Synthesis of Oligoribonucleic Acid Conjugates Using a Cyclooctyne Phosphoramidite
Organic Letters2010Vol. 12(23), pp. 5486–5489
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Pieter van Delft, Nico J. Meeuwenoord, Sascha Hoogendoorn, Jasper Dinkelaar, Herman S. Overkleeft, Gijsbert A. van der Marel, Dmitri V. Filippov
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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