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. 2010 Dec 3;12(23):5486-9.
doi: 10.1021/ol102357u. Epub 2010 Nov 4.

Synthesis of oligoribonucleic acid conjugates using a cyclooctyne phosphoramidite

Pieter van Delft  1 , Nico J Meeuwenoord, Sascha Hoogendoorn, Jasper Dinkelaar, Herman S Overkleeft, Gijsbert A van der Marel, Dmitri V Filippov
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Synthesis of oligoribonucleic acid conjugates using a cyclooctyne phosphoramidite

Pieter van Delft et al. Org Lett. .

Abstract

The conjugation of a ribonucleic acid 16-mer with the cationic amphiphilic peptide penetratin and an anionic hyaluronan tetrasaccharide by means of Cu-free "click" chemistry is reported. The alkyne-functionalized 16-mer was prepared by automated solid-phase synthesis, using a newly developed strained cyclooctyne phosphoramidite in the final coupling. Cycloaddition of the alkyne functionalized RNA to the azide containing biomolecules led to a clean conversion into the corresponding nucleic acid conjugates.

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