ArticleAngewandte Chemie (International ed. in English)2021
Identification of a Pyrrole Intermediate Which Undergoes C-Glycosidation and Autoxidation to Yield the Final Product in Showdomycin Biosynthesis.
Article in Angewandte Chemie (International ed. in English), 2021. 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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8 citing papers in PubMed, 15 citations in OpenAlex.
- Reinvestigation of theJournal of the American Chemical Society · 2025Article
- In silico exploration of biosynthetic gene clusters in marine Streptomyces sp. and Nocardiopsis sp. from the western coast of India: Genome-based profiling using whole genome sequencing.Journal, genetic engineering & biotechnology · 2025Article
- A selective and atom-economic rearrangement of uridine by cascade biocatalysis for production of pseudouridine.Nature communications · 2023Article
- Experimental and computational snapshots of C-C bond formation in a C-nucleoside synthase.Open biology · 2023Article
- Identification of the Early Steps in Herbicidin Biosynthesis Reveals an Atypical Mechanism ofJournal of the American Chemical Society · 2022Article
- Characterization of the Oxazinomycin Biosynthetic Pathway Revealing the Key Role of a Nonheme Iron-Dependent Mono-oxygenase.Journal of the American Chemical Society · 2022Article
- Biosynthesis of C-nucleoside antibiotics in actinobacteria: recent advances and future developments.Microbial cell factories · 2022Review
- Genome mining methods to discover bioactive natural products.Natural product reports · 2021Review
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4 authors at 1 institution in 1 country.
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Abstract
Showdomycin is a C-nucleoside bearing an electrophilic maleimide base. Herein, the biosynthetic pathway of showdomycin is presented. The initial stages of the pathway involve non-ribosomal peptide synthetase (NRPS) mediated assembly of a 2-amino-1H-pyrrole-5-carboxylic acid intermediate. This intermediate is prone to air oxidation whereupon it undergoes oxidative decarboxylation to yield an imine of maleimide, which in turn yields the maleimide upon acidification. It is also shown that this pyrrole intermediate serves as the substrate for the C-glycosidase SdmA in the pathway. After coupling with ribose 5-phosphate, the resulting C-nucleoside undergoes a similar sequence of oxidation, decarboxylation and deamination to afford showdomcyin after exposure to air. These results suggest that showdomycin could be an artifact due to aerobic isolation; however, the autoxidation may also serve to convert an otherwise inert product of the biosynthetic pathway to an electrophilic C-nucleotide thereby endowing showdomycin with its observed bioactivities.
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