To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (AT) and its photophysical characterization inside DNA. AT shows promising properties compared to the widely used adenine analogue 2-aminopurine. Quantum yields reach >20% and >5% in single- and double-stranded DNA, respectively, and show dependence on neighbouring bases. Moreover, AT shows only a minor destabilization of DNA duplexes, comparable to 2-aminopurine, and circular dichroism investigations suggest that AT only causes minimal structural perturbations to normal B-DNA. Furthermore, we find that AT shows favourable base-pairing properties with thymine and more surprisingly also with normal adenine. In conclusion, AT shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.
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机译:为了增加具有改进特性的荧光碱基类似物的多样性,我们在这里展示了一种基于点击化学的直接合成新的荧光腺嘌呤-类似物三唑腺嘌呤(A T sup>)及其在DNA内部的光物理特征。与广泛使用的腺嘌呤类似物2-氨基嘌呤相比,A T sup>具有良好的性能。单链和双链DNA的量子产率分别达到> 20%和> 5%,并显示出对相邻碱基的依赖性。此外,A T sup>仅显示了DNA双链体的轻微失稳,与2-氨基嘌呤相当,并且圆二色性研究表明,A T sup>仅对正常的B-引起最小的结构扰动。脱氧核糖核酸。此外,我们发现A T sup>与胸腺嘧啶显示出有利的碱基配对特性,更令人惊讶的是,与正常腺嘌呤也显示出这种碱基配对特性。总之,A T sup>具有强大的潜力,可以作为一种新型的荧光腺嘌呤类似物来监测其DNA微环境中的变化。
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