Stoffwechselprodukte von Mikroorganismen 226. Mitteilung Versuche zur Strukturaufklärung von Niphimycin, 3. Teil. Identität von Scopafungin mit Niphimycin I und Lage des Malonylrestes in Niphimycin und Copiamycin

Gassmann, Peter; Hagmann, Leonhard; Keller‐Schierlein, W.; Samain, D.

doi:10.1002/hlca.19840670309

Cited by 25 publications

(5 citation statements)

References 7 publications

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“… The structure of niphimycin A with two stereogenic centers at C36 and C38 assigned has been published. Stereochemical studies of amycin B, identified as demalonyl niphimycin A, resulted in the assignment of C21, C23, C25, C27 and C28 relative configuration. In this paper, we present our results, which allowed for the assignment of absolute configuration of chiral centers at C34 and C35 of niphimycin A.…”

Section: Introductionmentioning

confidence: 99%

Absolute configurations of C34 and C35 of antibiotic niphimycin A

Laskowski

Rafiński

Sowiński

et al. 2012

Magnetic Reson in Chemistry

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The relative configurations of four stereogenic centers of the C33-C42 fragment of niphimycin A were assigned as 2S*, 3R*, 4S* and 6S*, based upon (1)H NMR analysis with double-quantum filtered COSY and nuclear Overhauser spectroscopy experiments. These data were then correlated with absolute configurations at C36 and C38 of niphimycin A, which were declared previously as 36S and 38S [3]. This allowed for the assignment of the absolute configurations at C34 and C35 of niphimycin A as 34S and 35R.

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Section: Introductionmentioning

confidence: 99%

Absolute configurations of C34 and C35 of antibiotic niphimycin A

Laskowski

Rafiński

Sowiński

et al. 2012

Magnetic Reson in Chemistry

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“…Detailed bioinformatic analysis of the modular organization in this gene cluster suggested that it was responsible for the biosynthesis of the azalomycin-related macrolide niphimycin. − Guided by genome analysis, we identified four new niphimycin analogues, namely, niphimycins C–E ( 1 – 3 ) and 17- O -methylniphimycin ( 4 ), together with the known niphimycin Iα ( 5 ) and 19- O -malonylniphimycin ( 6 ), from the cultures of strain IMB7-145. Although the planar structures of the niphimycins were established more than 30 years ago, their absolute configurations have not been completely resolved to date. − , On the basis of a combination of detailed spectroscopic and bioinformatics analyses, we propose the full relative and absolute configurations of the niphimycins. Herein, we report the identification of the niphimycin biosynthetic gene cluster, elucidation of the structures of the new niphimycins, and characterization of their bioactivities.…”

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confidence: 99%

“…Although the planar structures of the niphimycins were established more than 30 years ago, their absolute configurations have not been completely resolved to date. [20][21][22]24 On the basis of a combination of detailed spectroscopic and bioinformatics analyses, we propose the full relative and absolute configurations of the niphimycins. Herein, we report the identification of the niphimycin biosynthetic gene cluster, elucidation of the structures of the new niphimycins, and characterization of their bioactivities.…”

mentioning

confidence: 99%

Identification and Proposed Relative and Absolute Configurations of Niphimycins C–E from the Marine-Derived Streptomyces sp. IMB7-145 by Genomic Analysis

Wang

et al. 2018

J. Nat. Prod.

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Analysis of the whole genome sequence of Streptomyces sp. IMB7-145 revealed the presence of seven type I polyketide synthase biosynthetic gene clusters, one of which was highly homologous to the biosynthetic gene cluster of azalomycin F. Detailed bioinformatic analysis of the modular organization of the PKS gene suggested that this gene is responsible for niphimycin biosynthesis. Guided by genomic analysis, a large-scale cultivation ultimately led to the discovery and characterization of four new niphimycin congeners, namely, niphimycins C-E (1-3) and 17-O-methylniphimycin (4). The configurations of most stereocenters of niphimycins have not been determined to date. In the present study, the relative configurations were elucidated by spectroscopic analysis, including J-based analysis and the CNMR database method. Further, the full absolute configurations of niphimycins were completely proposed for the first time based on biosynthetic gene cluster analysis of the ketoreductase and enoylreductase domains for hydroxy- and methyl-bearing stereocenters. Compounds 1, 3, 4, and niphimycin Iα (5) showed antimicrobial activity against methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci (MIC: 8-64 μg/mL), as well as cytotoxicity against the human HeLa cancer cell line (IC: 3.0-9.0 μM). In addition, compounds 1 and 5 displayed significant activity against several Mycobacterium tuberculosis clinical isolates (MIC: 4-32 μg/mL).

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“…Because oxygen atoms in the polyketide biosynthesis frequently originate from their C3-or C3-building blocks, the hydroxy groups at C9, C15, C23, C25, C27, C33, C35, and C37 in oasomycin B (1) should derive from the carboxy group of acetate. In the 13C NMR spectrum of 1, isolated from the sodium [ 1 -13C ,1802]acetate incorporation experiment, 12 carbon atoms showed significant [13C]-enrichments. Besides the identical labeling pattern to the sodium [l-13C]acetate feeding (Figure 1), unfortunately, no [180]-label was detectable, indicating a loss of the oxygen label during metabolic processes and/or polyketide biosynthesis.…”

Section: Resultsmentioning

confidence: 99%

Common Principles in Macrolactone (Marginolactone) Biosynthesis. Studies on the Desertomycin Family

Zerlin¹,

Thiericke²

1994

J. Org. Chem.

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Administration of sodium [13C]-labeled acetates and sodium [l-13C]propionate to cultures of Streptoverticillium baldacii subsp. netropse (strain FH-S 1625) proved the polyketide origin of the 42-membered macrolactone in oasomycin B (1), a member of the desertomycin family. In a series of feeding different amino acids as presumptive polyketide starters ornithine was found to embody the initiator of the oasomycin biosynthesis, in which oxidative deamination, decarboxylation, and CoA-activation steps are involved. Resulting from the feeding of D,L-[l-13C]glucose, the D-mannose located at C22 of 1 derives from glucose via isomerization at C2 during carbohydrate metabolism. A fermentation in an [1802]-enriched atmosphere proved the oxidative deamination reaction during the macrolactone initiation. In addition, an oxygenase introduces the OH group at C22, which is used as the connecting site for the post-polyketide mannosylation step. Consequently, the glycosylation reaction as well as other characteristics of the desertomycin family's biosynthesis illuminate unexpected analogies and common principles in the formation of a number of related macrocyclic lactones. Due to the obvious biosynthetic relationships we introduce the term "marginolactones" for this class of actinomycetes macrolactones.

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Stoffwechselprodukte von Mikroorganismen 226. Mitteilung Versuche zur Strukturaufklärung von Niphimycin, 3. Teil. Identität von Scopafungin mit Niphimycin I und Lage des Malonylrestes in Niphimycin und Copiamycin

Cited by 25 publications

References 7 publications

Absolute configurations of C34 and C35 of antibiotic niphimycin A

Absolute configurations of C34 and C35 of antibiotic niphimycin A

Identification and Proposed Relative and Absolute Configurations of Niphimycins C–E from the Marine-Derived Streptomyces sp. IMB7-145 by Genomic Analysis

Common Principles in Macrolactone (Marginolactone) Biosynthesis. Studies on the Desertomycin Family

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