Fast and efficient DNA crosslinking and multiple orthogonal labelling by copper-free click chemistry

Montserrat Shelbourne; Tom Brown; Afaf H. El-Sagheer; Tom Brown

doi:10.1039/C2CC35084J

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Chemical Communications

Issue 91, 2012

Urgent high quality communications from across the chemical sciences.

Impact Factor 6.378 100 Issues per Year Indexed in MEDLINE

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Fast and efficient DNA crosslinking and multiple orthogonal labelling by copper-free click chemistry

Montserrat Shelbourne,^a Tom Brown,^b Afaf H. El-Sagheer*^a^c and Tom Brown*^a

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School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
E-mail: tb2@soton.ac.uk, A.H.El-Sagheer@soton.ac.uk;
Fax: +44 (0)2380 592991 ;
Tel: +44 (0)2380 592974

ATDBio Ltd, Highfield, Southampton SO17 1BJ, UK

Chemistry Branch, Dept. of Science and Mathematics, Suez Canal University, Suez 43721, Egypt

Chem. Commun., 2012,48, 11184-11186

DOI: 10.1039/C2CC35084J
Received 16 Jul 2012, Accepted 01 Aug 2012
First published online 03 Aug 2012

This article is part of themed collection: Nucleic acids: new life, new materials

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Two new dibenzocyclooctyne–thymidine monomers were incorporated into oligonucleotides and crosslinked to azide-labelled complementary strands across the DNA grooves. Equivalent reactions were successful using a (bicyclo[6.1.0]nonyne) alkyne. Oligonucleotides containing internal cyclooctyne and amino groups were simultaneously reacted with azides and NHS esters of different fluorescent dyes to produce functional genetic probes.