RNAs Containing Carbocyclic Ribonucleotides

Autor: Akabane-Nakata, Masaaki, Chickering, Tyler, Harp, Joel M., Schlegel, Mark K., Matsuda, Shigeo, Egli, Martin, Manoharan, Muthiah
Zdroj: Organic Letters; January 2022, Vol. 24 Issue: 2 p525-530, 6p
Abstrakt: Toward the goal of evaluation of carbocyclic ribonucleoside-containing oligonucleotide therapeutics, we developed convenient, scalable syntheses of all four carbocyclic ribonucleotide phosphoramidites and the uridine solid-support building block. Crystallographic analysis confirmed configuration and stereochemistry of these building blocks. Duplexes with carbocyclic RNA (car-RNA) modifications in one strand were less thermodynamically stable than duplexes with unmodified RNA. However, circular dichroism spectroscopy indicated that global conformations of the duplexes containing car-RNAs were similar to those in the unmodified duplexes.
Databáze: Supplemental Index