Conjugation of nucleosides and oligonucleotides by [3+2] cycloaddition.
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.
Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.
Anup M
AM
Jawalekar
Nico
N
Meeuwenoord
J Sjef G O
JS
Cremers
Herman S
HS
Overkleeft
Gijs A
GA
van der Marel
Floris P J T
FP
Rutjes
Floris L
FL
van Delft
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D009705:Nucleosides; D009841:Oligonucleotides; D003300:Copper