Solid-Supported 2 '-O-Glycoconjugation of Oligonucleotides by Azidation and Click Reactions



: Anu Kiviniemi, Pasi Virta, Mikhail S Drenichev, Sergey N Mikhailov, Harri Lönnberg

Publisher: AMER CHEMICAL SOC

: 2011

: Bioconjugate Chemistry

: BIOCONJUGATE CHEMISTRY

: BIOCONJUGATE CHEM

: 22

: 6

: 1249

: 1255

: 7

: 1043-1802

DOI: https://doi.org/10.1021/bc200097g(external)


2'-O-[(2-Bromoethoxy)methyl]cytidine and 2'-O-[(2-azidoethoxy)methyl]cytidine have been prepared and introduced as appropriately protected 3'-phosphoramidite (1) and 3'-(H-phosphonate) (2) building blocks, respectively, into 2'-O-methyl oligoribonucleotides. The support-bound oligonucleotides were subjected to two consecutive conjugations with alkynyl-functionalized monosaccharides. The first saccharide was introduced by a Cu(I) promoted click reaction with 2 and the second by azidation of the 2-bromoethoxy group of 1 followed by the click reaction. The influence of the 2'-glycoconjugations on hybridization with DNA and 2'-O-methyl RNA targets was studied. Two saccharide units within a 15-mer oligonucleotide had a barely noticeable effect on the duplex stability, while introduction of a third one moderately decreased the melting temperature.



Last updated on 2024-26-11 at 22:57