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Issue 5, 2011
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An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson–Crick versus Hoogsteen base pairing

Katherine M. Schlitt,a  Andrea L. Millen,b  Stacey D. Wetmore*b  and  Richard A. Manderville*a 
Author affiliations

* Corresponding authors

a Departments of Chemistry and Toxicology, University of Guelph, Guelph, Ontario, Canada
E-mail: rmanderv@uoguelph.ca
Fax: 1-519-766-1499
Tel: 1-519-824-4120 53963

b Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, Alberta, Canada
E-mail: stacey.wetmore@uleth.ca
Fax: 1-403-329-2057
Tel: 1-403-329-2323

Abstract

Pyrrole- and indole-linked C8-deoxyguanosine nucleosides act as fluorescent reporters of H-bonding specificity. Their fluorescence is quenched upon Watson–Crick H-bonding to dC, while Hoogsteen H-bonding to G enhances emission intensity. The indole-linked probe is ∼ 10-fold brighter and shows promise as a fluorescent reporter of Hoogsteen base pairing.

Graphical abstract: An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson–Crick versus Hoogsteen base pairing

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Publication details

The article was received on 14 Oct 2010, accepted on 22 Nov 2010 and first published on 23 Nov 2010


Article type: Paper
DOI: 10.1039/C0OB00883D
Citation: Org. Biomol. Chem., 2011,9, 1565-1571
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    An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson–Crick versus Hoogsteen base pairing

    K. M. Schlitt, A. L. Millen, S. D. Wetmore and R. A. Manderville, Org. Biomol. Chem., 2011, 9, 1565
    DOI: 10.1039/C0OB00883D

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