Zur Biogenese des Xanthocillins, II1: Die Herkunft des Stickstoffs der Isonitril-Gruppen

Achenbach, Hans; König, F.

doi:10.1007/bf02136667

Cited by 7 publications

(3 citation statements)

References 3 publications

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“…This pathway occurs mainly in fungi and bacteria. Historically, early studies on xanthocillin allowed for the discovery of this path by feeding Penicilllum notatum strains with tyrosine-2- 14 C– 15 N and in turn isolating 15 N xanthocillin . Recently two genes involved in the synthesis of the indole antibiotic B371 ( 11 ) named isnA and isnB revealed the origin of the isocyano group.…”

Section: Isocyano Group In Natural Productsmentioning

confidence: 99%

“…Historically, early studies on xanthocillin allowed for the discovery of this path by feeding Penicilllum notatum strains with tyrosine-2-14 C− 15 N and in turn isolating 15 N xanthocillin. 64 Recently two genes involved in the synthesis of the indole antibiotic B371 (11) named isnA and isnB revealed the origin of the isocyano group. These two enzymes are generally known as isonitrile synthases (ISNs) or isocyanide synthases (ICSs), and they can convert the amino group of aromatic amino acids into an isocyanide.…”

Section: Biosynthetic Origin and The Ecological Role Of Isocyanidementioning

confidence: 99%

“…Early studies on the metabolic origin of xanthocillin X demonstrated that the isocyanide nitrogen atom derives from tyrosine. 64 Unsurprisingly, xanthocillin X proved to possess a potent antibiotic activity against both Gram positive and Gram negative bacteria, as well as against yeasts and fungi, inducing slow onset of bacterial resistance in serial passages (Table 2). 82−84 It was sold for more than 15 years under the commercial name of Brevicid and used as topical antibiotic.…”

Section: Isocyanides In Fungi and Their Biological Activitymentioning

confidence: 99%

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Medicinal Chemistry of Isocyanides

et al. 2021

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In eons of evolution, isocyanides carved out a niche in the ecological systems probably thanks to their metal coordinating properties. In 1859 the first isocyanide was synthesized by humans and in 1950 the first natural isocyanide was discovered. Now, at the beginning of XXI century, hundreds of isocyanides have been isolated both in prokaryotes and eukaryotes and thousands have been synthesized in the laboratory. For some of them their ecological role is known, and their potent biological activity as antibacterial, antifungal, antimalarial, antifouling, and antitumoral compounds has been described. Notwithstanding, the isocyanides have not gained a good reputation among medicinal chemists who have erroneously considered them either too reactive or metabolically unstable, and this has restricted their main use to technical applications as ligands in coordination chemistry. The aim of this review is therefore to show the richness in biological activity of the isocyanidecontaining molecules, to support the idea of using the isocyanide functional group as an unconventional pharmacophore especially useful as a metal coordinating warhead. The unhidden hope is to convince the skeptical medicinal chemists of the isocyanide potential in many areas of drug discovery and considering them in the design of future drugs.

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Section: Isocyano Group In Natural Productsmentioning

confidence: 99%

Section: Biosynthetic Origin and The Ecological Role Of Isocyanidementioning

confidence: 99%

Section: Isocyanides In Fungi and Their Biological Activitymentioning

confidence: 99%

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Medicinal Chemistry of Isocyanides

et al. 2021

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Zur Biogenese des Xanthocillins, III Die Frage der biogenetischen Gleichwertigkeit der beiden Xanthocillin‐Hälften

Achenbach

König

1972

Chem. Ber.

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Die Frage der biogenetischen Gleichwertigkeit der beiden Xanthocillin-HalftenDie Bildung von monomarkiertem und dimarkiertem Xanthocillin-X (1) durch P. notutuin Westling wurde nach Gabe von [lSN]Tyrosin studiert. Die Ergebnisse widersprechen der Entstehung von 1 durch Kupplung zweier Cs-Cz-N-Einheiten aus Tyrosin: In dem symmetrischen Xanthocillin-Molekiil stammt nur ein Stickstoffatom direkt aus Tyrosin. -Gegenwart von p-Hydroxy-phenylbrenztraubensaure bewirkt eine signifikante Erhohung der Isotopenanreicherung in 1 bei gleichzeitiger Unterdriickung der Bildung dimarkierter Spezies. Wir schlieBen daraus, daR diese Ketosaure neben Tyrosin an der Biogenese des Xanthocillins beteiligt ist. -Einbauversuche mit [3-2Hz]Tyrosin bestatigen die Resultate. Biogenesis of XaothocWm, In') The Problem of Biogenetic Equivalence of the two C6-Cz-N-PartS in the Xanthocillim MoleculeAfter addition of [lSNltyrosine to cultures of P. nofatum Westling the formation of monolabelled and dilabelled xanthocil1in:X (1) was studied. The results are in disagreement with the formation of 1 by coupling of two C6-C2-N units from tyrosine: Only one nitrogen atom in the symmetric xanthocillin molecule originates directly from tyrosine. -The presence of p-hydroxyphenylpyruvic acid causes a significant increase of isotope enrichment in 1 and simultaneously a decrease of formation of dilabelled species. Thus we conclude, that besides tyrosine this keto acid is envolved in the biogenesis of xanthocillin. -Incorporation experiments using [3-2Hz]tyrosine corroborate these results.

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The Biosynthesis of Some Miscellaneous Mycotoxins

Vleggaar¹,

Steyn²

1980

The Biosynthesis of Mycotoxins

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Zur Biogenese des Xanthocillins, II1: Die Herkunft des Stickstoffs der Isonitril-Gruppen

Cited by 7 publications

References 3 publications

Medicinal Chemistry of Isocyanides

Medicinal Chemistry of Isocyanides

Zur Biogenese des Xanthocillins, III Die Frage der biogenetischen Gleichwertigkeit der beiden Xanthocillin‐Hälften

The Biosynthesis of Some Miscellaneous Mycotoxins

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