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Nucleosides, Nucleotides, and Their Derivatives, Analogs, and Oligomers

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (31 May 2021) | Viewed by 3475

Special Issue Editor


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Guest Editor
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland
Interests: nucleosides; nucleotides; oligonucleotide synthesis; chemical RNA synthesis; protecting groups; silyl protecting groups; combinatorial chemistry; epigenetic drugs; induced pluripotent stem cells (i-PSC); anticancer compounds

Special Issue Information

Dear Colleagues,

Nucleosides and nucleotides have drawn the attention of scientists for almost two centuries. The inosine nucleotide might be seen as a spectacular example of "scientific longevity" of this class of compounds, sparking the interest of researchers since its first isolation by Justus Liebig in 1847 (doi:10.1002/jlac.18470620302), with one of the latest reports (26 December 2018; doi:10.1073/pnas.1814367115) suggesting its primordial function in the development of the “RNA world”.

Nucleosides and nucleotides as components of native nucleic acids are the building blocks of chemically derived nucleic acids fragments, and form the basis of molecular tools of contemporary biology, xenobiology, and medicine, just to mention but a few, such as cloning, DNA/RNA sequencing, and diagnostics. Their use as antiviral and anticancer drugs, and nucleoside antibiotics, as well as their applications in nanotechnology, and their use in new materials development touches on some other areas of their important and perspective applications. The tremendous progress in understanding the live processes that have been achieved so far would not take place without studies on this group of molecules. This Special Issue aims to provide a forum for the dissemination of the latest information on the synthesis, isolation, properties, and applications of new nucleosides and nucleotides, as well as their analogs, oligomers, conjugates, materials, and drugs based-on, and so on.

Prof. Wojciech T. Markiewicz
Guest Editor

Manuscript Submission Information

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Keywords

  • nucleoside
  • nucleotide
  • nucleoside analog
  • nucleotide analog
  • synthesis
  • structure
  • biological activity
  • oligomers
  • protecting group
  • xenobiology
  • anticancer drug
  • antiviral nucleoside derivative
  • anticancer nucleoside analog
  • nucleoside antibiotics
  • epigenetic nucleoderived drugs
  • nanomaterial

Published Papers (1 paper)

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Research

19 pages, 5387 KiB  
Article
Tricyclic Nucleobase Analogs and Their Ribosides as Substrates and Inhibitors of Purine-Nucleoside Phosphorylases III. Aminopurine Derivatives
by Alicja Stachelska-Wierzchowska, Jacek Wierzchowski, Michał Górka, Agnieszka Bzowska, Ryszard Stolarski and Beata Wielgus-Kutrowska
Molecules 2020, 25(3), 681; https://doi.org/10.3390/molecules25030681 - 5 Feb 2020
Cited by 4 | Viewed by 2849
Abstract
Etheno-derivatives of 2-aminopurine, 2-aminopurine riboside, and 7-deazaadenosine (tubercidine) were prepared and purified using standard methods. 2-Aminopurine reacted with aqueous chloroacetaldehyde to give two products, both exhibiting substrate activity towards bacterial (E. coli) purine-nucleoside phosphorylase (PNP) in the reverse (synthetic) pathway. The [...] Read more.
Etheno-derivatives of 2-aminopurine, 2-aminopurine riboside, and 7-deazaadenosine (tubercidine) were prepared and purified using standard methods. 2-Aminopurine reacted with aqueous chloroacetaldehyde to give two products, both exhibiting substrate activity towards bacterial (E. coli) purine-nucleoside phosphorylase (PNP) in the reverse (synthetic) pathway. The major product of the chemical synthesis, identified as 1,N2-etheno-2-aminopurine, reacted slowly, while the second, minor, but highly fluorescent product, reacted rapidly. NMR analysis allowed identification of the minor product as N2,3-etheno-2-aminopurine, and its ribosylation product as N2,3-etheno-2-aminopurine-N2-β-d-riboside. Ribosylation of 1,N2-etheno-2-aminopurine led to analogous N2-β-d-riboside of this base. Both enzymatically produced ribosides were readily phosphorolysed by bacterial PNP to the respective bases. The reaction of 2-aminopurine-N9-β -d-riboside with chloroacetaldehyde gave one major product, clearly distinct from that obtained from the enzymatic synthesis, which was not a substrate for PNP. A tri-cyclic 7-deazaadenosine (tubercidine) derivative was prepared in an analogous way and shown to be an effective inhibitor of the E. coli, but not of the mammalian enzyme. Fluorescent complexes of amino-purine analogs with E. coli PNP were observed. Full article
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