ArticleChembiochem : a European journal of chemical biology2009
Inactivation of the ketoreductase gilU gene of the gilvocarcin biosynthetic gene cluster yields new analogues with partly improved biological activity.
Article in Chembiochem : a European journal of chemical biology, 2009. 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.
- Bioactive Angucyclines/Angucyclinones Discovered from 1965 to 2023.Marine drugs · 2025Review
- Ravidomycin Analogs fromJournal of natural products · 2023Article
- Engineering BioBricks for Deoxysugar Biosynthesis and Generation of New Tetracenomycins.ACS omega · 2023Article
- The functional differentiation of the post-PKS tailoring oxygenases contributed to the chemical diversities of atypical angucyclines.Synthetic and systems biotechnology · 2018Review
- A comprehensive review of glycosylated bacterial natural products.Chemical Society reviews · 2015Review
- Enzymatic methylation and structure-activity-relationship studies on polycarcin V, a gilvocarcin-type antitumor agent.Chembiochem : a European journal of chemical biology · 2014Article
- Delineation of gilvocarcin, jadomycin, and landomycin pathways through combinatorial biosynthetic enzymology.Current opinion in chemical biology · 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
- Characterization of the TDP-D-ravidosamine biosynthetic pathway: one-pot enzymatic synthesis of TDP-D-ravidosamine from thymidine-5-phosphate and glucose-1-phosphate.Organic & biomolecular chemistry · 2011Article
- Engineered biosynthesis of gilvocarcin analogues with altered deoxyhexopyranose moieties.Applied and environmental microbiology · 2011Article
- Cloning and characterization of the ravidomycin and chrysomycin biosynthetic gene clusters.Chembiochem : a European journal of chemical biology · 2010Article
- GilR, an unusual lactone-forming enzyme involved in gilvocarcin biosynthesis.Chembiochem : a European journal of chemical biology · 2009Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Four new analogues of the gilvocarcin-type aryl-C-glycoside antitumor compounds, namely 4'-hydroxy gilvocarcin V (4'-OH-GV), 4'-hydroxy gilvocarcin M, 4'-hydroxy gilvocarcin E and 12-demethyl-defucogilvocarcin V, were produced through inactivation of the gilU gene. The 4'-OH-analogues showed improved activity against lung cancer cell lines as compared to their parent compounds without 4'-OH group (gilvocarcins V and E). The structures of the sugar-containing new mutant products indicate that the enzyme GilU acts as an unusual ketoreductase involved in the biosynthesis of the C-glycosidically linked deoxysugar moiety of the gilvocarcins. The structures of the new gilvocarcins indicate substrate flexibility of the post-polyketide synthase modifying enzymes, particularly the C-glycosyltransferase and the enzyme responsible for the sugar ring contraction. The results also shed light into biosynthetic sequence of events in the late steps of biosynthetic pathway of gilvocarcin V.
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