ArticleNature communications2020
Reverse C-glycosidase reaction provides C-nucleotide building blocks of xenobiotic nucleic acids.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Enzymatic synthesis of key RNA therapeutic building blocks using simple phosphate donors.Nature communications · 2025Article
- A combined pseudouridine biomanufacturing platform enabled by a streamlined designer pathway.Nature communications · 2025Article
- N- to C-Glycoside Rearrangement of Uridine 5'-Phosphate in Two Enzymatic Steps for the Production of Pseudouridine 5'-Phosphate.Biotechnology and bioengineering · 2025Article
- Integrated Chemoenzymatic Synthesis of the mRNA Vaccine Building Block NAngewandte Chemie (International ed. in English) · 2025Article
- Reinvestigation of theJournal of the American Chemical Society · 2025Article
- Structure and function of the pseudouridine 5'-monophosphate glycosylase PUMY fromRNA biology · 2024Article
- Metabolic Engineering ofACS omega · 2023Article
- A selective and atom-economic rearrangement of uridine by cascade biocatalysis for production of pseudouridine.Nature communications · 2023Article
- 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
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2 authors.
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Abstract
C-Analogues of the canonical N-nucleosides have considerable importance in medicinal chemistry and are promising building blocks of xenobiotic nucleic acids (XNA) in synthetic biology. Although well established for synthesis of N-nucleosides, biocatalytic methods are lacking in C-nucleoside synthetic chemistry. Here, we identify pseudouridine monophosphate C-glycosidase for selective 5-β-C-glycosylation of uracil and derivatives thereof from pentose 5-phosphate (D-ribose, 2-deoxy-D-ribose, D-arabinose, D-xylose) substrates. Substrate requirements of the enzymatic reaction are consistent with a Mannich-like addition between the pyrimidine nucleobase and the iminium intermediate of enzyme (Lys166) and open-chain pentose 5-phosphate. β-Elimination of the lysine and stereoselective ring closure give the product. We demonstrate phosphorylation-glycosylation cascade reactions for efficient, one-pot synthesis of C-nucleoside phosphates (yield: 33 - 94%) from unprotected sugar and nucleobase. We show incorporation of the enzymatically synthesized C-nucleotide triphosphates into nucleic acids by RNA polymerase. Collectively, these findings implement biocatalytic methodology for C-nucleotide synthesis which can facilitate XNA engineering for synthetic biology applications.
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