Journal ArticleDOI
Biosynthetic origins of the polycyclic xanthone antibiotic, citreamicin
Guy T. Carter,Donald B. Borders,Joseph J. Goodman,Joseph Ashcroft,Michael Greenstein,William M. Maiese,Cedric J. Pearce +6 more
TLDR
In this article, 13C-NMR spectroscopic analysis of the enriched products demonstrated a labelling pattern indicating that the antibiotic is derived from a polyketide which undergoes rearrangement by a mechanism unique for xanthone biosynthesis.Abstract:
The biosynthesis of citreamicin 1 has been studied by feeding 13C- and 18O-labelled precursors to Micromonospora citrea cultures. 13C-NMR spectroscopic analysis of the enriched products demonstrated a labelling pattern indicating that the antibiotic is derived from a polyketide which undergoes rearrangement by a mechanism unique for xanthone biosynthesis.read more
Citations
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Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis
Kye-Simeon Masters,Stefan Bräse +1 more
TL;DR: In this article, the authors describe the xanthones as "privileged structures" and describe methods for the construction of the (polysubstituted) unsaturated xanthone core.
Journal Article
Xanthones from fungi, lichens, and bacteria : the natural products and their synthesis
Kye-Simeon Masters,Stefan Bräse +1 more
TL;DR: The fascinating structural and biological properties of xanthone dimers and heterodimers may excite the synthetic or natural product chemist.
Journal ArticleDOI
Polycyclic xanthone natural products: structure, biological activity and chemical synthesis.
TL;DR: The aim of this article is to highlight the most recent developments of this subset of the xanthone family by detailing the innate challenges of the construction of this class of natural products, new synthetic approaches, and pharmacological data.
Journal ArticleDOI
Unveiling the Post-PKS Redox Tailoring Steps in Biosynthesis of the Type II Polyketide Antitumor Antibiotic Xantholipin
TL;DR: Findings may also apply to other polycyclic xanthone antibiotics, and they form the basis for genetic engineering of the xantholipin and similar biosynthetic gene clusters for the generation of compounds with improved antitumor activities.
Journal ArticleDOI
A Multifunctional Monooxygenase XanO4 Catalyzes Xanthone Formation in Xantholipin Biosynthesis via a Cryptic Demethoxylation
TL;DR: It is demonstrated that a flavin-dependent monooxygenase (FMO) XanO4 catalyzes the oxidative transformation of an anthraquinone to a xanthone system during the biosynthesis of xantholipin, and the reaction involves sequential insertion of two oxygen atoms, accompanied by an unexpected cryptic demethoxylation reaction.
References
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Natural abundance carbon-13-carbon-13 coupling observed via double-quantum coherence
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An NMR technique for tracing out the carbon skeleton of an organic molecule
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Improvement of pulse performance in N.M.R. coherence transfer experiments
TL;DR: In this paper, the principles of compensation of pulse imperfections in N.M.R. coherence transfer experiments are explained and the INADEQUATE technique in which 13C-13C satellites are observed through a double quantum filter is chosen for detailed theoretical analysis.
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Citreamicins, novel antibiotics from micromonospora citrea: isolation, characterization, and structure determination
TL;DR: A new family of antibacterial antibiotics has been isolated from Micromonospora citrea of the polycyclic xanthone structure type and their isolation, characterization and structure determination are presented.
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Metabolites of microorganisms. 162nd Communication. The crystal and molecular structure of lysolipin I
TL;DR: The triacetate of the antibiotic lysolipin crystallizes in the space group P21, where a = 11.059, b = 21.453, c = 8.453 and β = 109°.