2'-Hydrazine oligonucleotides: synthesis and efficient conjugation with aldehydes.

Abstract

Oligodeoxyribonucleotides that contain a novel nucleoside, 2'-O-(2-hydrazinoethyl)uridine, were synthesized by sodium cyanoborohydride reduction of hydrazones formed from 2'-aldehyde oligonucleotides and FmocNHNH2 followed by ammonia deprotection. 2'-Hydrazine oligonucleotides were used successfully to obtain a series of conjugates with various aldehydes by hydrazone formation. The method was shown to be suitable for the preparation of oligonucleotide-peptide conjugates.