Biogenetic amino acid antagonists

Nass, Gisela; Poralla, Karl; Zähner, Hans

doi:10.1007/bf01185604

Cited by 31 publications

(5 citation statements)

References 91 publications

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“…It has a broad antibiotic activity against Borrelia species, Sarcina lutea [10], some mouse tumors [11], Corynebacterium xerosis and some virus species in vitro, but not in vivo [12]. Studies of its mode of action demonstrated that borrelidin is an amino acid antagonist for L-threonine and homoserine and inhibits the enzymatic activity of threonyl-tRNA synthetase of Escherichia coli, Bacillus subtilis, B. polymyxa, Saccharomyces cerevisiae and the bean Phaseolus vulgaris [13].…”

Section: Resultsmentioning

confidence: 99%

Induction of aerial mycelium formation in a bld mutant of Streptomyces tendae by Borrelidinâa macrolide antibiotic

Schüz

Zähner

1993

FEMS Microbiology Letters

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In a screening programme for substances with morphogenic effects on the nikkomycin producer strain Streptomyces tendae Tü 901 we identified a metabolite, which induced aerial mycelium formation in the bld mutant Tü 901/S 2566‐EM 1. By using a HPLC UV/Vis absorbance spectral library we could confirm that this compound was identical with the macrolide antibiotic borrelidin. 100 ng borrelidin/paperdisc were sufficient to show an evident morphological effect.

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Section: Resultsmentioning

confidence: 99%

Induction of aerial mycelium formation in a bld mutant of Streptomyces tendae by Borrelidinâa macrolide antibiotic

Schüz

Zähner

1993

FEMS Microbiology Letters

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“…Possible causes for this resistance are: inefficient uptake of the analogues, lack of inhibition by analogues of the feedback-sensitive enzymes, inability of analogues to act as co-repressors, inefficacy of analogues as substrates or inhibitors of aminoacyl-tRNA synthetase, efficient degradation of analogues to non-toxic products (Fowden, Lewis & Tristram, 1967;Nass, Poralla & Zahner, 1971).…”

Section: Discussionmentioning

confidence: 99%

Arginine Analogues: Effect on Growth and on the First Two Enzymes of the Arginine Pathway in Pseudomonas aeruginosa

Leisinger

O'sullivan

Haas

1974

Journal of General Microbiology

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SUMMARYThe effect of 14 arginine analogues on the growth of Pseudomonas aeruginosa in a liquid mineral medium with either L-glutamate or L-ornithine as the sole carbon and nitrogen source was investigated. Two analogues, L-indospicine and L-arginine hydroxamate, inhibited growth markedly. The former was most effective in the ornithine medium and the latter only in the glutamate medium.The inhibition by arginine analogues of the first two enzymes of the arginine pathway, N-acetylglutamate synthetase and N-acetylglutamate 5-phosphotransferase, was studied. It was found that inhibition of these two feedback-sensitive enzymes did not correlate with inhibition of growth. O-(~-norvalyl-5)-isourea, which was a rather weak inhibitor of growth, was at least three times more active as an inhibitor of the enzymes than L-indospicine and L-arginine hydroxamate. These two analogues were about ten times less effective than L-arginine, the strongest inhibitor of both enzymes.

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“…[183] 2,5-Dihydrophenylalanin (55, Abbildung 22 D) ist eine andere g,d-ungesättigte Aminosäure, die als bakterieller Antimetabolit den Phe-Stoffwechsel stçren kann. [184] Eine weitere interessante Aminosäure aus der Gruppe natürlicher Diendihydroaminosäuren ist Gabaculin (56, Abbildung 22 D). [185] Die Biosynthese ist noch nicht aufgeklärt, aber der Reaktionsmechanismus mit einigen PLP-abhängigen Enzymen wurde untersucht.…”

Section: Aminosäuren Mit Potenziell Reaktiven Funktionellen Gruppenunclassified

Nichtproteinogene Aminosäurebausteine für Peptidgerüste aus nichtribosomalen Peptiden und hybriden Polyketiden

2013

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Frei vorkommende nichtproteinogene Aminosäuren sind schon lange wegen ihrer antimetabolen Eigenschaften bekannt. Entdeckt werden sie meist aufgrund der Reaktivität gegenüber der katalytischen Wirkung der Zielenzyme. Führt man sie regiospezifisch in biogene Peptide und Proteine ein, kann es möglich werden, eine neue Ära der Medizinalchemie an der Grenze zwischen kleinen und großen Wirkstoffen einzuleiten. Außerdem eröffnet die ortsspezifische Funktionalisierung von Proteinen besonders attraktive Strategien für die posttranslationale Proteinmodifizierung. Auch bieten viele der Aminosäuren, die von der Natur nicht für den Einbau in Proteine ausgewählt wurden, reiche architektonische Möglichkeiten bei Einführung in ribosomal hergestellte Polypeptide. Dieser Aufsatz fasst die Biosynthesewege zu den wichtigsten Klassen nichtkanonischer Bausteine und deren Stoffwechsellogik zusammen, die in nichtribosomalen Peptidgerüsten und nichtribosomalen Peptid‐Polyketid‐Hybriden resultieren.

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Biogenetic amino acid antagonists

Cited by 31 publications

References 91 publications

Induction of aerial mycelium formation in a bld mutant of Streptomyces tendae by Borrelidinâa macrolide antibiotic

Induction of aerial mycelium formation in a bld mutant of Streptomyces tendae by Borrelidinâa macrolide antibiotic

Arginine Analogues: Effect on Growth and on the First Two Enzymes of the Arginine Pathway in Pseudomonas aeruginosa

Nichtproteinogene Aminosäurebausteine für Peptidgerüste aus nichtribosomalen Peptiden und hybriden Polyketiden

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Biogenetic amino acid antagonists

Cited by 31 publications

References 91 publications

Induction of aerial mycelium formation in a bld mutant of Streptomyces tendae by Borrelidinâa macrolide antibiotic

Induction of aerial mycelium formation in a bld mutant of Streptomyces tendae by Borrelidinâa macrolide antibiotic

Arginine Analogues: Effect on Growth and on the First Two Enzymes of the Arginine Pathway in Pseudomonas aeruginosa

Nichtproteinogene Aminosäurebausteine für Peptidgerüste aus nichtribosomalen Peptiden und hybriden Polyketiden

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Induction of aerial mycelium formation in a bld mutant of Streptomyces tendae by Borrelidinâa macrolide antibiotic

Induction of aerial mycelium formation in a bld mutant of Streptomyces tendae by Borrelidinâa macrolide antibiotic