2'-脱氧-5-[(1E)-3-[(三氟乙酰基)氨基]-1-丙烯基]尿苷 | 115794-55-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 2'-脱氧-5-[(1E)-3-[(三氟乙酰基)氨基]-1-丙烯基]尿苷
• 中文别名: -脱氧-5-[(1E)-3-[(三氟乙酰基)氨基]-1-丙烯基]尿苷；5-[3-(三氟乙酰氨基)-e-1-丙烯基]-2-脱氧尿苷；【5-修饰核苷】TFA-aa-dU
• 英文名称: 5-(3''-trifluoroacetamidoallyl)-2'-deoxyuridine
• 英文别名: 5-(3-trifluoracetylaminopropenyl)-2'-deoxyuridine；TFA-aa-dU；2,2,2-trifluoro-N-[(E)-3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-enyl]acetamide
• CAS: 115794-55-3
• 化学式: C₁₄H₁₆F₃N₃O₆
• 分子量: 379.293
• InChiKey: MBPYSSRDTGXWJD-HFVMFMDWSA-N

物化性质

• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  9

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  2'-脱氧-5-[(1E)-3-[(三氟乙酰基)氨基]-1-丙烯基]尿苷 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 9H-fluoren-9-ylmethyl N-[(2R)-1-[[(E)-3-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-enyl]amino]-3-(tert-butyldisulfanyl)-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  A cysteine-appended deoxyuridine for the postsynthetic DNA modification using native chemical ligation

  摘要：

  A new deoxyuridine derivative 6 bearing a cysteine group at the C5 position was synthesized and incorporated into oligodeoxynucleotide (ODN) by phosphoramidite chemistry. The postsynthetic DNA modification of the cysteine-containing ODN using native chemical ligation with thioesters of biotin and green fluorescent protein variant was successfully demonstrated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.018
• 作为产物：
  描述：

  N-烯丙基-2,2,2-三氟乙酰胺 、 5-(chloromercuri)-2'-deoxyuridine 在 potassium tetrachloropalladate(II) 、 sodium acetate 作用下， 反应 72.0h， 以49%的产率得到2'-脱氧-5-[(1E)-3-[(三氟乙酰基)氨基]-1-丙烯基]尿苷
  参考文献：
  名称：

  Toward an RNaseA Mimic:  A DNAzyme with Imidazoles and Cationic Amines

  摘要：

  Site-specific RNA cleavage has received considerable attention over the years. Directed synthesis to append imidazoles or amines or both to oligonucleotides to target specific RNA cleavage represents an exciting avenue of research. However, to date catalysis by such synthetic constructs, particularly in terms of turnover, has been difficult to observe. This is the first report of a truly catalytic M2+-independent DNAzyme synthetically modified with imidazoles and cationic amines that would seem to mimic RNaseA. This work now demonstrates how synthetic organic chemistry, when merged with combinatorial selection, can result in a new class of DNAzymes that meets the ongoing synthetic challenges for developing relatively small biomimetic catalysts.

  DOI：

  10.1021/ja0205075

文献信息

• Single-stranded labelled oligonucleotides, reactive monomers and methods
  申请人：Syngene, Inc.

  公开号：US04948882A1

  公开（公告）日：1990-08-14

  Substantially pure single-stranded oligonucleotides having a preselected sequence of not more than about 200 nucleotides, at least one of which is at a preselected position in the sequence and includes a base with a covalently attached linker arm containing or capable of binding at least one reporter group or solid support. A process for the chemical synthesis of the substantially pure single-stranded oligonucleotide and modified nucleosides useful in such synthesis are provided.

  本发明提供了具有预选序列的实质纯的单链寡核苷酸，其长度不超过约200个核苷酸，其中至少一个核苷酸位于序列中的预选位置，并包括具有共价连接的连接臂的碱基，该连接臂含有或能够结合至少一个报告基团或固体支持物。本发明还提供了化学合成实质纯单链寡核苷酸和用于该合成的修饰核苷酸的方法。
• System for delivering therapeutic agents into living cells and cells nuclei
  申请人：Segev David

  公开号：US20060160763A1

  公开（公告）日：2006-07-20

  A novel class of oligomeric compounds designed for forming conjugates with biologically active substances and delivering these substances to a desired bodily target are disclosed. Novel conjugates of these oligomeric compounds and biologically active moieties, pharmaceutical compositions containing such conjugates, and uses thereof as delivery systems for delivering the biologically active substances to a desired target are further disclosed. Processes of preparing the conjugates and the oligomeric compounds and novel intermediates designed for and used in these processes are also disclosed.

  本发明披露了一种新型寡聚化合物，旨在与生物活性物质形成共轭物，并将这些物质传递到所需的身体靶点。本发明还披露了这些寡聚化合物和生物活性基团的新型共轭物，包含这种共轭物的药物组合物以及将其用作传递生物活性物质到所需靶点的传递系统的用途。本发明还披露了制备共轭物和寡聚化合物的过程以及设计和用于这些过程的新型中间体。
• <i>Ketone</i>-DNA:  A Versatile Postsynthetic DNA Decoration Platform
  作者：Subhakar Dey、Terry L. Sheppard

  DOI：10.1021/ol016626r

  日期：2001.12.1

  [GRAPHICS]A general strategy for the functional diversification of DNA, oligonucleotides under physiological conditions was developed. We describe the synthesis of DNA molecules bearing ketone ports (ketone-DNA) and the efficient postsynthetic decoration of ketone-DNA with structurally diverse aminooxy compounds.
• Expanding the Potential of DNA for Binding and Catalysis: Highly Functionalized dUTP Derivatives That Are Substrates for Thermostable DNA Polymerases
  作者：Kandasamy Sakthivel、Carlos F. Barbas III

  DOI：10.1002/(sici)1521-3773(19981102)37:20<2872::aid-anie2872>3.0.co;2-5

  日期：1998.11.2

  The discovery of a simple structural motif allows for the enzymatic synthesis by polymerase chain reactions (PCR) of modified DNA (see reaction scheme) bearing side chains similar or even identical to those of several amino acids. Libraries of DNA functionalized with both cationic and anionic groups may now be readily prepared. R=I, HgCl; X=functional group.
• EP0135587A4
  申请人：——

  公开号：EP0135587A4

  公开（公告）日：1986-04-02