18, 613–628 (1897).

    Google Scholar 

  • Lochhead, A. G.: Two new species of Arthrobacter requiring respectively vitamin-B12 and the terregens factor. Arch. Mikrobiol. 31, 163–178 (1958).

    Google Scholar 

  • Moore, J. A., and F. J. Morascia: Heterocyclic studies. VII. The preparation and reactions of 2-amino-5-hydroxypyridines; the formation of an azaquinone. J. Amer. chem. Soc. 81, 6049–6056 (1959).

    Google Scholar 

  • Ost, H.: Stickstoffhaltige Derivate der Mekonsäure und ihre Umwandlung in Pyridin. J. parkt. Chem. 27, 257–294 (1883).

    Google Scholar 

  • Rogerson, H., and J. F. Thorpe: Some alkyl derivatives of glutaconic acid and of 2:6-dihydroxypyridine. J. chem. Soc. 87, 1685–1714 (1905).

    Google Scholar 

  • Ruhemann, S.: Formation of γγ'-dihydroxypyridine. J. chem. Soc. 73, 350–353 (1896).

    Google Scholar 

  • Schippers-Lammertse, A. F., A. O. Muijsers and K. B. Klatser-Oedekerk: Arthrobacter polychromogenes nov. spec., its pigments, and a bacteriophage of this species. Antonie v. Leuwenhoek 29, 1–15 (1963).

    Google Scholar 

  • Schroeter, G., C. Seidler, M. Sulzbacher u. R. Kanitz: Über die spontane Polymerisation von Cyan-essigsäurechlorid, eine einfache Synthese des Alkaloids Ricinin. Chem. Ber. 65, 432–445 (1932).

    Google Scholar 

  • Sell, W. J., and T. H. Easterfield: Studies on citrazinic acid. Part I. J. chem. Soc. 63, 1035–1051 (1893).

    Google Scholar 

  • Sguros, D. L.: Taxonomy and nutrition of a new species of nicotinophilic bacterium. Bact. Proc. 1955, 21–22.

  • Skerman, V. B. D.: A Guide to the Identification of the Genera of Bacteria. Baltimore: Williams and Wilkins 1959.

    Google Scholar 

  • Umbreit, W. W., R. H. Burris and J. P. Staufer: Manometric Techniques and Tissue Metabolism. Minneapolis: Burgess 1959.

    Google Scholar 

  • Wenusch, A.: Further studies of a biological decomposition of nicotine. Untersuch. Lebensm. 84, 498–501 (1942).

    Google Scholar 

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This investigation was supported in part by grants G9882 and GB736 from the National Science Foundation.

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Ensign, J.C., Rittenberg, S.C. A crystalline pigment produced from 2-hydroxypyridine by arthrobacter crystallopoietes n.sp.. Archiv. Mikrobiol. 47, 137–153 (1963). https://doi.org/10.1007/BF00422519

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