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Molecules
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Nucleoside and Nucleotide Analogues: Chemical Synthesis and Applications
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Nucleoside and Nucleotide Analogues: Chemical Synthesis and Applications

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

Deadline for manuscript submissions: 31 December 2024 | Viewed by 1427

Special Issue Editors

Dr. Satu Mikkola

E-Mail Website
Guest Editor
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland
Interests: nucleic acids; phosphodiesters; reaction mechanisms; catalysis
Prof. Dr. Pasi Virta

E-Mail Website
Guest Editor
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland
Interests: nucleic acids; oligonucleotides and their conjugates; nucleic acid-based nanoparticles; liquid phase oligonucleotide synthesis
Dr. Tuomas Lönnberg

E-Mail Website
Guest Editor
Department of Chemistry, University of Turku, FIN-20014 Turku, Finland
Interests: organometallic nucleoside analogues; metal-mediated base pairing; base filling; RNA cleavage
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Nucleoside and nucleotide analogs have been intensively studied over the last decades. They have found various applications in chemical and biochemical research, and medicine. The development of nucleoside-based antivirals and pro-drugs started with the AIDS epidemic, and their importance was further emphasized by the recent COVID-19 pandemic. Currently, the majority of research on nucleoside and nucleotide analogs describe the synthesis of potential antiviral agents, with SARS-CoV being the prevailing target.

The applications of nucleoside and nucleotide analogs are, however, much more diverse. Mechanistic studies with analogues are used to obtain information on basic reaction mechanisms and interactions of nucleic acids. A more recent application is the use of fluorescent analogues in detection technology.

While we do not want to exclude any approach in this Special Issue on nucleoside and nucleotide analogs, we would like to concentrate on chemical applications, such as studies on reaction mechanisms, interactions, recognition, and development of detection methods, as well as novel synthetic methods. 

Dr. Satu Mikkola
Prof. Dr. Pasi Virta
Dr. Tuomas Lönnberg
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • nucleoside analogues
  • nucleic acids
  • interactions
  • detection
  • synthesis
  • reaction mechanism

Published Papers (2 papers)

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Research

26 pages, 7873 KiB  
Article
Synthesis of 4′-Thionucleoside Analogues Bearing a C2′ Stereogenic All-Carbon Quaternary Center
by Carla Eymard, Amarender Manchoju, Abir Almazloum, Starr Dostie, Michel Prévost, Mona Nemer and Yvan Guindon
Molecules 2024, 29(7), 1647; https://doi.org/10.3390/molecules29071647 - 06 Apr 2024
Viewed by 512
Abstract
The design of novel 4′-thionucleoside analogues bearing a C2′ stereogenic all-carbon quaternary center is described. The synthesis involves a highly diastereoselective Mukaiyama aldol reaction, and a diastereoselective radical-based vinyl group transfer to generate the all-carbon stereogenic C2′ center, along with different approaches to [...] Read more.
The design of novel 4′-thionucleoside analogues bearing a C2′ stereogenic all-carbon quaternary center is described. The synthesis involves a highly diastereoselective Mukaiyama aldol reaction, and a diastereoselective radical-based vinyl group transfer to generate the all-carbon stereogenic C2′ center, along with different approaches to control the selectivity of the N-glycosidic bond. Intramolecular SN2-like cyclization of a mixture of acyclic thioaminals provided analogues with a pyrimidine nucleobase. A kinetic bias favoring cyclization of the 1′,2′-anti thioaminal furnished the desired β-D-4′-thionucleoside analogue in a 7:1 ratio. DFT calculations suggest that this kinetic resolution originates from additional steric clash in the SN2-like transition state for 1′,4′-trans isomers, causing a significant decrease in their reaction rate relative to 1′,4′-cis counterparts. N-glycosylation of cyclic glycosyl donors with a purine nucleobase enabled the formation of novel 2-chloroadenine 4′-thionucleoside analogues. These proprietary molecules and other derivatives are currently being evaluated both in vitro and in vivo to establish their biological profiles. Full article
(This article belongs to the Special Issue Nucleoside and Nucleotide Analogues: Chemical Synthesis and Applications)
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19 pages, 2630 KiB  
Article
1H-1,2,3-triazolyl-1,6-naphthyridin-7(6H)-ones as Potential Fluorescent Nucleoside Analogues: Synthesis and Optical Properties
by Anissa Beghennou, Océane Rondot, Vincent Corcé and Candice Botuha
Molecules 2024, 29(3), 687; https://doi.org/10.3390/molecules29030687 - 01 Feb 2024
Viewed by 612
Abstract
In this article, we present the synthesis and the optical properties of three original molecules as potential fluorescent ribonucleoside analogues incorporating a 1,6-naphthyridin-7(6H)-one scaffold as a fluorescent nucleobase and a 1,2,3-triazole as a linkage. The nucleosides were prepared via a Cu [...] Read more.
In this article, we present the synthesis and the optical properties of three original molecules as potential fluorescent ribonucleoside analogues incorporating a 1,6-naphthyridin-7(6H)-one scaffold as a fluorescent nucleobase and a 1,2,3-triazole as a linkage. The nucleosides were prepared via a Cu alkyne-azide cycloaddition (CuAAC) reaction between a ribofuranosyl azide and a 4-ethynylpyridine partner. Construction of substituted 1,6-naphthyridin-7(6H)-ones was achieved through two additional steps. Optical property studies were investigated on nucleoside analogues. Powerful fluorescence properties have been evidenced with a remarkable change of emissivity depending on the polarity of the solvent, making these molecules suitable as a new class of artificial fluorescent nucleosides for investigating enzyme binding sites as well as probing nucleic acids. In addition, we are convinced that such analogues could be of great interest in the search for new antiviral or antitumoral drugs based on nucleosides. Full article
(This article belongs to the Special Issue Nucleoside and Nucleotide Analogues: Chemical Synthesis and Applications)
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