Hydrophobic alkyl-linked base-modified pyrimidine and 7-deazapurine 2′-deoxyribonucleoside phosphoramidites: synthesis and application in solid-phase synthesis of modified and hypermodified oligonucleotides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F25%3A00643381" target="_blank" >RIV/61388963:_____/25:00643381 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/25:10509635
Result on the web
<a href="https://doi.org/10.1039/D5RA06147D" target="_blank" >https://doi.org/10.1039/D5RA06147D</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d5ra06147d" target="_blank" >10.1039/d5ra06147d</a>
Alternative languages
Result language
angličtina
Original language name
Hydrophobic alkyl-linked base-modified pyrimidine and 7-deazapurine 2′-deoxyribonucleoside phosphoramidites: synthesis and application in solid-phase synthesis of modified and hypermodified oligonucleotides
Original language description
A series of 2′-deoxyribonucleoside 3′-phosphoramidites bearing hydrophobic alkyl-linked modifications at nucleobases was synthesized, namely 5-phenylethyluracil, 5-pentylcytosine, 7-(indol-3-yl)ethyl-7-deazaadenine, and 7-isopentyl-7-deazaguanine derivatives. These nucleoside phosphoramidites were used for solid-phase synthesis of modified and hypermodified oligonucleotides containing up to fifteen modified nucleotides in a row. Their hybridization with complementary non-modified or modified oligonucleotides and thermal stability of the resulting DNA duplexes was studied using UV-vis denaturing experiments and CD spectroscopy. The results indicate that the partially modified hydrophobic DNA can still retain B-conformation, although with lower thermal stability. On the other hand, the hypermodified ONs containing all four modified nucleotides did not hybridize to duplexes likely due to formation of aggregates as indicated by dynamic light scattering measurement. This work expands the toolkit of chemically modified nucleotides for applications in functional nucleic acids or nucleic acid therapeutics, but also shows the scope and limitations of the use of hydrophobic nucleotides in hypermodified oligonucleotides and DNA.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GX20-00885X" target="_blank" >GX20-00885X: Novel Functionalized (Bio)polymers Based on DNA Display of Small Molecules</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
RSC Advances
ISSN
2046-2069
e-ISSN
2046-2069
Volume of the periodical
15
Issue of the periodical within the volume
56
Country of publishing house
GB - UNITED KINGDOM
Number of pages
10
Pages from-to
48556-48565
UT code for WoS article
001631965900001
EID of the result in the Scopus database
2-s2.0-105024751322