Unit

UNIT 4.50 Preparation of Azido Containing Oligonucleotides Through Diazo Transfer Reaction

  1. Rémy Lartia,
  2. Laureen Bonnat,
  3. Pierre Murat,
  4. Eric Defrancq

Published Online: 1 SEP 2012

DOI: 10.1002/0471142700.nc0450s50

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Lartia, R., Bonnat, L., Murat, P. and Defrancq, E. 2012. Preparation of Azido Containing Oligonucleotides Through Diazo Transfer Reaction. Current Protocols in Nucleic Acid Chemistry. 50:4.50:4.50.1–4.50.7.

Author Information

  1. Département de Chimie Moléculaire, Université Joseph Fourier, Grenoble, France

Publication History

  1. Published Online: 1 SEP 2012

Abstract

The use of diazo transfer reagent, imidazole-1-sulfonyl azide hydrochloride (ISAHC), in the presence of Cu2+ cation enables clean and efficient conversion of aminated oligodeoxyribonucleotides (ODNs) into their azido counterparts under mild conditions. ODNs bearing amino tether either at the 3′, 5′, or any internal position could be modified in this way, thus demonstrating the versatility of this reaction. The method also benefits from the commercial availability or easy access by routine automated DNA synthesis of amino-containing oligodeoxyribonucleotide starting material. Easy access to such azido-modified ODNs is of great interest for conjugation in particular through copper catalyzed 1,3-dipolar cycloaddition (CuAAC reaction). Curr. Protoc. Nucleic Acid Chem. 50:4.50.1-4.50.7. © 2012 by John Wiley & Sons, Inc.

Keywords:

  • azide;
  • click-chemistry;
  • conjugation;
  • diazotransfer reaction;
  • Huisgen reaction;
  • Staudinger reaction