Acyclic Nucleoside Phosphonates Bearing (R)- or (S)-9-[3-Hydroxy-2-(phosphonoethoxy)propyl] (HPEP) Moiety as Monomers for the Synthesis of Modified Oligonucleotides

0495572 - ÚOCHB 2019 RIV DE eng J - Článek v odborném periodiku
Kaiser, Martin Maxmilian - Novák, Pavel - Rosenbergová, Šárka - Poštová Slavětínská, Lenka - Rosenberg, Ivan - Janeba, Zlatko
Acyclic Nucleoside Phosphonates Bearing (R)- or (S)-9-[3-Hydroxy-2-(phosphonoethoxy)propyl] (HPEP) Moiety as Monomers for the Synthesis of Modified Oligonucleotides.
European Journal of Organic Chemistry. Roč. 2018, č. 37 (2018), s. 5119-5126. ISSN 1434-193X. E-ISSN 1099-0690
Institucionální podpora: RVO:61388963
Klíčová slova: nucleobases * oligonucleotides * nonamers * duplexes * hybridization * Tm values
Obor OECD: Organic chemistry
Impakt faktor: 3.029, rok: 2018

Suitably protected (R)- and (S)-HPEP {9-[3-hydroxy-2-(phosphonoethoxy)propyl]} derivatives containing adenine and thymine nucleobases were prepared as monomers for the introduction of acyclic nucleotide units into oligonucleotides. The solid phase synthesis of a series of ribo and 2-deoxyribo nonamers containing (R)-HPEP and (S)-HPEP units was successfully performed in both 5' → 3' and 3' → 5' directions. The measurement of thermal characteristics of the complexes of modified nonamers with complementary DNA and RNA strands revealed a general destabilizing effect of the introduced acyclic units on the thermal stability, but in several cases [(modif.)RNA*RNA and (modif.)DNA*RNA with (S)-HPEPA units], the duplexes were characterized in terms of Tm values.
Trvalý link: http://hdl.handle.net/11104/0288521