General Principles for Yield Optimization of Nucleoside Phosphorylase-Catalyzed Transglycosylations
| العنوان: | General Principles for Yield Optimization of Nucleoside Phosphorylase-Catalyzed Transglycosylations |
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| المؤلفون: | Peter Neubauer, Katja F. Hellendahl, Robert T. Giessmann, Anke Wagner, Matthias Gimpel, Felix Kaspar |
| المصدر: | Chembiochem |
| بيانات النشر: | American Chemical Society (ACS), 2019. |
| سنة النشر: | 2019 |
| مصطلحات موضوعية: | Mathematical optimization, Work (thermodynamics), phosphates, Glycosylation, Computer science, Purine nucleoside phosphorylase, 010402 general chemistry, 01 natural sciences, Biochemistry, Modified nucleosides, Catalysis, Nucleobase, equilibrium constant, nucleoside phosphorylases, pentose-1-phosphate, Pentosyltransferases, Molecular Biology, Equilibrium constant, Phosphorolysis, 010405 organic chemistry, Chemistry, Communication, Organic Chemistry, Nucleosides, Combinatorial chemistry, Communications, 0104 chemical sciences, Yield (chemistry), Product (mathematics), Molecular Medicine, Reaction system, Nucleoside |
| الوصف: | 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. Not all nucleosides are created equal: The equilibrium constants of phosphorolysis of different nucleosides vary drastically, and so does their yield and behavior in biocatalytic transglycosylation reactions. The data, mathematical tools and guidelines presented here facilitate the reliable choice of reaction conditions for maximum yield in these reactions. |
| DOI: | 10.26434/chemrxiv.11283296 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::3a9f2845d5f6cff43a70ed5994d36add https://doi.org/10.26434/chemrxiv.11283296 |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....3a9f2845d5f6cff43a70ed5994d36add |
| قاعدة البيانات: | OpenAIRE |
| DOI: | 10.26434/chemrxiv.11283296 |
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