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Stoffwechselprodukte von Mikroorganismen

88. Mitteilung Zur Wirkungsweise des L-2,5-Dihydrophenylalanins — eines Phenylalaninantagonisten

Metabolic products of microorganisms

88. Mechanism of action of L-2,5-dihydrophenylalanine—an antagonist of phenylalanine

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Summary

L-2,5-Dihydrophenylalanine inhibits the growth of E. coli K 12 in synthetic liquid media when added during the lag phase at a concentration of 5×10-5 M (8.35 γ/ml). The inhibition is reversed uncompetetively by phenylalanine and competetively by tyrosine.

Mutants resistant to 10-3 M dl-p-fluorophenylalanine show cross-resistance to L-2,5-dihydrophenylalanine.

The bacteriostatic action of L-2,5-dihydrophenylalanine is caused by the fact that it interferes with the regulation of the biosynthesis of the aromatic amino acids as an antimetabolite of phenylalanine, similar to p-fluorophenylalanine.

L-2,5-Dihydrophenylalanine inhibits the activity of the phe-sensitive isoenzyme of the DAHP-synthetase for 72% at a concentration of 10-3 M. The activity of the prephenate dehydratase is inhibited for 66% at this concentration.

The synthesis of the DAHP-synthetase of E. coli K12 is repressed (30%) when L-2,5-dihydrophenylalanine is added to the culture medium at a concentration of 5×10-5 M.

A possible incorporation of L-2,5-dihydrophenylalanine into protein is discussed.

Zusammenfassung

L-2,5-Dihydrophenylalanin hemmt bei Zugabe in der lag-Phase das Wachstum von E. coli K 12 in definiertem, flüssigen Medium bei einer Konzentration von 5×10-5 M (8,35 γ/ml). Die Hemmwirkung wird von Phenylalanin unkompetitiv und von Tyrosin kompetitiv aufgehoben.

Mutanten, die resistent sind gegen 10-3 M dl-p-Fluorphenylalanin zeigen Kreuzresistenz gegen L-2,5-Dihydrophenylalanin.

Die bakteriostatische Wirkung von L-2,5-Dihydrophenylalanin auf E. coli K 12 beruht darauf, daß es ähnlich wie p-Fluorphenylalanin als Phenylalanin-Antimetabolit in die Regulation der Biosynthese der aromatischen Aminosäuren eingreift.

L-2,5-Dihydrophenylalanin hemmt die Aktivität des Phe-sensitiven Isoenzyms der DAHP-Synthetase bei einer Konzentration von 10-3 M zu 72%. Die Aktivität der Prephenatdehydratase wird bei dieser Konzentration zu 66% gehemmt.

Bei Zugabe von 5×10-5 M L-2,5-Dihydrophenylalanin zum Kulturmedium von E. coli K 12 wird die Bildung der DAHP-Synthetase zu 30% reprimiert.

Ein möglicher Einbau von L-2,5-Dihydrophenylalanin ins Protein wird diskutiert.

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Author notes

  1. U. Fickenscher

    Present address: Gesellschaft für molekularbiologische Forschung mbH, Stöckheim bei Braunschweig

Authors and Affiliations

  1. Institut für Biologie, Lehrbereich Mikrobiologie, Universität Tübingen, Tübingen, Deutschland

    U. Fickenscher & H. Zähner

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  1. U. Fickenscher
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  2. H. Zähner
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Additional information

87. Mitt.: U. Fickenscher, W. Keller-Schierlein u. H. Zähner: L-2,5-Dihydrophenylalanin. Arch. Mikrobiol. 75, 346–352 (1971).

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Fickenscher, U., Zähner, H. Stoffwechselprodukte von Mikroorganismen. Archiv. Mikrobiol. 76, 28–46 (1970). https://doi.org/10.1007/BF00409312

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