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Updated: May 29, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
DNA or RNA oligonucleotide 2'-hydrazides for chemoselective click-type ligation with carbonyl compounds
Elena A Khomyakova1, Eugeny M Zubin, Igor P Smirnov
1Department of Chemistry, A. N. Belozersky Institute of Physico-Chemical Biology, M. V. Lomonossov Moscow State University, Leninskie Gory, Moscow, Russia.
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.
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