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. 2008 Jan 4;73(1):287-90.
doi: 10.1021/jo702023s. Epub 2007 Dec 4.

Conjugation of nucleosides and oligonucleotides by [3+2] cycloaddition

Anup M Jawalekar  1 , Nico Meeuwenoord, J Sjef G O Cremers, Herman S Overkleeft, Gijs A van der Marel, Floris P J T Rutjes, Floris L van Delft
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Conjugation of nucleosides and oligonucleotides by [3+2] cycloaddition

Anup M Jawalekar et al. J Org Chem. .

Abstract

A procedure is presented for copper(I)-catalyzed [3+2] cycloaddition of nucleosides and nucleotides in near-quantitative yield. Azido-alkyne cycloaddition was applied for the preparation of a range of adenosine dimers and derivatives with versatile functionality, as well as for the smooth condensation of two oligonucleotide strands. The described technology may find valuable application in the synthesis of oligonucleotide dimers and conjugates.

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