1024-99-3Relevant articles and documents
Ionic liquid mediated synthesis of 5-halouracil nucleosides: Key precursors for potential antiviral drugs
Kumar, Vineet,Malhotra, Sanjay V.
, p. 821 - 834 (2009)
Synthesis of antiviral 5-halouracil nucleosides, also used as key precursors for the synthesis of other potential antiviral drugs, has been demonstrated using ionic liquids as convenient and efficient reaction medium.
Transcription of Unnatural Fluorescent Nucleotides and their Application with Graphene Oxide for the Simple and Direct Detection of miRNA
Le, Binh Huy,Seo, Young Jun
, p. 1054 - 1057 (2018)
In this study we synthesized two differently sized fluorescent RNA nucleotides, rUthioTP and rUpyrTP, and examined their transcription ability using T7 RNA polymerase. The smaller rUthioTP could be incorporated and extended to produce a corresponding RNA sequence, but rUpyrTP could not. We then used this rUthioTP-containing fluorogenic transcription system, in conjunction with graphene oxide(GO), for the detection of miRNA 146a with high sensitivity and selectivity. This combination of a transcribed RNA product and GO is a simple in situ probing system for the detection of miRNA 146a—one that is less time consuming and more cost-effective.
Thermodynamic Reaction Control of Nucleoside Phosphorolysis
Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias
, p. 867 - 876 (2020)
Nucleoside analogs represent a class of important drugs for cancer and antiviral treatments. Nucleoside phosphorylases (NPases) catalyze the phosphorolysis of nucleosides and are widely employed for the synthesis of pentose-1-phosphates and nucleoside analogs, which are difficult to access via conventional synthetic methods. However, for the vast majority of nucleosides, it has been observed that either no or incomplete conversion of the starting materials is achieved in NPase-catalyzed reactions. For some substrates, it has been shown that these reactions are reversible equilibrium reactions that adhere to the law of mass action. In this contribution, we broadly demonstrate that nucleoside phosphorolysis is a thermodynamically controlled endothermic reaction that proceeds to a reaction equilibrium dictated by the substrate-specific equilibrium constant of phosphorolysis, irrespective of the type or amount of NPase used, as shown by several examples. Furthermore, we explored the temperature-dependency of nucleoside phosphorolysis equilibrium states and provide the apparent transformed reaction enthalpy and apparent transformed reaction entropy for 24 nucleosides, confirming that these conversions are thermodynamically controlled endothermic reactions. This data allows calculation of the Gibbs free energy and, consequently, the equilibrium constant of phosphorolysis at any given reaction temperature. Overall, our investigations revealed that pyrimidine nucleosides are generally more susceptible to phosphorolysis than purine nucleosides. The data disclosed in this work allow the accurate prediction of phosphorolysis or transglycosylation yields for a range of pyrimidine and purine nucleosides and thus serve to empower further research in the field of nucleoside biocatalysis. (Figure presented.).
Bifunctional inhibition of HIV-1 reverse transcriptase: A first step in designing a bifunctional triphosphate
Piao, Dongyuan,Basavapathruni, Aravind,Iyidogan, Pinar,Dai, Guangxiu,Hinz, Wolfgang,Ray, Adrian S.,Murakami, Eisuke,Feng, Joy Y.,You, Fei,Dutschman, Ginger E.,Austin, David J.,Parker, Kathlyn A.,Anderson, Karen S.
, p. 1511 - 1518 (2013)
The onset of resistance to approved anti-AIDS drugs by HIV necessitates the search for novel inhibitors of HIV-1 reverse transcriptase (RT). Developing single molecular agents concurrently occupying the nucleoside and nonnucleoside binding sites in RT is an intriguing idea but the proof of concept has so far been elusive. As a first step, we describe molecular modeling to guide focused chemical syntheses of conjugates having nucleoside (d4T) and nonnucleoside (TIBO) moieties tethered by a flexible polyethylene glycol (PEG) linker. A triphosphate of d4T-6PEG-TIBO conjugate was successfully synthesized that is recognized as a substrate by HIV-1 RT and incorporated into a double-stranded DNA.
Effective Synthesis of 5-Iodo Derivatives of Pyrimidine Morpholino Nucleosides
Vohtancev, Ivan P.,Sherstyuk, Yuliya V.,Silnikov, Vladimir N.,Abramova, Tatyana V.
, p. 332 - 342 (2018)
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Use of nucleoside phosphorylases for the preparation of 5-modified pyrimidine ribonucleosides
Alexeev, Cyril S.,Drenichev, Mikhail S.,Dorinova, Evgeniya O.,Esipov, Roman S.,Kulikova, Irina V.,Mikhailov, Sergey N.
, (2020)
Enzymatic transglycosylation, a transfer of the carbohydrate moiety from one heterocyclic base to another, is catalyzed by nucleoside phosphorylases (NPs) and is being actively developed and applied for the synthesis of biologically important nucleosides. Here, we report an efficient one-step synthesis of 5-substitited pyrimidine ribonucleosides starting from 7-methylguanosine hydroiodide in the presence of nucleoside phosphorylases (NPs).
