Preparation of 1-ethynylpyrene-modified DNA via Sonogashira-type solid-phase couplings and characterization of the fluorescence properties for electron-transfer studies
Preparation of 1-ethynylpyrene-modified DNA via Sonogashira-type solid-phase couplings and characterization of the fluorescence properties for electron-transfer studies
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DOI：
10.1002/ejoc.200300125
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发表时间：
2003-07-01
影响因子：
2.8
通讯作者：
Wagenknecht, HA
中科院分区：
文献类型：
--
作者：
Rist, M;Amann, N;Wagenknecht, HA
一系列的1-乙炔基芘修饰的寡核苷酸（Py-drop-dU）已通过一个特殊的半自动化的策略，使用Sonogashira型交叉偶联条件在固相中制备。Py-drop-dU修饰的单链及其相应的双链双链体的吸收和荧光性质已被表征。所提出的光谱表明，Py-drop-dU发射淬灭的DNA双链体轴承胸腺嘧啶或胞嘧啶相邻的Py-drop-dU组。这表明Py-drop-dU部分能够将电子注入到基极叠层中，同时充当光谱标记以能够观察这些过程。因此，Py-drop-dU修饰的寡核苷酸是很有前途的供体系统，以研究电子注入和电子传输的DNA光谱。I（（C）Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2003）。
A range of 1-ethynylpyrene-modified oligonucleotides (Py-drop-dU) has been prepared by a special semi-automated strategy using Sonogashira-type cross-coupling conditions in the solid phase. The absorption and fluorescence properties of the Py-drop-dU-modified single strands and their corresponding double-stranded duplexes have been characterized. The presented spectra show that the Py-drop-dU emission is quenched in DNA duplexes bearing a thymine or cytosine adjacent to the Py-drop-dU group. This shows that the Py-drop-dU moiety is able to inject an electron into the base stack while simultaneously acting as a spectroscopic label to enable the observation of these processes. Hence, Py-drop-dU-modified oligonucleotides are promising donor systems in order to study electron injection and electron transport in DNA spectroscopically. I ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).