ArticleOrganic & biomolecular chemistry2016
A biocatalytic approach to capuramycin analogues by exploiting a substrate permissive N-transacylase CapW.
Article in Organic & biomolecular chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Development of the Esterase PestE for Amide Bond Synthesis Under Aqueous Conditions: Enzyme Cascades for Converting Waste PET into Tamibarotene.Angewandte Chemie (International ed. in English) · 2025Article
- Biocatalytic Heteroaromatic Amide Formation in Water Enabled by a Catalytic Tetrad and Two Access Tunnels.ACS catalysis · 2024Article
- Identification and characterization of enzymes involved in the biosynthesis of pyrimidine nucleoside antibiotics.Natural product reports · 2021Review
- Pd-catalyzed stereoselective tandem ring-opening amination/cyclization of vinyl γ-lactones: access to caprolactam diversity.Chemical science · 2020Article
- Looking beyond Typical Treatments for Atypical Mycobacteria.Antibiotics (Basel, Switzerland) · 2020Review
- Mechanism of action of nucleoside antibacterial natural product antibiotics.The Journal of antibiotics · 2019Review
- Biosynthetic and Synthetic Strategies for Assembling Capuramycin-Type Antituberculosis Antibiotics.Molecules (Basel, Switzerland) · 2019Review
- Nature's combinatorial biosynthesis and recently engineered production of nucleoside antibiotics in Streptomyces.World journal of microbiology & biotechnology · 2017Review
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Authors and funding
11 authors.
Funding
Abstract
Using the ATP-independent transacylase CapW required for the biosynthesis of capuramycin-type antibiotics, we developed a biocatalytic approach for the synthesis of 43 analogues via a one-step aminolysis reaction from a methyl ester precursor as an acyl donor and various nonnative amines as acyl acceptors. Further examination of the donor substrate scope for CapW revealed that this enzyme can also catalyze a direct transamidation reaction using the major capuramycin congener as a semisynthetic precursor. Biological activity tests revealed that a few of the new capuramycin analogues have significantly improved antibiotic activity against Mycobacterium smegmatis MC2 155 and Mycobacterium tuberculosis H37Rv. Furthermore, most of the analogues are able to be covalently modified by the phosphotransferase CapP/Cpr17 involved in self resistance, providing critical insight for future studies regarding clinical development of the capuramycin antimycobacterial antibiotics.
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