2-cyanoethyl Ν,Ν,Ν',Ν'-tetraisopropylphosphorodiamidite

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyanoethyl Ν,Ν,Ν',Ν'-tetraisopropylphosphorodiamidite
• 英文别名: 2-cyanoethyl-N,N,N',N'-tetraisopropylaminophosphine；(2-cyanoethyl)di(N,N-diisopropylamino)phosphine；2-cyanoethyl-N,N,N,N-tetraisopropyl-phosphane；(i-Pr2N)2POCH2CH2CN；bis(N,N-diisopropylamino)-cyanoethyl phosphine；3-Bis[di(propan-2-yl)amino]phosphanylpropanenitrile
• 化学式: C₁₅H₃₂N₃P
• 分子量: 285.413
• InChiKey: FZQDHMFHGFAKMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3'-O-(二甲氧基三苯甲基)丙基][3-羟基丙基]二硫化物 、 2-cyanoethyl Ν,Ν,Ν',Ν'-tetraisopropylphosphorodiamidite 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-O-(4,4'-dimethoxytritylpropyldisulfide)-1'-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite
  参考文献：
  名称：

  The ODN probes conjugating the Cu(II) complex enhance the luminol chemiluminescence by assembling on the DNA template

  摘要：

  Potent peroxidase-like activity of the beta-ketoenamine (1)-dicopper (II) complex (2) for the chemiluminescence (CL) of luminol either in the presence or absence of H2O2 has been previously demonstrated by our group. In this study, the beta-ketoenamine (1) as the ligand unit for copper(II) was incorporated into the oligonucleotide (ODN) probes. It has been shown that the catalytic activity of the ODN probes conjugating the ligand-Cu(II) complex is activated by hybridization with the target DNA with the complementary sequence. Thus, this study has successfully demonstrated the basic concept for the sensitive detection of nucleic acids by CL based on the template-inductive activation of the catalytic unit for CL. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.007
• 作为产物：
  描述：

  二异丙胺 、 3-羟基丙腈 在 三氯化磷 作用下， 以 乙腈 、 正庚烷 为溶剂， 反应 5.0h， 生成 2-cyanoethyl Ν,Ν,Ν',Ν'-tetraisopropylphosphorodiamidite
  参考文献：
  名称：

  [EN] PREPARATION OF PURIFIED PHOSPHORODIAMIDITE
  [FR] PRÉPARATION DE PHOSPHORODIAMIDITE PURIFIÉ

  摘要：

  该瞬时发明涉及一种磷酰二胺酯生产方法，包括：(E1) 准备一种纯化的二烷基胺在极性溶剂中的溶液，步骤如下：- 将溶解在极性溶剂中的二烷基胺与足以与二烷基胺中含有的醇杂质反应但足够低以使大部分二烷基胺未反应的磷酰三卤化物接触，从而获得含有二烷基胺和磷酰三卤化物与杂质反应产物的混合物；- 通过其挥发度的差异，通常通过蒸馏，从步骤(E1.1.)获得的混合物中提取未反应的二烷基胺和极性溶剂，从而获得含有二烷基胺在极性溶剂中的纯化溶液；(E2) 在步骤(E1)中获得的二烷基胺在极性溶剂中的纯化溶液与磷酰三卤化物反应，从而形成中间化合物；(E3) 在步骤(E2)中获得的中间化合物在非极性共溶剂存在下与羟基烷基化合物反应。

  公开号：

  WO2015107110A1

文献信息

• [EN] CYANINE DYES AND THEIR CONJUGATES<br/>[FR] COLORANTS À BASE DE CYANINE ET LEURS CONJUGUÉS
  申请人：LI COR INC

  公开号：WO2012054749A1

  公开（公告）日：2012-04-26

  Compounds and methods are disclosed that are useful for noninvasive imaging in the near-infrared spectral range. The cyanine compounds of Formula (I), are presented: wherein Q is a portion of a polymethine bridge selected from the group consisting (Formula (X)). Also included are bioconjugates of the compounds of Formula (I), methods of labeling biomolecules with the compounds, and methods of imaging.

  揭示了用于近红外光谱范围内非侵入性成像的化合物和方法。所述的青菁化合物的化学式（I）如下所示：其中Q是从羧甲纶桥的一部分中选择的，所述羧甲纶桥选自以下群体（化学式（X））。还包括化合物的生物共轭物，用该化合物标记生物分子的方法，以及成像方法。
• Synthesis of 3′-O-(2-cyanoethyl)-2′-deoxythymidine-5′-phosphate as a model compound for evaluation of cyanoethyl cleavage
  作者：Angelika C. Keller、Saulius Serva、Diana C. Knapp、Marek Kwiatkowski、Joachim W. Engels

  DOI：10.1135/cccc2008183

  日期：——

  An essential and challenging task during the development of our sequencing-by-synthesis (SBS) technique is the evaluation of efficient cyanoethyl (CE) cleavage conditions. For this purpose 3′-O-(2-cyanoethyl)-2′-deoxythymidine-5′-phosphate as a model compound as well as a short DNA oligomer bearing the CE function as terminal group were synthesized and used for various deprotection experiments. As it is already known for 2′-O-CE-protected RNA oligonucleotides, the CE function can be cleaved with tetrabutylammonium fluoride (TBAF) in THF. Indeed, by using 3′-O-(2-cyanoethyl)-2′-deoxythymidine-5′-phosphate as a simple model compound for cleavage tests, we found out that the 3′-O-CE function is quantitatively cleaved with 1 M TBAF in THF. However, the CE group is also cleaved by other small bases like hydroxy groups under alkaline conditions. The CE cleavage with TBAF in THF gives the fastest and quantitative removal of the CE group under mild conditions for our sequencing-by-synthesis (SBS) application. The efficient removal of the 3′-CE group is crucial for the proof-of-principle of our SBS approach using dye-labeled 3′-CE-blocked dNTPs, which is currently under investigation. Herein we describe the application of 3′-O-(2-cyanoethyl)-2′-deoxythymidine-5′-phosphate as model compound for the development of reversible terminators for the SBS technique. Furthermore we suggest that nucleoside phosphates bearing any removable 3′-modification might be suitable model compounds for cleavage studies in a heterogeneous environment comparable to an oligonucleotide/ aprotic solvent system.

  在我们的合成-通过合成（SBS）技术开发过程中，一个重要且具有挑战性的任务是评估高效的氰乙基（CE）裂解条件。为此，我们合成了3'-O-(2-氰乙基)-2'-脱氧胸苷-5'-磷酸作为模型化合物，以及一个带有CE功能作为末端基团的短DNA寡聚体，并用于各种去保护实验。正如已经知道的对于2'-O-CE-保护的RNA寡核苷酸，CE功能可通过THF中的四丁基氟化铵（TBAF）来裂解。事实上，通过使用3'-O-(2-氰乙基)-2'-脱氧胸苷-5'-磷酸作为裂解试验的简单模型化合物，我们发现3'-O-CE功能在1 M TBAF/THF条件下可以被完全裂解。然而，CE基团也会在碱性条件下被其他小碱基如羟基裂解。在我们的合成-通过合成（SBS）应用中，CE裂解与TBAF/THF在温和条件下提供了最快和定量的CE基团去除。对3'-CE基团的高效去除对于使用染料标记的3'-CE阻断的dNTPs进行SBS方法的原理证明至关重要，目前正在进行研究。在这里，我们描述了3'-O-(2-氰乙基)-2'-脱氧胸苷-5'-磷酸作为合成-通过合成（SBS）技术的可逆终止子的开发的模型化合物的应用。此外，我们建议带有任何可去除的3'-修饰的核苷酸磷酸盐可能是适合的模型化合物，用于在类似寡核苷酸/无极性溶剂体系中进行裂解研究。
• Genetic control of predominantly error-free replication through an acrolein-derived minor-groove DNA adduct
  作者：Jung-Hoon Yoon、Richard P. Hodge、Linda C. Hackfeld、Jeseong Park、Jayati Roy Choudhury、Satya Prakash、Louise Prakash

  DOI：10.1074/jbc.ra117.000962

  日期：2018.2

  and it is a ubiquitous environmental pollutant. The reaction of acrolein with the N2 of guanine in DNA leads to the formation of γ-hydroxy-1-N2-propano-2' deoxyguanosine (γ-HOPdG), which can exist in DNA in a ring-closed or a ring-opened form. Here, we identified the translesion synthesis (TLS) DNA polymerases (Pols) that conduct replication through the permanently ring-opened reduced form of γ-HOPdG

  丙烯醛是一种 α,β-不饱和醛，是体内脂质过氧化和多胺代谢氧化的终产物，是一种普遍存在的环境污染物。丙烯醛与DNA中鸟嘌呤的N2反应生成γ-羟基-1-N2-丙烷-2'脱氧鸟苷（γ-HOPdG），它可以以闭环或开环形式存在于DNA中形式。在这里，我们鉴定了通过永久开环还原形式 γ-HOPdG（(r) γ-HOPdG）进行复制的跨损伤合成 (TLS) DNA 聚合酶 (Pols)，并表明通过这种加合物进行复制是通过 Rev1/分别为 Polη-、Polι/Polκ- 和 Polθ 依赖性通路。基于生化和结构研究，我们建议 Rev1 和 Polι 在加合物对面插入核苷酸 (nt) 以及 Pols η 和 κ 在从各自 TLS 途径中插入的 nt 扩展合成方面发挥作用。基于 Polθ 的遗传分析和生化研究，我们推断 Polθ 在 TLS 的 nt 插入和延伸步骤中的作用。纯化的 Rev1 和 Polθ
• Oligonucleotides containing 2'-0-modified purines
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US20040048826A1

  公开（公告）日：2004-03-11

  Novel 2′-O-alkyl guanosine compounds are provided. In accordance with preferred embodiments compounds having the structure: 1 wherein X is R 1 —(R 2 ) n ; R 1 is C 3 -C 20 alkyl, C 4 -C 20 alkenyl or C 2 -C 20 alkynyl; R 2 is halogen, hydroxyl, thiol, keto, carboxyl, nitro, nitroso, nitrile, trifluoromethyl, trifluoromethoxy, O-alkyl, S-alkyl, NH-alkyl, N-dialkyl, O-aryl, S-aryl, NH-aryl, O-aralkyl, S-aralkyl, NH-aralkyl, amino, N-phthalimido, imidazole, azido, hydrazino, hydroxylamino, isocyanato, sulfoxide, sulfone, sulfide, disulfide, silyl, aryl, heterocycle, carbocycle, intercalator, reporter molecule, conjugate, polyamine, polyamide, polyalkylene glycol, polyether, a group that enhances the pharmacodynamic properties of oligonucleotides, or a group that enhances the pharmacokinetic properties of oligonucleotides; and n is an integer from 0 to about 6, are provided.

  本发明提供了新型的2'-O-烷基鸟苷化合物。根据优选实施例，所提供的化合物具有以下结构：1其中X为R1-(R2)n；R1为C3-C20烷基、C4-C20烯基或C2-C20炔基；R2为卤素、羟基、硫醇、酮、羧基、硝基、亚硝基、腈、三氟甲基、三氟甲氧基、O-烷基、S-烷基、NH-烷基、N-二烷基、O-芳基、S-芳基、NH-芳基、O-芳基烷基、S-芳基烷基、NH-芳基烷基、氨基、N-邻苯二甲酰亚胺基、咪唑基、叠氮基、肼基、羟胺基、异氰酸酯基、亚砜基、磺酰基、硫醚基、二硫化物基、硅烷基、芳基、杂环、碳环、插入剂、报告分子、共轭物、多胺、多酰胺、多烷基氧基、多醚、增强寡核苷酸药效学性质的基团或增强寡核苷酸药代动力学性质的基团；n为0到约6的整数。
• COMBINATORIAL LIBRARY, A METHOD FOR PREPARATION OF THAT COMBINATORIAL LIBRARY, A METHOD FOR SEQUENCE IDENTIFICATION, A METHOD FOR SEQUENCING THE ELEMENTS OF COMBINATORIAL LIBRARIES OF OLIGONUCLEOTIDES AND/OR OLIGONUCLEOTIDE ANALOGUES, THE USE OF A LINKER TO GENERATE COMBINATORIAL LIBRARIES AND A SEQUENCE IDENTIFICATION SET
  申请人：Markiewicz Wojciech T.

  公开号：US20130053258A1

  公开（公告）日：2013-02-28

  The invention provides a combinatorial library, a method for preparation of that combinatorial library, a method for sequence identification, a method for sequencing the elements of combinatorial libraries of oligonucleotides and/or oligonucleotide analogues, the use of a linker to generate combinatorial libraries and a sequence identification set. More precisely, the objective of the invention is the ability to “read” sequences of selected elements of combinatorial libraries of freely modified synthetic oligonucleotides. The solution may be used both for researching for leading compounds in the pharmaceutical industry, and as a tool for studying the properties of oligonucleotides in the aspect of their potential use in experimental antisense or antigen therapy. The invention develops an appropriate strategy for determining the structure of isolated library elements, as usefulness of the combinatorial library depends on the ability to recognize the structure of its elements. Thanks to the developed and presented method for sequencing combinatorial oligonucleotide libraries it is possible to indisputably identify the sequences of biologically active elements selected by the combinatorial synthesis method.

  本发明提供了一种组合式库、制备该组合式库的方法、序列鉴定的方法、测序寡核苷酸和/或寡核苷酸类似物组合式库元素的方法、使用连接物生成组合式库和序列鉴定集的方法。更具体地说，本发明的目的是能够“读取”自由修饰合成寡核苷酸组合式库中所选元素的序列。该解决方案既可用于药物行业中寻找领先化合物的研究，也可作为研究寡核苷酸在实验性反义或抗原治疗方面潜在用途的工具。本发明开发了一种适当的策略，用于确定分离的库元素的结构，因为组合式库的有用性取决于识别其元素结构的能力。由于开发和提出了组合式寡核苷酸库测序的方法，因此可以毫无疑问地确定通过组合合成方法选择的生物活性元素的序列。