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Arylethynyl- or Alkynyl-Linked Pyrimidine and 7-Deazapurine 2′-Deoxyribonucleoside 3′-Phosphoramidites for Chemical Synthesis of Hypermodified Hydrophobic Oligonucleotides
- 1.0576504 - ÚOCHB 2024 RIV US eng J - Journal Article
Jestřábová, Ivana - Poštová Slavětínská, Lenka - Hocek, Michal
Arylethynyl- or Alkynyl-Linked Pyrimidine and 7-Deazapurine 2′-Deoxyribonucleoside 3′-Phosphoramidites for Chemical Synthesis of Hypermodified Hydrophobic Oligonucleotides.
ACS Omega. Roč. 8, č. 42 (2023), s. 39447-39453. ISSN 2470-1343. E-ISSN 2470-1343
R&D Projects: GA ČR(CZ) GX20-00885X
Institutional support: RVO:61388963
Keywords : gene inhibition * DNA * oligodeoxynucleotides
OECD category: Organic chemistry
Impact factor: 3.7, year: 2023
Method of publishing: Open access
https://doi.org/10.1021/acsomega.3c05202
We 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.
Permanent Link: https://hdl.handle.net/11104/0346062
Number of the records: 1