Nucleosides, Nucleotides & Nucleic Acids 2011-01-01

DNA or RNA oligonucleotide 2'-hydrazides for chemoselective click-type ligation with carbonyl compounds.

Elena A Khomyakova, Eugeny M Zubin, Igor P Smirnov, Galina E Pozmogova, Dmitry A Stetsenko, Tatiana S Oretskaya

Index: Nucleosides Nucleotides Nucleic Acids 30(7-8) , 577-84, (2011)

Full Text: HTML

Abstract

An efficient method for the synthesis of DNA or RNA oligonucleotide 2'-hydrazides is described. Fully deprotected oligonucleotides containing a hydrazide group at the 2'-position of a uridine residue were obtained by a novel two-step procedure: periodate cleavage of an oligonucleotide with 1,2-diol group followed by conversion of the aldehyde to hydrazide with an extended linker arm using a homobifunctional reagent succinic dihydrazide and NaBH(3)CN. The resulting oligonucleotide 2'-hydrazides were efficiently conjugated by a click-type reaction at acidic pH to aliphatic or aromatic aldehydes with or without NaBH(3)CN reduction to afford novel 2'-conjugates.