ArticleJournal of the American Chemical Society2018
Integration of Genomic Data with NMR Analysis Enables Assignment of the Full Stereostructure of Neaumycin B, a Potent Inhibitor of Glioblastoma from a Marine-Derived Micromonospora.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed.
- Marine-Derived Rare Actinomycetes: Metabolites and Their Biosynthesis.Marine drugs · 2026Review
- NRPS and PKS pathways in actinomycetes: A review of biosynthetic diversity and bioactive potential.Current research in pharmacology and drug discovery · 2026Review
- Cyclization by Intramolecular Suzuki-Miyaura Cross-Coupling-A Review.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Catalytic Enantioselective C-C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents.Chemical reviews · 2024Review
- Article
- Rapid Synthesis of the Spiroketal Subunit of Neaumycin B: Stereochemical Aspects of Singly Anomeric Spiroketals and Proposal for a Stereocenter Reassignment.Organic letters · 2024Article
- Actinomycetota From Macroalgae as Rich Source for Natural Products Discovery Revealed Through Culture-Dependent and -Independent Approaches.Microbial biotechnology · 2024Article
- Bioinformatic prediction of the stereoselectivity of modular polyketide synthase: an update of the sequence motifs in ketoreductase domain.Beilstein journal of organic chemistry · 2024Article
- Synthesis of the C28-C41 Side Chain of (Proposed) Neaumycin B: A Contiguous Stereohextet.Organic letters · 2023Article
- Total Synthesis of the Reported Structure of Neaumycin B.Journal of the American Chemical Society · 2023Article
- Natural Products and Biological Activity from Actinomycetes Associated with Marine Algae.Molecules (Basel, Switzerland) · 2023Review
- Article
- Review
- Biomimetic Synthesis of Chejuenolides A-C by a Cryptic Lactone-Based Macrocyclization: Stereochemical Implications in Biosynthesis.ACS central science · 2023Article
- Ruthenium-Catalyzed Butadiene-Mediated Crotylation and Oxazaborolidine-Catalyzed Vinylogous Mukaiyama Aldol Reaction for The Synthesis of C1-C19 and C23-C35 of Neaumycin B.Angewandte Chemie (International ed. in English) · 2022Article
- Natural Marine Products: Anti-Colorectal Cancer In Vitro and In Vivo.Marine drugs · 2022Review
- Impact of novel microbial secondary metabolites on the pharma industry.Applied microbiology and biotechnology · 2022Review
- Natural Products from Actinomycetes Associated with Marine Organisms.Marine drugs · 2021Review
- Recent advances in the discovery of novel marine natural products and mycosporine-like amino acid UV-absorbing compounds.Applied microbiology and biotechnology · 2021Review
- Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments.Organic letters · 2021Article
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6 authors.
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Abstract
The microbial metabolites known as the macrolides are some of the most successful natural products used to treat infectious and immune diseases. Describing the structures of these complex metabolites, however, is often extremely difficult due to the presence of multiple stereogenic centers inherent in this class of polyketide-derived metabolites. With the availability of genome sequence data and a better understanding of the molecular genetics of natural product biosynthesis, it is now possible to use bioinformatic approaches in tandem with spectroscopic tools to assign the full stereostructures of these complex metabolites. In our quest to discover and develop new agents for the treatment of cancer, we observed the production of a highly cytotoxic macrolide, neaumycin B, by a marine-derived actinomycete bacterium of the genus Micromonospora. Neaumycin B is a complex polycyclic macrolide possessing 19 asymmetric centers, usually requiring selective degradation, crystallization, derivatization, X-ray diffraction analysis, synthesis, or other time-consuming approaches to assign the complete stereostructure. As an alternative approach, we sequenced the genome of the producing strain and identified the neaumycin gene cluster ( neu). By integrating the known stereospecificities of biosynthetic enzymes with comprehensive NMR analysis, the full stereostructure of neaumycin B was confidently assigned. This approach exemplifies how mining gene cluster information while integrating NMR-based structure data can achieve rapid, efficient, and accurate stereostructural assignments for complex macrolides.
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