ArticleAngewandte Chemie (International ed. in English)2019
Identification of the C-Glycoside Synthases during Biosynthesis of the Pyrazole-C-Nucleosides Formycin and Pyrazofurin.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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18 citing papers in PubMed, 43 citations in OpenAlex.
- Pyrazofurin Biosynthesis Involves Nonenzymatic Ring Contraction of a Pyridazine Intermediate Triggered by a Rieske Enzyme-Catalyzed Oxygenation.Journal of the American Chemical Society · 2025Article
- Identification of a l-Threonine-Utilizing Hydrazine Synthetase for Thrazarine Biosynthesis in Streptomyces coerulescens MH802-fF5.Chembiochem : a European journal of chemical biology · 2025Article
- Reinvestigation of theJournal of the American Chemical Society · 2025Article
- Revision of the Formycin A and Pyrazofurin Biosynthetic Pathways Reveals Specificity for d-Glutamic Acid and a CrypticJournal of the American Chemical Society · 2025Article
- Synthesis ofACS omega · 2024Article
- Purine nucleoside antibiotics: recent synthetic advances harnessing chemistry and biology.Natural product reports · 2024Review
- Reconstitution of the Final Steps in the Biosynthesis of Valanimycin Reveals the Origin of Its Characteristic Azoxy Moiety.Angewandte Chemie (International ed. in English) · 2024Article
- Pseudouridine-Modifying Enzymes SapB and SapH Control Entry into the Pseudouridimycin Biosynthetic Pathway.ACS chemical biology · 2023Article
- 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
- Identification of a Pyrrole Intermediate Which Undergoes C-Glycosidation and Autoxidation to Yield the Final Product in Showdomycin Biosynthesis.Angewandte Chemie (International ed. in English) · 2021Article
- Advances in RNA Epigenetic Modifications in Hepatocellular Carcinoma and Potential Targeted Intervention Strategies.Frontiers in cell and developmental biology · 2021Review
- Reverse C-glycosidase reaction provides C-nucleotide building blocks of xenobiotic nucleic acids.Nature communications · 2020Article
- Uncovering the chemistry of C-C bond formation in C-nucleoside biosynthesis: crystal structure of a C-glycoside synthase/PRPP complex.Chemical communications (Cambridge, England) · 2020Article
- Whole-Genome Sequence ofMicrobiology resource announcements · 2020Article
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Authors and funding
6 authors at 1 institution in 2 countries.
Funding
Abstract
C-Nucleosides are characterized by a C-C rather than a C-N linkage between the heterocyclic base and the ribofuranose ring. While the biosynthesis of pseudouridine-C-nucleosides has been studied, less is known about the pyrazole-C-nucleosides such as the formycins and pyrazofurin. Herein, genome screening of Streptomyces candidus NRRL 3601 led to the discovery of the pyrazofurin biosynthetic gene cluster pyf. In vitro characterization of gene product PyfQ demonstrated that it is able to catalyze formation of the C-glycoside carboxyhydroxypyrazole ribonucleotide (CHPR) from 4-hydroxy-1H-pyrazole-3,5-dicarboxylic acid and phosphoribosyl pyrophosphate (PRPP). Similarly, ForT, the PyfQ homologue in the formycin pathway, can catalyze the coupling of 4-amino-1H-pyrazole-3,5-dicarboxylic acid and PRPP to form carboxyaminopyrazole ribonucleotide. Finally, PyfP and PyfT are shown to catalyze amidation of CHPR to pyrazofurin 5'-phosphate thereby establishing the latter stages of both pyrazofurin and formycin biosynthesis.
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