ArticleThe Journal of organic chemistry2014
Stereospecific synthesis of 23-hydroxyundecylprodiginines and analogues and conversion to antimalarial premarineosins via a Rieske oxygenase catalyzed bicyclization.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Chemoselective halogenation of premarineosin A for next-generation antimalarial development.Organic & biomolecular chemistry · 2026Article
- Metabolic engineering and late-stage functionalization expand the chemical space of the antimalarial premarineosin A.Communications chemistry · 2025Article
- Optimization of Prodiginines as Single-Dose Curative Antimalarials.Journal of medicinal chemistry · 2025Article
- Rieske Oxygenase-Catalyzed Biotransformations in Recombinant Cupriavidus necator Fueled by Formate Oxidation.Chembiochem : a European journal of chemical biology · 2025Article
- Rieske Oxygenases: Powerful Models for Understanding Nature's Orchestration of Electron Transfer and Oxidative Chemistry.Biochemistry · 2025Review
- A CRISPR-Cas9 system for knock-out and knock-in of high molecular weight DNA enables module-swapping of the pikromycin synthase in its native host.Microbial cell factories · 2025Article
- Tambjamines as Fast-Acting Multistage Antimalarials.ACS infectious diseases · 2024Article
- Optimization of B-Ring-Functionalized Antimalarial Tambjamines and Prodiginines.Journal of medicinal chemistry · 2024Article
- Discovery and Optimization of Tambjamines as a Novel Class of Antileishmanial Agents.Journal of medicinal chemistry · 2024Article
- Recent Advances in the Transition-Metal-Free Synthesis of Quinazolines.Molecules (Basel, Switzerland) · 2023Review
- Marine Pyrrole Alkaloids.Marine drugs · 2021Review
- Total Synthesis and Antimalarial Activity of 2-(Journal of medicinal chemistry · 2021Article
- The metabolic switch can be activated in a recombinant strain of Streptomyces lividans by a low oxygen transfer rate in shake flasks.Microbial cell factories · 2018Article
- PG-Priming Enhances Doxorubicin Influx to Trigger Necrotic and Autophagic Cell Death in Oral Squamous Cell Carcinoma.Journal of clinical medicine · 2018Article
- Oxidative cyclization of prodigiosin by an alkylglycerol monooxygenase-like enzyme.Nature chemical biology · 2017Article
- Inhibitory Growth of Oral Squamous Cell Carcinoma Cancer via Bacterial Prodigiosin.Marine drugs · 2017Article
- Natural Compounds from Herbs that can Potentially Execute as Autophagy Inducers for Cancer Therapy.International journal of molecular sciences · 2017Review
- MarH, a Bifunctional Enzyme Involved in the Condensation and Hydroxylation Steps of the Marineosin Biosynthetic Pathway.Organic letters · 2017Article
- Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products.Chemical reviews · 2016Review
- Synthesis and Structure-Activity Relationships of Tambjamines and B-Ring Functionalized Prodiginines as Potent Antimalarials.Journal of medicinal chemistry · 2015Article
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5 authors.
Funding
Abstract
Facile and highly efficient synthetic routes for the synthesis of (S)- and (R)-23-hydroxyundecylprodiginines ((23S)-2, and (23R)-2), 23-ketoundecylprodiginine (3), and deuterium-labeled 23-hydroxyundecylprodiginine ([23-d]-2) have been developed. We demonstrated a novel Rieske oxygenase MarG catalyzed stereoselective bicyclization of (23S)-2 to premarineosin A (4), a key step in the tailoring process of the biosynthesis of marineosins, using a marG heterologous expression system. The synthesis of various A-C-ring functionalized prodiginines 32-41 was achieved to investigate the substrate promiscuity of MarG. The two analogues 32 and 33 exhibit antimalarial and cytotoxic activities stronger than those of the marineosin intermediate 2, against Plasmodium falciparum strains (CQ(S)-D6, CQ(R)-Dd2, and 7G8) and hepatocellular HepG2 cancer cell line, respectively. Feeding of 34-36 to Streptomyces venezuelae expressing marG led to production of novel premarineosins, paving a way for the production of marineosin analogues via a combinatorial synthetic/biosynthetic approach. This study presents the first example of oxidative bicyclization mediated by a Rieske oxygenase.
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