1. Synthesis and oligomerization of cysteinyl nucleosides
- Author
-
Miklós Bege, Krisztina Pénzes-Daku, Anikó Borbás, Györgyi Ferenc, Dénes Molnár, Máté Kicsák, Lajos Kovács, Pál Herczegh, Ilona Bereczki, and Zsuzsanna Bereczky
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Peptide ,Nucleosides ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Uridine ,0104 chemical sciences ,chemistry.chemical_compound ,Monomer ,chemistry ,Nucleophilic substitution ,Nucleic acid ,Physical and Theoretical Chemistry ,Nucleoside ,Nucleic acid analogue ,Cysteine - Abstract
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.
- Published
- 2020