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 condensati...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2008-01, Vol.73 (1), p.287-290
Main Authors: Jawalekar, Anup M, Meeuwenoord, Nico, Cremers, J. (Sjef) G. O, Overkleeft, Herman S, van der Marel, Gijs A, Rutjes, Floris P. J. T, van Delft, Floris L
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Carbohydrates. Nucleosides and nucleotides
Catalysis
Chemistry
Copper - chemistry
Cyclization
Exact sciences and technology
Molecular Structure
Nucleosides - chemistry
Nucleosides, nucleotides and oligonucleotides
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo702023s