5-(3-Trifluoroacetamido-1-propynyl)-2',3'-dideoxy-uridine | 114748-60-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(3-Trifluoroacetamido-1-propynyl)-2',3'-dideoxy-uridine
• 英文别名: 5-(3-Trifluoroacetamido-1-propynyl)-2',3'-dideoxyuridine；5-(3-TRIFLUOROACETAMIDO-1-PROPYNYL)2',3'-DIDEOXYURIDINE；5-TFA-ap-ddU；2,2,2-trifluoro-N-[3-[1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-ynyl]acetamide
• CAS: 114748-60-6
• 化学式: C₁₄H₁₄F₃N₃O₅
• 分子量: 361.277
• InChiKey: YZMXEAFWOQOJCL-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(3-Trifluoroacetamido-1-propynyl)-2',3'-dideoxy-uridine 生成 5-(3-AMINO-1-PROPYNYL)-2',3'-DIDEOXYURIDINE 5'-TRIPHOSPHATE
  参考文献：
  名称：

  Method of gene mapping

  摘要：

  描述的方法是通过将每个要映射的DNA片段切割，产生DNA片段，然后用特定于每个片段末端核苷酸的报告物质对其进行末端标记来表征每个DNA片段。标记的片段再次被切割，产生根据大小分离的短片段。这些短片段被分析以确定报告的标识和大小，这表明了每个片段的特性。通过对初级切割片段的切割末端进行衍生化，标记可以延迟到第二次切割之前。在对衍生化片段进行标记之前，所有未衍生化的片段都被去除，衍生化的片段被固定。

  公开号：

  US05102785A1
• 作为产物：
  描述：

  2',3'-二脱氧尿苷 在 copper(l) iodide 、 四(三苯基膦)钯 一氯化碘 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 5-(3-Trifluoroacetamido-1-propynyl)-2',3'-dideoxy-uridine
  参考文献：
  名称：

  Confalone, Pat. N., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 1, p. 31 - 46

  摘要：

  DOI：

文献信息

• A ligand-free solid-supported system for Sonogashira couplings: applications in nucleoside chemistry
  作者：Neil K. Garg、Carolyn C. Woodroofe、Christopher J. Lacenere、Stephen R. Quake、Brian M. Stoltz

  DOI：10.1039/b505737j

  日期：——

  A mild heterogeneous, ligand-free protocol for Sonogashira and Heck couplings has been developed and used to access several biologically important deoxynucleoside derivatives in a facile manner.

  开发了一种温和的、多相的、无配体的Sonogashira和Heck偶联反应协议，并已用于便捷地合成多种生物重要的脱氧核苷衍生物。
• Solvent, not palladium oxidation state, is the primary determinant for successful coupling of terminal alkynes with iodo-nucleosides
  作者：Morris J. Robins、Ravi S. Vinayak、Steven G. Wood

  DOI：10.1016/s0040-4039(00)97456-2

  日期：——

  Coupling of iodo-nucleosides with terminal alkynes such as 3-(acylamino)propynes, whose initial products readily undergo secondary cyclization reactions, can be effected smoothly by the standard catalysis with (Ph3P)2PdCl2/CuI/Et3N in dimethylformamide.

  碘代核苷与末端炔烃（例如3-（酰基氨基）丙炔）的偶联，其初始产物容易发生二级环化反应，可以通过（Ph 3 P）2 PdCl 2 / CuI / Et 3 N in二甲基甲酰胺。
• Alkynylamino-nucleotides
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05151507A1

  公开（公告）日：1992-09-29

  Alkynylamino-nucleotides and labeled alkynylaminonucleotides useful, for example, as chain terminating substrates for DNA sequencing are provided along with several key intermediates and processes for their preparation. For some applications, longer, hydrophilic linkers are provided.

  提供了Alkynylamino-核苷酸和标记的Alkynylamino-核苷酸，例如，作为DNA测序的链终止底物，并提供了几个关键中间体和它们的制备过程。对于某些应用，还提供了更长的亲水性连接剂。
• Method, system and reagents for DNA sequencing
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05608063A1

  公开（公告）日：1997-03-04

  A DNA sequencing system and method are described to detect the presence of radiant energy emitted from different excited reporter dye-labeled species (DNA fragments) following separation in time and/or space, and the identity of the species which emit radiant energy closely spaced in wavelength. Functions of the emitted energy are obtained which vary over the wavelengths of the closely spaced spectra in different senses and the functions ratioed, whereby the ratio is indicative of the identity of the DNA fragments. The emitting portion of the reporter-labeled DNA fragment is preferably one of a family of fluorescent dyes based on 9-carboxyethyl-6-hydroxy-3 -oxo-3H-xanthene. These xanthene dyes are covalently attached to the DNA fragments through the carboxylic acid functionality, preferably via an amide linkage. The dyes may be protected by including an alkoxy group at the 9-position. A spacer may be inserted between the dye and the amine. The fluorescent dye preferably is attached to the DNA chain terminators and provides many advantages. Thus only DNA sequencing fragments resulting from bona fide termination events will carry a reporter. The DNA sequencing may also be labeled using the xanthene dyes which have general utility as fluorescent labels. Also acyclonucleoside triphosphates are described as being useful as chain terminators in DNA sequencing using a modification of the Sanger method.

  本文介绍了一种DNA测序系统和方法，用于检测不同激发报告染料标记物（DNA片段）分离后发射的辐射能量的存在，并且在波长紧密相邻的物种中发射辐射能量的身份。获得的发射能量函数在不同的波长范围内以不同的方式变化，并且对函数进行比率，因此比率表明DNA片段的身份。报告标记的DNA片段的发射部分最好是基于9-羧基乙基-6-羟基-3-氧代-3H-黄色素的荧光染料家族之一。这些黄色素染料通过羧酸功能性与DNA片段共价连接，最好通过酰胺键连接。染料可以通过在9位点包括烷氧基来保护。染料和胺之间可以插入间隔物。荧光染料最好连接到DNA链终止剂上，并提供许多优点。因此，只有由真正的终止事件产生的DNA测序片段才会携带报告。DNA测序也可以使用具有一般荧光标记实用性的黄色素染料进行标记。此外，本文还描述了使用Sanger方法的修改来使用无环核苷酸三磷酸盐作为链终止剂的有用性。
• Fluorescent dye intermediates
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05625081A1

  公开（公告）日：1997-04-29

  Intermediates for fluorescent dyes based on 9-carboxyethyl-6-hydroxy-3-oxo-3H-xanthene which are useful as reporters for reporter-labeled DNA fragments are described. The intermediates are protected fluorescent dyes bearing acyloxy groups at the 3 and 9 positions and an alkoxy group at the 9 position. Deprotection of the protected fluorescent dye by treatment with aqueous ammonia regenerates free dye.

  本文描述了基于9-羧乙基-6-羟基-3-氧代-3H-黄色素的荧光染料中间体，这些荧光染料中间体可作为标记DNA片段的报告物。该中间体是带有酰氧基团的保护荧光染料，其位于3和9位置，并且在9位置带有烷氧基团。通过用水溶氨处理保护荧光染料来去保护，可以再生自由染料。