ArticleChembiochem : a European journal of chemical biology2020
General Principles for Yield Optimization of Nucleoside Phosphorylase-Catalyzed Transglycosylations.
Article in Chembiochem : a European journal of chemical biology, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Nucleoside Phosphorylases make N7-xanthosine.Nature communications · 2024Article
- A selective and atom-economic rearrangement of uridine by cascade biocatalysis for production of pseudouridine.Nature communications · 2023Article
- Optimized Biocatalytic Synthesis of 2-Selenopyrimidine Nucleosides by Transglycosylation*.Chembiochem : a European journal of chemical biology · 2021Article
- The Peculiar Case of the Hyper-thermostable Pyrimidine Nucleoside Phosphorylase from Thermus thermophilus*.Chembiochem : a European journal of chemical biology · 2021Article
- Kinetic Analysis of the Hydrolysis of Pentose-1-phosphates through Apparent Nucleoside Phosphorolysis Equilibrium Shifts*.Chemphyschem : a European journal of chemical physics and physical chemistry · 2021Article
- Reverse C-glycosidase reaction provides C-nucleotide building blocks of xenobiotic nucleic acids.Nature communications · 2020Article
- Spectral Unmixing-Based Reaction Monitoring of Transformations between Nucleosides and Nucleobases.Chembiochem : a European journal of chemical biology · 2020Article
- General Principles for Yield Optimization of Nucleoside Phosphorylase-Catalyzed Transglycosylations.Chembiochem : a European journal of chemical biology · 2020Article
- Efficient Biocatalytic Synthesis of Dihalogenated Purine Nucleoside Analogues Applying Thermodynamic Calculations.Molecules (Basel, Switzerland) · 2020Article
- Modular Enzymatic Cascade Synthesis of Nucleotides Using a (d)ATP Regeneration System.Frontiers in bioengineering and biotechnology · 2020Article
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6 authors.
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Abstract
The biocatalytic synthesis of natural and modified nucleosides with nucleoside phosphorylases offers the protecting-group-free direct glycosylation of free nucleobases in transglycosylation reactions. This contribution presents guiding principles for nucleoside phosphorylase-mediated transglycosylations alongside mathematical tools for straightforward yield optimization. We illustrate how product yields in these reactions can easily be estimated and optimized using the equilibrium constants of phosphorolysis of the nucleosides involved. Furthermore, the varying negative effects of phosphate on transglycosylation yields are demonstrated theoretically and experimentally with several examples. Practical considerations for these reactions from a synthetic perspective are presented, as well as freely available tools that serve to facilitate a reliable choice of reaction conditions to achieve maximum product yields in nucleoside transglycosylation reactions.
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