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.
Jawalekar
Anup M
AM
Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.
Meeuwenoord
Nico
N
Cremers
J Sjef G O
JS
Overkleeft
Herman S
HS
van der Marel
Gijs A
GA
Rutjes
Floris P J T
FP
van Delft
Floris L
FL
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