Improved Metal-Free Approach for the Synthesis of Protected Thiol Containing Thymidine Nucleoside Phosphoramidite and Its Application for the Synthesis of Ligatable Oligonucleotide Conjugates

Oligonucleotide conjugates are versatile scaffolds that can be applied in DNA-based screening platforms and ligand display or as therapeutics. Several different chemical approaches are available for functionalizing oligonucleotides, which are often carried out on the 5′ or 3′ end. Modifying oligonuc...

Teljes leírás

Elmentve itt :
Bibliográfiai részletek
Szerzők: Kupihár Zoltán
Ferenc Györgyi
Petrovicz Vencel László
Fáy Viktória R.
Kovács Lajos
Martinek Tamás
Hegedüs Zsófia
Dokumentumtípus: Cikk
Megjelent: 2023
Sorozat:PHARMACEUTICS 15 No. 1
Tárgyszavak:
doi:10.3390/pharmaceutics15010248

mtmt:33597958
Online Access:http://publicatio.bibl.u-szeged.hu/28481
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245 1 0 |a Improved Metal-Free Approach for the Synthesis of Protected Thiol Containing Thymidine Nucleoside Phosphoramidite and Its Application for the Synthesis of Ligatable Oligonucleotide Conjugates  |h [elektronikus dokumentum] /  |c  Kupihár Zoltán 
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520 3 |a Oligonucleotide conjugates are versatile scaffolds that can be applied in DNA-based screening platforms and ligand display or as therapeutics. Several different chemical approaches are available for functionalizing oligonucleotides, which are often carried out on the 5′ or 3′ end. Modifying oligonucleotides in the middle of the sequence opens the possibility to ligate the conjugates and create DNA strands bearing multiple different ligands. Our goal was to establish a complete workflow that can be applied for such purposes from monomer synthesis to templated ligation. To achieve this, a monomer is required with an orthogonal functional group that can be incorporated internally into the oligonucleotide sequence. This is followed by conjugation with different molecules and ligation with the help of a complementary template. Here, we show the synthesis and the application of a thiol-modified thymidine nucleoside phosphoramidite to prepare ligatable oligonucleotide conjugates. The conjugations were performed both in solution and on solid phase, resulting in conjugates that can be assembled into multivalent oligonucleotides decorated with tissue-targeting peptides using templated ligation. 
650 4 |a Kémiai tudományok 
650 4 |a Általános orvostudomány 
700 0 1 |a Ferenc Györgyi  |e aut 
700 0 1 |a Petrovicz Vencel László  |e aut 
700 0 1 |a Fáy Viktória R.  |e aut 
700 0 1 |a Kovács Lajos  |e aut 
700 0 1 |a Martinek Tamás  |e aut 
700 0 1 |a Hegedüs Zsófia  |e aut 
856 4 0 |u http://publicatio.bibl.u-szeged.hu/28481/1/pharmaceutics-15-00248.pdf  |z Dokumentum-elérés