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Bioscience, Biotechnology, and Biochemistry Volume 64, 2000 - Issue 3
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Original Articles

Biosynthesis of Violacein: Intact Incorporation of the Tryptophan Molecule on the Oxindole Side, with Intramolecular Rearrangement of the Indole Ring on the 5-Hydroxyindole Side

A. Z. M. Ruhul MOMENDepartment of Applied Biological Chemistry, Faculty of Agriculture, and Graduate School of Science and Technology, Niigata University
&
Tsutomu HOSHINODepartment of Applied Biological Chemistry, Faculty of Agriculture, and Graduate School of Science and Technology, Niigata University
Pages 539-549 | Received 27 Sep 1999, Accepted 10 Nov 1999, Published online: 22 May 2014

  • 1) Demoss, R. D. and Happel, M. E., Nutritional requirements of Chromobacterium violaceum. J. Bacteriol., 77, 137-141 (1958).
  • 2) Demoss, R. D. and Evans, N. R., Incorporation of C14-labeled substrate into violacein. J. Bacteriol., 79, 729-733 (1960).
  • 3) Hoshino, T., Kondo, T., Uchiyama, T., and Ogasawara, N., Biosynthesis of violacein: a novel rearrangement in tryptophan metabolism with a 1,2-shift of the indole ring. Agric. Biol. Chem., 51, 965-968 (1987).
  • 4) Hoshino, T., Takano, T., Hori, S., and Ogasawara, N., Biosynthesis of violacein: origin of hydrogen, nitrogen and oxygen atom in the 2-pyrrolidone nucleus. Agric. Biol. Chem., 51, 2733-2741 (1987).
  • 5) Hagmann, M. and Grisebach, H., Enzymatic rearrangement of flavanone to isoflavone. FEBS Lett., 175, 199 (1984).
  • 6) Pember, S.O., Villafranca, J.J., and Benkovic, S., Phenylalanine hydroxylase from Chromobacterium violaceum is a copper-containing monooxygenase. Kinetics of the reductive activation of the enzyme. Biochemistry, 25, 6611-6619 (1986).
  • 7) Hoshino, T., Hayashi, T., and Odajima, T., Biosynthesis of violacein: oxygenation at the 2-position of the indole ring and structures of proviolacein, prodeoxyviolacein and pseudoviolacein, the plausible biosynthetic intermediates of violacein and deoxyviolacein. J. Chem. Soc. Perkin Trans. 1, 1565-1571 (1995).
  • 8) Hoshino, T., and Yamamoto, M., Conversion from tryptophan precursor into violacein pigment by a cell-free system from Chromobacterium violaceum. Biosci. Biotechnol. Biochem., 61, 2134-2136 (1997).
  • 9) Ruhul Momen, A. Z. M., Mizuoka, T., and Hoshino, T., Studies of biosynthesis of violacein. Part 9. Green pigment possessing tetraindole and dipyrromethene moieties, chromoviridans and deoxychromoviridans, produced by a cell-free extract of Chromobacterium violaceum and their biosynthetic origin. J. Chem. Soc., Perkin Trans. 1, 3087-3092 (1998).
  • 10) Higuma, M., Nikaidou, N., Kanai, Y., Watanabe, T., and Hoshino, T., Cloning of a gene cluster responsible for the biosynthesis of violacein. Ann. Meeting of Japan Soc. for Biosci. Biotechnol. and Agrochem., Abstract p. 232, August 1995.
  • . 1958. p. 249- 252.
  • . 1981. p. 172.
  • 13) Savige, W. E. and Fontana, A., New procedure for oxidation of 3-substituted indoles to oxindole: modification of tryptophan residues in peptides and proteins. J. Chem. Soc. Chem. Commun., 599-600 (1976).
  • 14) Hoshino, T., Yamamoto, M., and Uchiyama, T., Formations of (5-hydroxy)indole S-(-)lactic acid, N-acetyl-5-hydroxy-L-tryptophan, and (5-hydroxy) indole carboxylic acid in the metabolism of tryptophan and 5-hydroxytryptophan by Chromobacterium violaceum. Biosci. Biotechnol. Biochem., 57, 1609-1610 (1993).
  • 15) Hoshino, T., Kojima, Y., Hayashi, T., Uchiyama, T., and Kaneko, K., A new metabolite of tryptophan, chromopyrrolic acid, produced by Chromobacterium violaceum. Biosci. Biotechnol. Biochem., 57, 775-781 (1993).
  • 16) Hoshino, T., Hayashi, T., and Uchiyama, T., Pseudodeoxyviolacein, a new red pigment produced by the tryptophan metabolism of Chromobacterium violaceum. Biosci. Biotechnol. Biochem., 58, 279-282 (1994).
  • 17) Hoshino, T. and Ogasawara, N., Biosynthesis of violacein: evidence for the intermediacy of 5-hydroxy-L-tryptophan and the structure of a new pigment, oxyviolacein, produced by the metabolism of 5-hydroxytryptophan. Agric. Biol. Chem., 54, 2339-2346 (1990).
  • 18) Amrhein, N., Biosynthesis of cyanidin in buckwheat hypocotyls. Phytochemistry, 18, 585-589 (1979).

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