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Molecules 2013, 18(7), 7346-7363; doi:10.3390/molecules18077346
Article

Oligonucleotide Tagging for Copper-Free Click Conjugation

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1 Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands 2 SynAffix BV, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands 3 Berry and Associates, Inc., 2434 Bishop Circle East, Dexter, MI 48130, USA
* Author to whom correspondence should be addressed.
Received: 19 April 2013 / Revised: 24 May 2013 / Accepted: 5 June 2013 / Published: 24 June 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

Copper-free click chemistry between cyclooctynes and azide is a mild, fast and selective technology for conjugation of oligonucleotides. However, technology for site-specific introduction of the requisite probes by automated protocols is scarce, while the reported cyclooctynes are large and hydrophobic. In this work, it is demonstrated that the introduction of bicyclo[6.1.0]nonyne (BCN) into synthetic oligonucleotides is feasible by standard solid-phase phosphoramidite chemistry. A range of phosphoramidite building blocks is presented for incoporation of BCN or azide, either on-support or in solution. The usefulness of the approach is demonstrated by the straightforward and high-yielding conjugation of the resulting oligonucleotides, including biotinylation, fluorescent labeling, dimerization and attachment to polymer.
Keywords: copper-free click; oligonucleotide conjugation; bicyclononyne; azide; strain-promoted cycloaddition copper-free click; oligonucleotide conjugation; bicyclononyne; azide; strain-promoted cycloaddition
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Jawalekar, A.M.; Malik, S.; Verkade, J.M.M.; Gibson, B.; Barta, N.S.; Hodges, J.C.; Rowan, A.; van Delft, F.L. Oligonucleotide Tagging for Copper-Free Click Conjugation. Molecules 2013, 18, 7346-7363.

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