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

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

Pyrrole- and indole-linked C(8)-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 prom...

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Veröffentlicht in:Organic & biomolecular chemistry 2011-01, Vol.9 (5), p.1565-1571
Hauptverfasser: Schlitt, Katherine M, Millen, Andrea L, Wetmore, Stacey D, Manderville, Richard A
Format: Artikel
Sprache:eng
Schlagworte:
Base Pairing
Deoxyguanosine - chemistry
DNA - chemistry
Fluorescence
Fluorescent Dyes - chemistry
Hydrogen Bonding
Indoles - chemistry
Models, Molecular
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Zusammenfassung:Pyrrole- and indole-linked C(8)-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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00883d