(Z)-2,6-difluoro-4-((2-methyl-5-oxooxazol-4(5H)-ylidene)methyl)phenyl acetate | 1332478-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: (Z)-2,6-difluoro-4-((2-methyl-5-oxooxazol-4(5H)-ylidene)methyl)phenyl acetate
• 英文别名: [2,6-difluoro-4-[(Z)-(2-methyl-5-oxo-1,3-oxazol-4-ylidene)methyl]phenyl] acetate
• CAS: 1332478-75-7
• 化学式: C₁₃H₉F₂NO₄
• 分子量: 281.216
• InChiKey: KQBFSCSRJXXZPY-WZUFQYTHSA-N

物化性质

• 沸点：
  358.8±52.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-2,6-difluoro-4-((2-methyl-5-oxooxazol-4(5H)-ylidene)methyl)phenyl acetate 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以50%的产率得到(Z)-4-(3,5-difluoro-4-hydroxybenzylidene)-1-hydroxy-2-methyl-1Himidazol-5(4H)-one
  参考文献：
  名称：

  Plug-and-Play Fluorophores Extend the Spectral Properties of Spinach

  摘要：

  Spinach and Spinach2 are RNA aptamers that can be used for the genetic encoding of fluorescent RNA. Spinach2 binds and activates the fluorescence of (Z)-4-(3,5-difluoro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5 (4H)-one (DFHBI), allowing the dynamic localizations of Spinach2-tagged RNAs to be imaged in live cells. The spectral properties of Spinach2 are limited by DFHBI, which produces fluorescence that is bluish-green and is not optimized for filters commonly used in fluorescence microscopes. Here we characterize the structural features that are required for fluorophore binding to Spinach2 and describe novel fluorophores that bind and are switched to a fluorescent state by Spinach2. These diverse Spinach2 fluorophore complexes exhibit fluorescence that is more compatible with existing microscopy filter sets and allows Spinach2-tagged constructs to be imaged with either GFP or YFP filter cubes. Thus, these "plug-and-play" fluorophores allow the spectral properties of Spinach2 to be altered on the basis of the specific spectral needs of the experiment.

  DOI：

  10.1021/ja410819x
• 作为产物：
  描述：

  乙酸酐 、 3,5-二氟-4-羟基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 作用下， 反应 5.0h， 以77%的产率得到(Z)-2,6-difluoro-4-((2-methyl-5-oxooxazol-4(5H)-ylidene)methyl)phenyl acetate
  参考文献：
  名称：

  荧光团促进的RNA折叠和光稳定性使活哺乳动物细胞中单个西兰花标记的mRNA成像成为可能。

  摘要：

  菠菜和西兰花是发荧光的RNA适体，它们结合DFHBI（一种绿色荧光蛋白中的发色团的模拟物）并激活其荧光。菠菜/西兰花-DFHBI复合物在体外显示出高荧光，但在哺乳动物细胞中显示出较低的荧光。在这里，使用计算筛选来鉴定BI，这是一种DFHBI衍生物，与以前的配体相比，它以较高的亲和力结合西兰花，并导致细胞中的荧光明显更高。BI阻止了花椰菜在37°C时的热解折叠，从而导致花椰菜折叠得更多，从而使细胞中的花椰菜-BI荧光复合物含量更高。由于光致异构化受损和光致异构化的顺式-BI快速脱键，西兰花-BI复合物更耐光。这些特性使包含24个西兰花适体的单个mRNA能够在用BI处理的活哺乳动物细胞中成像。因此，小分子配体可以促进RNA在细胞中的折叠，从而可以利用荧光适体对单个mRNA进行成像。

  DOI：

  10.1002/anie.201914576

文献信息

• Bifacial Peptide Nucleic Acid as an Allosteric Switch for Aptamer and Ribozyme Function
  作者：Xin Xia、Xijun Piao、Dennis Bong

  DOI：10.1021/ja5032584

  日期：2014.5.21

  We demonstrate herein that bifacial peptide nucleic acid (bPNA) hybrid triplexes functionally substitute for duplex DNA or RNA. Structure-function loss in three non-coding nucleic acids was inflicted by replacement of a duplex stem with unstructured oligo-T/U strands, which are bPNA binding sites. Functional rescue was observed on refolding of the oligo-T/U strands into bPNA triplex hybrid stems. Bifacial

  我们在此证明双面肽核酸 (bPNA) 杂合三链体在功能上替代了双链体 DNA 或 RNA。三种非编码核酸的结构-功能丧失是通过用非结构化的寡-T/U 链（bPNA 结合位点）替换双链体茎造成的。在将寡-T/U 链重折叠为 bPNA 三重杂交茎时观察到功能性拯救。因此，双面 PNA 结合用于变构地开启 DNA 和 RNA 适体中的蛋白质和小分子结合，以及核酶中的催化键断裂。支持最小 I 型锤头状核酶催化位点的双链茎被 oligo-U 环取代，严重削弱或消除了天然 RNA 剪接功能。将 U 环重折叠为 bPNA 三重茎完全恢复了混合系统中的剪接功能。这些研究表明，bPNA 作为非编码核酸中广泛功能的变构触发器可能具有普遍效用。
• Dye‐Conjugated Spinach RNA by Genetic Alphabet Expansion
  作者：Kyung Hyun Lee、Michiko Kimoto、Gota Kawai、Itaru Okamoto、Andrea Fin、Ichiro Hirao

  DOI：10.1002/chem.202104396

  日期：2022.3.16

  Light emission by dye-conjugated Spinach RNA transcripts can be generated by genetic alphabet expansion. Dye-conjugated unnatural base substrates are site-specifically incorporated into Spinach RNA opposite to its unnatural base pairing partner in DNA templates by T7 transcription. The dye-conjugated Spinach RNAs or shorter versions robustly emit fluorescence.

  染料共轭菠菜 RNA 转录物的光发射可以通过遗传字母扩展产生。通过 T7 转录，染料结合的非天然碱基底物与 DNA 模板中的非天然碱基配对配对物以位点特异性结合到菠菜 RNA 中。染料结合的菠菜 RNA 或更短的版本会发出强烈的荧光。
• Understanding the Photophysics of the Spinach–DFHBI RNA Aptamer–Fluorogen Complex To Improve Live-Cell RNA Imaging
  作者：Kyu Young Han、Benjamin J. Leslie、Jingyi Fei、Jichuan Zhang、Taekjip Ha

  DOI：10.1021/ja411060p

  日期：2013.12.18

  The use of aptamer-fluorogen complexes is an emerging strategy for RNA imaging. Despite its promise for cellular imaging and sensing, the low fluorescence intensity of the Spinach-DFHBI RNA aptamer fluorogen complex hampers its utility in quantitative live-cell and high-resolution imaging applications. Here we report that illumination of the Spinach fluorogen complex induces photoconversion and subsequently fluorogen dissociation, leading to fast fluorescence decay and fluorogen-concentration-dependent recovery. The fluorescence lifetime of Spinach DFHBI is 4.0 +/- 0.1 ns irrespective of the Spinach DFHBI RNA imaging tag in living cells.
• COMPOSITIONS AND METHODS FOR DETECTING AN ABASIC SITE
  申请人：ILLUMINA, INC.

  公开号：US20220090179A1

  公开（公告）日：2022-03-24

  A method for detecting an abasic site is provided. The method may include flowing a solution over a substrate having a plurality of oligonucleotides coupled thereto. At least one of the oligonucleotides includes an abasic site. The solution may include a fluorophore coupled to a reactive group. The method may include reacting the reactive group with the abasic site to couple the fluorophore to the abasic site; and detecting the abasic site using fluorescence from the fluorophore.
• [EN] COMPOSITIONS AND METHODS FOR DETECTING AN ABASIC SITE OF A NUCLEIC ACID<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE DÉTECTION D'UN SITE ABASIQUE D'UN ACIDE NUCLÉIQUE
  申请人：ILLUMINA INC

  公开号：WO2022056169A1

  公开（公告）日：2022-03-17

  A method for detecting an abasic site is provided. The method may include flowing a solution over a substrate having a plurality of oligonucleotides coupled thereto. At least one of the oligonucleotides includes an abasic site. The solution may include a fluorophore coupled to a reactive group. The method may include reacting the reactive group with the abasic site to couple the fluorophore to the abasic site; and detecting the abasic site using fluorescence from the fluorophore.