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Conjugation of nucleosides and oligonucleotides by [3+2] cycloaddition. 2008
Anup M Jawalekar, and
Nico Meeuwenoord, and
J Sjef G O Cremers, and
Herman S Overkleeft, and
Gijs A van der Marel, and
Floris P J T Rutjes, and
Floris L van Delft
Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.
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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