Abstract
Pyrrolnitrin, a new antifungal compound produced by a Pseudomonas culture, was reported by Arima and co-workers (1964). Chemical degradation of the molecule by Imanaka et al. (1965 a) established the structure as 3-chloro-4-(2′-nitro-3′-chlorophenyl)-pyrrole (I); this structure was confirmed by synthesis in the Research Laboratories of Fujisawa Pharmaceutical Co., Ltd., Osaka, Japan (Nakano et al., 1966).
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References
Arima, K., H. Imanaka, M. Kousaka, A. Fukuda, and G. Tamura: Pyrrolnitrin, a new antibiotic substance produced by Pseudomonas. Agr. Biol. Chem. 28, 575 (1964).
Arima, K., H. Imanaka, M. Kousaka, A. Fukuda, and G. Tamura: Studies On pyrrolnitrin, a new antibiotic. I. Isolation and properties of pyrrolnitrin. J. Antibiotics (Japan), Ser. A 18, 201 (1965).
Birch, A. J., P. Hodge, R. W. Rickards, R. Takeda, and T. R. Watson: The structure of pyoluteorin. J. Chem. Soc. 1964, 2641.
Burkholder, R. P., R. M. Pfister, and F. H. Leitz: Production of a pyrrole antibiotic by a marine bacterium. Appl. Microbiol. 14, 649 (1966).
Hashimoto, M., and K. Hattori: Oxypyrrolnitrin: A metabolite of Pseudomonas. Chem. amp; Pharm. Bull. 14, 1314 (1966a).
Hashimoto, M., and K. Hattori: Isopyrrolnitrin, a metabolite from Pseudomonas. Bull. Chem. Soc. Japan 39, 410 (1966b).
Imanaka, H., M. Kousaka, G. Tamura, and K. Arima: Studies on pyrrolnitrin, a new antibiotic. Iii. Structure of pyrrolnitrin. J. Antibiotics (Japan), Ser. A 18, 207 (1965a).
Imanaka, H., M. Kousaka, G. Tamura, and K. Arima: Studies on pyrrolnitrin, a new antibiotic. II. Taxonomic studies on pyrrolnitrin-producing strain. J. Antibiotics (Japan), Ser. A 18, 205 (1965b).
Kawai, S., K. Kobayashi, T. Oshima, and F. Egami. Studies on the oxidation of p-aminobenzoate to p-nitrobenzoate by Streptomyces thioluteus. Arch. Biochem. Biophys. 112, 537 (1965).
Lively, D., M. Gorman, M. Haney, and J. Mare: Metabolism of tryptophans by Pseudomonas aureofaciens. I. Biosynthesis of pyrrolnitrin. Sixth Interscience Conf. on Antimicrobial Agents and Chemotherapy, Philadelphia 1966. Abstracts p. 26.
Lovell, F. M.: The structure of a bromine-rich marine antibiotic. J. Am. Chem. Soc. 88, 4510 (1966).
Manske, R. H. F.: The alkaloids chemistry and physiology, vol. Viii, p. 27 and 581. The indole alkaloids. New York: Academic Press 1965.
Nakano, H., S. Umio, K. Kariyone, K. Tanaka, T. Kishimoto, H. Noguchi, I. Ueda, H. Nakamura, and Y. Morimoto: Total synthesis of pyrrolnitrin, a new antibiotic. Tetrahedron Letters No. 7, 737 (1966).
Nishida, M., T. Matsubara, and M. Watanabe. PyrrOlnitrin, a new antifungal antibiotic. Microbiological and toxicological observations. J. Antibiotics (Japan), Ser. A 18, 211 (1965).
Petty, M. A.: An introduction to the origin and biochemistry of microbial halometabolites. Bacteriol. Rev. 25, 111 (1961).
Takeda, R.: Pseudomonas pigments. I. Pyoluteorin, a new chlorine-containing pigment produced by Pseudomonas aeruginosa. Hakkô K6gaku Zasshi 36, 281 (1958). Chem. Abstr. 53, 8279g (1959).
Yanofsky, C.: The tryptophan synthetase system. Bacteriol. Rev. 24, 221 (1960).
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Gorman, M., Lively, D.H. (1967). Pyrrolnitrin: A New Mode of Tryptophan Metabolism. In: Gottlieb, D., Shaw, P.D. (eds) Biosynthesis. Antibiotics. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-38441-1_32
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DOI: https://doi.org/10.1007/978-3-662-38441-1_32
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