The synthesis and a preliminary evaluation of the pairing properties of ribo-cyclohexanyl nucleic acids (r-CNA) is herein reported. Incorporation of a single r-CNA nucleotide into natural duplexes did not enhance their stability, while a very high pairing selectivity for RNA was found. As deduced by comparative analysis of Tm and NMR data, a relationship between pairing selectivity and conformational preferences of the “sugar” moiety of r-CNA (and more generally of six-membered nucleic acids) was suggested.
Oligonucleotides containing a ribo-configured cyclohexanyl nucleoside: probing the role of sugar conformation in base pairing selectivity / Paolella, C., D'Alonzo, D., Schepers, G., Van Aerschot, A., DI FABIO, G., Palumbo, G., Herdewijn, P., Guaragna, A.. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 13:39(2015), pp. 10041-10049. [10.1039/C5OB01449B]
Oligonucleotides containing a ribo-configured cyclohexanyl nucleoside: probing the role of sugar conformation in base pairing selectivity
PAOLELLA, CONCETTA;D'ALONZO, DANIELE;DI FABIO, GIOVANNI;PALUMBO, GIOVANNI;GUARAGNA, ANNALISA
2015
Abstract
The synthesis and a preliminary evaluation of the pairing properties of ribo-cyclohexanyl nucleic acids (r-CNA) is herein reported. Incorporation of a single r-CNA nucleotide into natural duplexes did not enhance their stability, while a very high pairing selectivity for RNA was found. As deduced by comparative analysis of Tm and NMR data, a relationship between pairing selectivity and conformational preferences of the “sugar” moiety of r-CNA (and more generally of six-membered nucleic acids) was suggested.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
