New phosphoramidite derivatives for the preparation of oligonucleotides containing a hydrazide group in any specified position of the oligonucleotide chain

Abstract

A new versatile method for the preparation of oligonucleotides containing hydrazide groups in any position of the oligonucleotide chain by standard phosphoramidite automated oligo nucleotide synthesis is proposed. The method is based on the use of a series of new modified components for oligonucleotide synthesis. An original protecting group for the hydrazide group is proposed. The presence of the hydrazide group in the obtained oligonucleotides and its high reactivity were demonstrated by the reaction with 4 methoxybenzaldehyde in solution.

Chemical Syntheses of 3′ and 5′ Phosphorylated Oligonucleotides: An Overview

“…In addition to their use in phosphorylation reactions, malonatebased phosphoramidite reagents have also been used for the masking of internucleotidic phosphodiester [190][191][192][193], as protecting groups of the hydrazide function before its introduction into ONs [194] or to obtain polyfunctionalized bioconjugates (by the use of derivatives 166) [195,196].…”

Chemical Syntheses of 3′ and 5′ Phosphorylated Oligonucleotides: An Overview

“…In addition to their use in phosphorylation reactions, malonatebased phosphoramidite reagents have also been used for the masking of internucleotidic phosphodiester [190][191][192][193], as protecting groups of the hydrazide function before its introduction into ONs [194] or to obtain polyfunctionalized bioconjugates (by the use of derivatives 166) [195,196].…”

Chemical Syntheses of 3′ and 5′ Phosphorylated Oligonucleotides: An Overview

“…In addition to their use in phosphorylation reactions, malonatebased phosphoramidite reagents have also been used for the masking of internucleotidic phosphodiester [190][191][192][193], as protecting groups of the hydrazide function before its introduction into ONs [194] or to obtain polyfunctionalized bioconjugates (by the use of derivatives 166) [195,196].…”

Chemical Syntheses of 3′ and 5′ Phosphorylated Oligonucleotides: An Overview

“…In addition to their use in phosphorylation reactions, malonatebased phosphoramidite reagents have also been used for the masking of internucleotidic phosphodiester [190][191][192][193], as protecting groups of the hydrazide function before its introduction into ONs [194] or to obtain polyfunctionalized bioconjugates (by the use of derivatives 166) [195,196].…”