Furan decorated nucleoside analogues as fluorescent probes: synthesis, photophysical evaluation, and site-specific incorporation
Furan decorated nucleoside analogues as fluorescent probes: synthesis, photophysical evaluation, and site-specific incorporation
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DOI：
10.1016/j.tet.2007.01.073
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发表时间：
2007-04-23
期刊：
影响因子：
2.1
通讯作者：
Tor, Yitzhak
中科院分区：
文献类型：
--
作者：
Greco, Nicholas J.;Tor, Yitzhak
本文报道了在2 '-脱氧尿苷5位上引入五元杂环（呋喃、噻吩、恶唑和噻唑）的核苷类似物的合成和物理性质的评价。含呋喃的衍生物由于其发射量子效率和对其微环境的敏感度而被鉴定为该家族中最有前途的响应性核苷。然后将呋喃部分连接到2 '-脱氧胞苷的5位以及腺苷和鸟苷的8位。这四个含呋喃的核苷类似物的光物理评价揭示了不同的吸收，发射和量子效率取决于类核苷（嘧啶或嘌呤）的明显差异。比较所有含呋喃核苷的生物物理性质，确定呋喃胸苷类似物，5-（呋喃-2-基）-2-脱氧尿苷，作为最佳的候选人，用作响应的荧光探针在核酸中。然后将5-（Fur-2-基）-2 '-脱氧尿苷转化为相应的亚磷酰胺，并以大于88%的偶联效率位点特异性地掺入DNA寡核苷酸中。这种呋喃修饰的寡核苷酸在与其互补DNA链杂交后形成稳定的双链体，并显示出有利的荧光特征。(c)2007爱思唯尔有限公司保留所有权利。
The synthesis and photophysical evaluation of modified nucleoside analogues in which a five-membered heterocycle (furan, thiophene, oxazole, and thiazole) is attached to the 5-position of 2'-deoxyuridine are reported. The furan-containing derivative is identified as the most promising responsive nucleoside of this family due to its emission quantum efficiency and degree of sensitivity to its microenvironment. The furan moiety was then attached to the 5-position of 2'-deoxycytidine as well as the 8-position of adenosine and guanosine. Photophysical evaluation of these four furan-containing nucleoside analogues reveals distinct differences in the absorption, emission, and quantum efficiency depending upon the class of nucleoside (pyrimidine or purine). Comparing the photophysical properties of all furan-containing nucleosides, identifies the furan thymidine analogue, 5-(fur-2-yl)-2-deoxyuridine, as the best candidate for use as a responsive fluorescent probe in nucleic acids. 5-(Fur-2-yl)-2'-deoxyuridine was then converted to the corresponding phosphoramidite and site specifically incorporated into DNA oligonucleotides with greater than 88% coupling efficiency. Such furan-modified oligonucleotides form stable duplexes upon hybridization to their complementary DNA strands and display favorable fluorescent features. (c) 2007 Elsevier Ltd. All rights reserved.