ArticleApplied and environmental microbiology2011
Development of a Streptomyces venezuelae-based combinatorial biosynthetic system for the production of glycosylated derivatives of doxorubicin and its biosynthetic intermediates.
Article in Applied and environmental microbiology, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 61 citations in OpenAlex.
- Complete Pathway Refactoring and Combinatorial Biosynthesis of Anthracyclines for Modulation of Histone Eviction and DNA Damage Bioactivities.Angewandte Chemie (International ed. in English) · 2026Article
- Biodiscovery ofMicrobial genomics · 2025Article
- Study of the potential forSustainable chemistry for climate action · 2025Article
- Synthetic Biology in Natural Product Biosynthesis.Chemical reviews · 2025Review
- Metabolic engineering ofFrontiers in bioengineering and biotechnology · 2024Article
- Rational Design of Daunorubicin C-14 Hydroxylase Based on the Understanding of Its Substrate-Binding Mechanism.International journal of molecular sciences · 2023Article
- Rethinking Biosynthesis of Aclacinomycin A.Molecules (Basel, Switzerland) · 2023Review
- Article
- Functional Characterization of a Regiospecific Sugar-Applied and environmental microbiology · 2022Article
- Article
- AACS synthetic biology · 2021Article
- Pathway Engineering of Anthracyclines: Blazing Trails in Natural Product Glycodiversification.The Journal of organic chemistry · 2020Article
- Identification and Characterization of a NovelMolecules (Basel, Switzerland) · 2020Article
- Pigments from Soil Bacteria and Their Therapeutic Properties: A Mini Review.Current microbiology · 2019Review
- Improvement of the pharmacological activity of menthol via enzymatic β-anomer-selective glycosylation.AMB Express · 2017Article
- Diversifying Natural Products with Promiscuous Glycosyltransferase Enzymes via a Sustainable Microbial Fermentation Approach.Frontiers in chemistry · 2017Article
- Engineering microbial hosts for production of bacterial natural products.Natural product reports · 2016Review
- Thioesterase domain swapping of a linear polyketide tautomycetin with a macrocyclic polyketide pikromycin in Streptomyces sp. CK4412.Journal of industrial microbiology & biotechnology · 2016Article
- Accessing Nature's diversity through metabolic engineering and synthetic biology.F1000Research · 2016Review
- Tailoring pathway modularity in the biosynthesis of erythromycin analogs heterologously engineered in E. coli.Science advances · 2015Article
Corrections and comments
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Authors and funding
10 authors at 4 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Doxorubicin, one of the most widely used anticancer drugs, is composed of a tetracyclic polyketide aglycone and l-daunosamine as a deoxysugar moiety, which acts as an important determinant of its biological activity. This is exemplified by the fewer side effects of semisynthetic epirubicin (4'-epi-doxorubicin). An efficient combinatorial biosynthetic system that can convert the exogenous aglycone ε-rhodomycinone into diverse glycosylated derivatives of doxorubicin or its biosynthetic intermediates, rhodomycin D and daunorubicin, was developed through the use of Streptomyces venezuelae mutants carrying plasmids that direct the biosynthesis of different nucleotide deoxysugars and their transfer onto aglycone, as well as the postglycosylation modifications. This system improved epirubicin production from ε-rhodomycinone by selecting a substrate flexible glycosyltransferase, AknS, which was able to transfer the unnatural sugar donors and a TDP-4-ketohexose reductase, AvrE, which efficiently supported the biosynthesis of TDP-4-epi-l-daunosamine. Furthermore, a range of doxorubicin analogs containing diverse deoxysugar moieties, seven of which are novel rhodomycin D derivatives, were generated. This provides new insights into the functions of deoxysugar biosynthetic enzymes and demonstrates the potential of the S. venezuelae-based combinatorial biosynthetic system as a simple biological tool for modifying structurally complex sugar moieties attached to anthracyclines as an alternative to chemical syntheses for improving anticancer agents.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.