ArticleApplied and environmental microbiology2011
Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties.
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 13 papers.
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Who cites it
13 citing papers in PubMed, 34 citations in OpenAlex.
- Synthetic Biology in Natural Product Biosynthesis.Chemical reviews · 2025Review
- Bioactive Angucyclines/Angucyclinones Discovered from 1965 to 2023.Marine drugs · 2025Review
- Chrysomycins, Anti-Tuberculosis C-Glycoside Polyketides fromMarine drugs · 2024Article
- Engineering BioBricks for Deoxysugar Biosynthesis and Generation of New Tetracenomycins.ACS omega · 2023Article
- Polycarcin V induces DNA-damage response and enables the profiling of DNA-binding proteins.National science review · 2022Article
- A comprehensive review of glycosylated bacterial natural products.Chemical Society reviews · 2015Review
- Tailoring pathway modularity in the biosynthesis of erythromycin analogs heterologously engineered in E. coli.Science advances · 2015Article
- Enzymatic basis of "hybridity" in thiomarinol biosynthesis.Angewandte Chemie (International ed. in English) · 2015Article
- Recent advances in combinatorial biosynthesis for drug discovery.Drug design, development and therapy · 2015Review
- Enzymatic methylation and structure-activity-relationship studies on polycarcin V, a gilvocarcin-type antitumor agent.Chembiochem : a European journal of chemical biology · 2014Article
- Synthetic biological approaches to natural product biosynthesis.Current opinion in biotechnology · 2012Review
- Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis.Natural product reports · 2012Review
- Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis.Angewandte Chemie (International ed. in English) · 2012Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
A combinatorial biosynthetic approach was used to interrogate the donor substrate flexibility of GilGT, the glycosyltransferase involved in C-glycosylation during gilvocarcin biosynthesis. Complementation of gilvocarcin mutant Streptomyces lividans TK24 (cosG9B3-U(-)), in which the biosynthesis of the natural sugar donor substrate was compromised, with various deoxysugar plasmids led to the generation of six gilvocarcin analogues with altered saccharide moieties. Characterization of the isolated gilvocarcin derivatives revealed five new compounds, including 4-β-C-D-olivosyl-gilvocarcin V (D-olivosyl GV), 4-β-C-D-olivosyl-gilvocarcin M (D-olivosyl GM), 4-β-C-D-olivosyl-gilvocarcin E (D-olivosyl GE), 4-α-C-L-rhamnosyl-gilvocarcin M (polycarcin M), 4-α-C-L-rhamnosyl-gilvocarcin E (polycarcin E), and the recently characterized 4-α-C-L-rhamnosyl-gilvocarcin V (polycarcin V). Preliminary anticancer assays showed that D-olivosyl-gilvocarcin and polycarcin V exhibit antitumor activities comparable to that of their parent drug congener, gilvocarcin V, against human lung cancer (H460), murine lung cancer (LL/2), and breast cancer (MCF-7) cell lines. Our findings demonstrate GilGT to be a moderately flexible C-glycosyltransferase able to transfer both D- and L-hexopyranose moieties to the unique angucyclinone-derived benzo[D]naphtho[1,2b]pyran-6-one backbone of the gilvocarcins.
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Registered trials
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.