8-phenylethynyl-2'-deoxyguanosine | 209785-83-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-phenylethynyl-2'-deoxyguanosine
• 英文别名: 8-(phenylethynyl)-2′-deoxyguanosine；8-(2-phenylethyn-1-yl)-2'-deoxyguanosine；2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-(2-phenylethynyl)-1H-purin-6-one
• CAS: 209785-83-1
• 化学式: C₁₈H₁₇N₅O₄
• 分子量: 367.364
• InChiKey: LHLVGXXJQIMLLZ-OUCADQQQSA-N

物化性质

• 密度：
  1.60±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-phenylethynyl-2'-deoxyguanosine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以40%的产率得到(Z)-8-styryl-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis and reversible photoisomerization of photoswitchable nucleoside, 8-styryl-2′-deoxyguanosine

  摘要：

  A novel guanosine derivative with a photoswitching property, 8-styryl-2'-deoxyguanosine was synthesized, and showed very rapid and efficient reversible E-Z photoisomerization upon illumination at specific wavelength. In addition, E-Z photoisomerization can be iteratively performed by alternate illumination with monochroic 254 nm and 370 nm light without any side reactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.124
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.0h， 生成 8-phenylethynyl-2'-deoxyguanosine
  参考文献：
  名称：

  使用苯基乙炔鸟嘌呤Nucleobase跟踪DNA发夹中的空穴传输。

  摘要：

  已经研究了具有electron电子受体和供体以及修饰的鸟嘌呤（G）核碱基，特别是8-（4'-苯基乙炔基）脱氧鸟苷或EG的DNA发夹的空穴传输动力学。EG和G几乎难以区分的氧化电位和EG +•的独特光谱特征使其非常适合直接观察在二苯乙烯电子供体和受体之间的电荷传输过程中的瞬时空穴占据。与阳离子自由基G +•相比，EG +•在460 nm附近具有强吸收，并具有独特的拉曼活性乙炔基伸展度。两种光谱特征都容易与二苯乙烯供体/受体自由基离子发色团的光谱特征区分开。使用EG，我们观察到它作为浅孔陷阱或当存在较深陷阱状态时作为中间空穴传输位点的作用。结合使用超快吸收和受激拉曼光谱，在具有EG vs G碱的系统中，空穴传输动力学相似，对电荷传输速率和产率的扰动很小。这些结果表明，EG可以在整个序列中的指定位置进行部署，以报告空穴的占用情况，从而可以通过碱基位点特异性对空穴传输动力学进行详细监控。

  DOI：

  10.1021/jacs.7b06998

文献信息

• Efficient Sonogashira Coupling of Unprotected Halonucleosides in Aqueous Solvents Using Water-Soluble Palladium Catalysts
  作者：Joon Hyung Cho、Caitlin D. Prickett、Kevin H. Shaughnessy

  DOI：10.1002/ejoc.201000313

  日期：2010.7

  prompted the continuing development of efficient synthetic methods for their preparation. We report an efficient andenvironmentally benign Sonogashira coupling reaction for alkynylation of unprotected halonucleosides in an aqueous solvent. The combination of Pd(OAc)2, CuI, and TXPTS [trisodium tri(2,4-dimethyl-5-sulfonatophenyl)phosphane] provided an effective catalyst for the alkynylation of 8-bromopurines

  C-炔基化核苷的各种应用促进了其制备的有效合成方法的持续发展。我们报告了一种有效且对环境无害的 Sonogashira 偶联反应，用于在水性溶剂中对未受保护的卤代核苷进行炔基化。Pd(OAc)2、CuI 和 TXPTS [三(2,4-二甲基-5-磺基苯基)膦三钠] 的组合为 H2O/CH3CN 中 8-溴嘌呤和 5-碘尿苷的炔基化提供了有效的催化剂 (1 :1) 产率范围为 42 至 98 %。
• Design of environmentally sensitive fluorescent 2′-deoxyguanosine containing arylethynyl moieties: Distinction of thymine base by base-discriminating fluorescent (BDF) probe
  作者：Yuta Shinohara、Katsuhiko Matsumoto、Kenji Kugenuma、Takashi Morii、Yoshio Saito、Isao Saito

  DOI：10.1016/j.bmcl.2010.03.055

  日期：2010.5

  We have synthesized various substituted 8-arylethynylated 2'-deoxyguanosine derivatives. Among them, acetyl substituted deoxyguanosine analogue 4c showed a remarkable solvent dependent fluorescence property, that is, an intense fluorescence in non-polar solvents but extremely weak fluorescence in polar solvents like methanol. By using solvatofluorochromic deoxyguanosine analogue 4c, we have developed highly thymine (T) selective fluorescent DNA probes that can sense T opposite 4c in a target DNA regardless of the flanking sequences. We were able to demonstrate that 4c can be used as a T specific base-discriminating fluorescent (BDF) nucleoside in homogeneous fluorescence assay. (C) 2010 Elsevier Ltd. All rights reserved.
• N²- and C⁸-Substituted Oligodeoxynucleotides with Enhanced Thrombin Inhibitory Activity in Vitro and in Vivo
  作者：Gong-Xin He、Steven H. Krawczyk、S. Swaminathan、Regan G. Shea、Joseph P. Dougherty、Terry Terhorst、Veronica S. Law、Linda C. Griffin、Steven Coutré、Norbert Bischofberger

  DOI：10.1021/jm970434d

  日期：1998.6.1

  2'-Deoxyguanosine (G) analogues carrying various hydrophobic substituents in the N-2 and C-8 positions were synthesized and introduced through solid-phase synthesis into 15-mer oligodeoxynucleotide, GGTTGGTGTGGTTGG, which forms a chairlike structure consisting of two G-tetrads and is a potent thrombin inhibitor. The effects of the substitutions at N-2 and C-8 of the G-tetrad-forming G residues on the thrombin inhibitory activity are relatively small, suggesting that these substitutions cause relatively small, perturbations on the chairlike structure formed by the oligodeoxynucleotide. Introduction of a benzyl group into N-2 of G(6) and G(11) and naphthylmethyl groups into N-2 of G(6) increased the thrombin inhibitory activity, whereas other substituents in these positions had almost no effect or decreased the activity. Particularly, the oligodeoxynucleotide carrying a 1-naphthylmethyl group in the N-2 position of G(6) showed an increase in activity by about 60% both in vitro and in vivo. Substitutions on the N-2 position of other G residues had little effect or decreased the activity. Introduction of a relatively small group, such as methyl and propynyl, into the C-8 positions of G(1), G(5), G(10), and G(14) increased the activity, presumably due to the stabilization of a chairlike structure, whereas introduction of a large substituent group, phenylethynyl, decreased the activity, probably due to the steric hindrance.
• Fluorometric detection of adenine in target DNA by exciplex formation with fluorescent 8-arylethynylated deoxyguanosine
  作者：Yoshio Saito、Kenji Kugenuma、Makiko Tanaka、Azusa Suzuki、Isao Saito

  DOI：10.1016/j.bmcl.2012.04.011

  日期：2012.6

  We demonstrated an intriguing method to discriminate adenine by incident appearance of an intense new emission via exciplex formation in hybridization of target DNA with newly designed fluorescent 8-arylethynylated deoxyguanosine derivatives. We described the synthesis of such highly electron donating fluorescent guanosine derivatives and their incorporation into DNA oligomers which may be used for the structural study and the fluorometric analysis of nucleic acids. (C) 2012 Elsevier Ltd. All rights reserved.
• Tracking Hole Transport in DNA Hairpins Using a Phenylethynylguanine Nucleobase
  作者：Kristen E. Brown、Arunoday P. N. Singh、Yi-Lin Wu、Ashutosh Kumar Mishra、Jiawang Zhou、Frederick D. Lewis、Ryan M. Young、Michael R. Wasielewski

  DOI：10.1021/jacs.7b06998

  日期：2017.8.30

  The hole transport dynamics of DNA hairpins possessing a stilbene electron acceptor and donor along with a modified guanine (G) nucleobase, specifically 8-(4′-phenylethynyl)deoxyguanosine, or EG, have been investigated. The nearly indistinguishable oxidation potentials of EG and G and unique spectroscopic characteristics of EG+• make it well-suited for directly observing transient hole occupation during

  已经研究了具有electron电子受体和供体以及修饰的鸟嘌呤（G）核碱基，特别是8-（4'-苯基乙炔基）脱氧鸟苷或EG的DNA发夹的空穴传输动力学。EG和G几乎难以区分的氧化电位和EG +•的独特光谱特征使其非常适合直接观察在二苯乙烯电子供体和受体之间的电荷传输过程中的瞬时空穴占据。与阳离子自由基G +•相比，EG +•在460 nm附近具有强吸收，并具有独特的拉曼活性乙炔基伸展度。两种光谱特征都容易与二苯乙烯供体/受体自由基离子发色团的光谱特征区分开。使用EG，我们观察到它作为浅孔陷阱或当存在较深陷阱状态时作为中间空穴传输位点的作用。结合使用超快吸收和受激拉曼光谱，在具有EG vs G碱的系统中，空穴传输动力学相似，对电荷传输速率和产率的扰动很小。这些结果表明，EG可以在整个序列中的指定位置进行部署，以报告空穴的占用情况，从而可以通过碱基位点特异性对空穴传输动力学进行详细监控。