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This article was published as part of the
Applications of click chemistry themed
issue
Guest editors Professors . Finn and Valery Fokin
Please take a look at the issue 4 table of contents to access
other reviews in this themed issue
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CRITICAL REVIEW | Chemical Society Reviews
Click chemistry with DNAw
Afaf H. El-Sagheerab and Tom Brown*a
Received 1st September 2009
First published as an Advance Article on the web 9th February 2010
DOI:
The advent of click chemistry has led to an influx of new ideas in the nucleic acids field.
The copper catalysed alkyne–azide cycloaddition (CuAAC) reaction is the method of choice for
DNA click chemistry due to its remarkable efficiency. It has been used to label oligonucleotides
with fluorescent dyes, sugars, peptides and other reporter groups, to cyclise DNA, to synthesise
DNA catenanes, to join oligonucleotides to PNA, and to produce analogues of DNA with
modified nucleobases and backbones. In this critical review we describe some of the pioneering
work that has been carried out in this area (78 references).
Introduction Azides and unactivated alkynes are almost entirely un-
reactive towards the functional groups normally encountered
Click chemistry was developed to provide a simple method to join in nature; they react only with each other.
anic molecules in high yields under mild conditions The triazole unit is extremely stable, and is not toxic.
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and in the presence of a diverse range of functional groups. The In this review we describe the use of click chemistry across
best example of this new class of extremely efficient chemical the nucleic acids field, focusing on synthetic strategies and
I
reactionsistheCu catalysed [3+2] azide–alkyne cycloaddition briefly d