Synthesis and oligomerization of cysteinyl nucleosides

Nucleoside and nucleic acid analogues are known to possess a considerable therapeutic potential. In this work, by coupling cysteine to nucleosides, we successfully synthesized compounds that may not only have interesting biological properties in their monomeric form, but can be used beyond that, for...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-10, Vol.18 (4), p.8161-8178
Main Authors: Bege, Miklós, Bereczki, Ilona, Molnár, Dénes J, Kicsák, Máté, Pénzes-Daku, Krisztina, Bereczky, Zsuzsanna, Ferenc, Györgyi, Kovács, Lajos, Herczegh, Pál, Borbás, Anikó
Format: Article
Language:English
Subjects:
Acids
Adenosine
Biological properties
Coupling (molecular)
Monomers
Nucleic acids
Nucleoside analogs
Nucleosides
Oligomerization
Peptide nucleic acids
Peptides
Synthesis
Uridine
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Summary:Nucleoside and nucleic acid analogues are known to possess a considerable therapeutic potential. In this work, by coupling cysteine to nucleosides, we successfully synthesized compounds that may not only have interesting biological properties in their monomeric form, but can be used beyond that, for oligomerization, in order to produce new types of synthetic nucleic acids. We elaborated different strategies for the synthesis of cysteinyl nucleosides as monomers of cysteinyl nucleic acids using nucleophilic substitution or thiol-ene coupling as a synthetic tool, and utilised on two complementary nucleosides, uridine and adenosine. Dipeptidyl dinucleosides and pentameric cysteinyl uridine were prepared from the monomeric building blocks, which are the first members of a new class of peptide nucleic acids containing the entire ribofuranosyl nucleoside units bound to the peptide backbone. Cysteinyl nucleoside and homonucleoside oligomers, the first representatives of a new class of artificial nucleic acid family were prepared.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d0ob01890b