Stoffwechselprodukte von Mikroorganismen

Dähn, U.; Hagenmaier, Hanspaul; Höhne, Herbert; König, W. A.; Wolf, Grace; Zähner, H

doi:10.1007/bf00446834

Cited by 231 publications

(33 citation statements)

References 37 publications

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“…(Dahn et al, 1976), are strong inhibitors of chitin synthase (UDP-2-acetamido-2-deoxy-D-glucose : chitin 4-~-acetamidodeoxy-~glucosyl-transferase, EC 2.4.1 .16) in the pathogenic fungus Candida albicans (McCarthy et al, 1985). Since this enzyme does not exist in mammalian cells, nikkomycins are considered as promising potential antifungals of low toxicity for mammals.…”

Section: Introductionmentioning

confidence: 99%

Synergistic action of nikkomycin X/Z with azole antifungals on Candida albicans

Milewski

Mignini

Borowski

1991

Journal of General Microbiology

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Section: Introductionmentioning

confidence: 99%

Synergistic action of nikkomycin X/Z with azole antifungals on Candida albicans

Milewski

Mignini

Borowski

1991

Journal of General Microbiology

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“…Conversely, reduction at the ketal carbon (C-7') results in formation of the anhydro ring structure of octosyl acid (2). The same biosynthetic pathway seems to be realized in case of nikkomycins.…”

Section: Discussionmentioning

confidence: 89%

Metabolic products of microorganisms. 263 Nikkomycins Sz, Sx, Soz and Sox, new intermediates associated to the nikkomycin biosynthesis of Streptomyces tendae.

Schüz¹,

Fiedler²,

Zähner³

et al. 1992

J. Antibiot.

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New intermediates associated with nikkomycin biosynthesis, called nikkomycins Sz, Sx, Soz and Sox, were isolated and characterized from the culture broth of Streptomyces tendae Tii 901/S 2566. They are analogues to octosyl acids, shunt metabolites of polyoxin biosynthesis. The decreasing amounts of nikkomycins Sz and Sx, produced in the culture medium,shows a significant correlation to the increasing amounts of the biologically active nikkomycins Z and X, dependent on the increasing concentration of iron.Nikkomycins belong to the group of nucleoside peptide antibiotics2* which act as potent competitive inhibitors of fungal and insect chitin synthase3~8) (Fig. 1). More than 20 biologically active nikkomycin structures have been isolated from the culture filtrates of Streptomyces tendae strains (reviewed by Fiedler, 19899)). The biosynthesis of nikkomycins has been investigated by feeding labeled precursors to the mycelia. It is known that the pyridyl residue and the attached carbon atom of the amino acid moiety resulted from L-lysine10). The imidazolone base of nikkomycinsoriginates from histidine1 1}. For the aminohexuronicacid structure a similar mechanismwas discussed, as described for the structurally related polyoxins12sl3). This paper describes the fermentation and isolation of intermediates correlated to the biosynthesis of the nucleoside moiety, especially the aminohexuronic acid of the nikkomycins. Seeref1.

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“…4 Acetamido-or amino-ketone derivatives are important for their biological and pharmaceutical properties, 5,6 and in the preparation of antibiotic drugs such as nikkomycine or neopolyoxines. 7,8 The best known route for the synthesis of this class of compounds is the Dakin-West reaction, 9 the condensation of an α-amino acid with acetic anhydride in the presence of a base provides the α-acetamido ketones via an azalactone intermediate. 10 The simple and direct method for the synthesis of β-acetamido ketones reported by Iqbal and coworkers in 1994 involves the one-pot condensation of a ketone, aldehyde and acetonitrile in the presence of acetyl chloride.…”

Section: Introductionmentioning

confidence: 99%