5'-O-(4,4-dimethoxytrityl)-3'-O-[2-cyanoethxy-(N,N-diisopropylamino)-phosphino]-5-vinyl-2'-deoxyuridine | 287980-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4-dimethoxytrityl)-3'-O-[2-cyanoethxy-(N,N-diisopropylamino)-phosphino]-5-vinyl-2'-deoxyuridine
• 英文别名: 3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-ethenyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 287980-24-9
• 化学式: C₄₁H₄₉N₄O₈P
• 分子量: 756.836
• InChiKey: DTIGDKGQABDJTJ-VPJZQFIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  54.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  137.27
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1H-1,2,4-三唑 、 5'-O-(4,4-dimethoxytrityl)-3'-O-[2-cyanoethxy-(N,N-diisopropylamino)-phosphino]-5-vinyl-2'-deoxyuridine 在 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以95%的产率得到Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-oxo-4-[1,2,4]triazol-1-yl-5-vinyl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Template-directed reversible photocircularization of DNA via 5-vinyldeoxycytidine

  摘要：

  An efficient and reversible template-directed photoligation of oligodeoxynucleotides (ODNs) using 5-vinyldeoxycytidine (C-V) was described. When ODN containing C-V at the 5' end was photoirradiated with ODN containing thymine at the 3' end in the presence of a template ODN, an efficient photoligation was observed. Reversible photopadlocking of a circular DNA by the photocircularization using C-V was demonstrated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01025-x
• 作为产物：
  描述：

  5-乙烯基-2'-脱氧尿苷 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 5'-O-(4,4-dimethoxytrityl)-3'-O-[2-cyanoethxy-(N,N-diisopropylamino)-phosphino]-5-vinyl-2'-deoxyuridine
  参考文献：
  名称：

  WO2023/150867

  摘要：

  公开号：

文献信息

• Chemoselective Modification of Vinyl DNA by Triazolinediones
  作者：Anu Naik、Jawad Alzeer、Therese Triemer、Anna Bujalska、Nathan W. Luedtke

  DOI：10.1002/anie.201702554

  日期：2017.8.28

  A new method for the post‐synthetic modification of nucleic acids was developed that involves mixing a phenyl triazolinedione (PTAD) derivative with DNA containing a vinyl nucleobase. The resulting reactions proceeded through step‐wise mechanisms, giving either a formal [4+2] cycloaddition product, or, depending on the context of nucleobase, PTAD addition along with solvent trapping to give a secondary

  已开发出一种新的核酸合成后修饰方法，该方法涉及将苯基三唑啉二酮（PTAD）衍生物与含有乙烯基核碱基的DNA混合。最终的反应通过逐步机制进行，给出了正式的[4 + 2]环加成产物，或者取决于核碱基的情况，还添加了PTAD以及溶剂捕集，从而在水中形成仲醇。PTAD与5-乙烯基-2'-脱氧尿苷（VdU）的末端烯烃之间的无催化剂加成异常快，其二级速率常数为2×10 3  m -1  s -1。PTAD衍生物以构象选择性的方式与含VdU的寡核苷酸选择性反应，与双链体DNA相比，G-四链体的收率更高。这些结果证明了DNA无铜生物缀合的新策略，可用于探测细胞中的核酸构象。
• Detection of methylcytosine by DNA photoligation via hydrophobic interaction of the alkyl group
  作者：Masayuki Ogino、Yuuta Taya、Kenzo Fujimoto

  DOI：10.1039/b904941j

  日期：——

  We report the nonenzymatic detection of 5-methylcytosine by using template-directed photoligation through 5-vinyl-2′-deoxyuridine derivatives with high selectivity. In this paper, we propose a new detection method by using hydrophobic interaction. The photoligation yield of the 5-methylcytosine case was approximately 5.6-fold higher than that in the case of cytosine.

  我们报告了通过使用模板引导的光连接通过 5-乙烯基-2'-脱氧尿苷衍生物进行高选择性的 5-甲基胞嘧啶非酶检测。在本文中，我们提出了一种利用疏水相互作用的新检测方法。 5-甲基胞嘧啶情况的光连接产率比胞嘧啶情况高约5.6倍。
• A Kinetic and Fluorogenic Enhancement Strategy for Labeling of Nucleic Acids
  作者：Morten O. Loehr、Nathan W. Luedtke

  DOI：10.1002/anie.202112931

  日期：2022.5.23

  A novel acridine–tetrazine probe “PINK” was designed to overcome previous shortcomings of bioorthogonal labeling within tightly packed chromatin of living cells. High-affinity intercalation of the probe enhances its inverse electron-demand Diels–Alder reaction with vinyl-modified nucleic acids in both a kinetic and fluorogenic manner to allow for a “mix and measure” assay for DNA replication and RNA

  一种新型吖啶-四嗪探针“PINK”旨在克服以前在活细胞紧密堆积的染色质内进行生物正交标记的缺点。探针的高亲和力嵌入以动力学和荧光方式增强了其与乙烯基修饰的核酸的逆电子需求 Diels-Alder 反应，从而允许对活细胞中的 DNA 复制和 RNA 合成进行“混合和测量”测定。