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Arylethynyl- or Alkynyl-Linked Pyrimidine and 7-Deazapurine 2′-Deoxyribonucleoside 3′-Phosphoramidites for Chemical Synthesis of Hypermodified Hydrophobic Oligonucleotides

  1. 1.
    SYSNO ASEP0576504
    Document TypeJ - Journal Article
    R&D Document TypeJournal Article
    Subsidiary JČlánek ve WOS
    TitleArylethynyl- or Alkynyl-Linked Pyrimidine and 7-Deazapurine 2′-Deoxyribonucleoside 3′-Phosphoramidites for Chemical Synthesis of Hypermodified Hydrophobic Oligonucleotides
    Author(s) Jestřábová, Ivana (UOCHB-X)
    Poštová Slavětínská, Lenka (UOCHB-X) RID
    Hocek, Michal (UOCHB-X) RID, ORCID
    Source TitleACS Omega. - : American Chemical Society - ISSN 2470-1343
    Roč. 8, č. 42 (2023), s. 39447-39453
    Number of pages7 s.
    Languageeng - English
    CountryUS - United States
    Keywordsgene inhibition ; DNA ; oligodeoxynucleotides
    OECD categoryOrganic chemistry
    R&D ProjectsGX20-00885X GA ČR - Czech Science Foundation (CSF)
    Method of publishingOpen access
    Institutional supportUOCHB-X - RVO:61388963
    UT WOS001090913900001
    EID SCOPUS85176813528
    DOI10.1021/acsomega.3c05202
    AnnotationWe designed and synthesized a set of 2′-deoxyribonucleoside 3′-phosphoramidites derived from 5-phenylethynyluracil, 5-(pentyn-1-yl)cytosine, 7-(indol-3-yl)ethynyl-7-deazaadenine, and 7-isopropylethynyl-7-deazaguanine. These nucleoside phosphoramidites were successfully used for automated solid-phase synthesis of oligonucleotides containing one or several modifications, including fully modified sequences where every nucleobase was displaying a modification, and their hybridization was studied. The phosphoramidite building blocks have potential for synthesis of hypermodified aptamers and other functional nucleic acid-based polymers, which sequence-specifically display amino acid-like hydrophobic substituents.
    WorkplaceInstitute of Organic Chemistry and Biochemistry
    Contactasep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418
    Year of Publishing2024
    Electronic addresshttps://doi.org/10.1021/acsomega.3c05202
Number of the records: 1  

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