Issue 11, 2009
From the journal:

Organic & Biomolecular Chemistry

Pyrene acetylide nucleotides in GNA: probing duplex formation and sensing of copper(II) ions†

Hui Zhou,a   Xiaoyan Ma,bc   Jianpian Wangb  and  Lilu Zhang*a  

* Corresponding authors

a Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, Marburg, Germany
E-mail: zhangl@staff.uni-marburg.de
Fax: +49-6421-2822189
Tel: +49-6421-2825600

b Beijing National Laboratory for Molecular Science, State Key Laboratory of Molecular Reaction Dynamics, Institute of Chemistry, Chinese Academy of Science, No.2, First North Street, Zhongguancun, Beijing, China

c Graduate School of Chinese Academy of Sciences, Beijing, China

Abstract

The synthesis and evaluation of GNA duplexes containing fluorescent pyrene and pyrene acetylide nucleotides is reported. Interestingly, only the pyrene acetylides, but not the related plain pyrene nucleotides, form strong excimers upon stacking in glycol nucleic acid (GNA) duplexes. The ability of the large pyrene acetylide nucleotide to be accommodated in GNA duplexes opposite an abasic site was investigated by molecular modeling. The interstrand pyrene acetylide excimer formation was used to monitor GNA duplex formation and was applied to the design of a copper(II)-selective “turn-on” fluorescence sensor.

Graphical abstract: Pyrene acetylide nucleotides in GNA: probing duplex formation and sensing of copper(II) ions

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Article information

DOI
https://doi.org/10.1039/B900167K
Article type
Paper
Submitted
06 Jan 2009
Accepted
05 Mar 2009
First published
14 Apr 2009

Org. Biomol. Chem., 2009,7, 2297-2302

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Pyrene acetylide nucleotides in GNA: probing duplex formation and sensing of copper(II) ions

H. Zhou, X. Ma, J. Wang and L. Zhang, Org. Biomol. Chem., 2009, 7, 2297 DOI: 10.1039/B900167K

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