Synthesis of oligoribonucleic acid conjugates using a cyclooctyne phosphoramidite.
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.
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Pieter
P
van Delft
Nico J
NJ
Meeuwenoord
Sascha
S
Hoogendoorn
Jasper
J
Dinkelaar
Herman S
HS
Overkleeft
Gijsbert A
GA
van der Marel
Dmitri V
DV
Filippov
D034242:Cyclooctanes / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012313:RNA / Q000138:chemical synthesis*
D034242:Cyclooctanes; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D012313:RNA; C474479:cyclooctane