4-amino-1-[(2-O-propargyl)-β-D-ribofuranosyl]-2H-pyrimidin-2-one | 206552-85-4

• 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: 4-amino-1-[(2-O-propargyl)-β-D-ribofuranosyl]-2H-pyrimidin-2-one
• 英文别名: 2’-O-propargyl-cytidine；2'-O-propargyl cytidine；2'-O-propargyl-cytidine；2'-o-Propargylcytidine；4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-ynoxyoxolan-2-yl]pyrimidin-2-one
• CAS: 206552-85-4
• 化学式: C₁₂H₁₅N₃O₅
• 分子量: 281.268
• InChiKey: FJGRSBJPLPTKDE-QCNRFFRDSA-N

物化性质

• 沸点：
  544.7±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  20
• 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：
  118
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-1-[(2-O-propargyl)-β-D-ribofuranosyl]-2H-pyrimidin-2-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.33h， 生成 2’-O-propargyl-5’-dimethoxytrityl-N⁴-acetyl-cytidine
  参考文献：
  名称：

  Chemical Synthesis of Mono- and Bis-Labeled Pre-MicroRNAs

  摘要：

  DOI：

  10.1002/anie.201304986
• 作为产物：
  描述：

  2’-O-propargyl-N⁴-acetyl-cytidine 在 氨 作用下， 以 乙腈 为溶剂， 生成 4-amino-1-[(2-O-propargyl)-β-D-ribofuranosyl]-2H-pyrimidin-2-one
  参考文献：
  名称：

  CN111875646

  摘要：

  公开号：

文献信息

• Parallel Stranded DNA Stabilized with Internal Sugar Cross-Links: Synthesis and Click Ligation of Oligonucleotides Containing 2′-Propargylated Isoguanosine
  作者：Suresh S. Pujari、Frank Seela

  DOI：10.1021/jo4012706

  日期：2013.9.6

  solid-phase synthesis. A series of oligo-2′-deoxyribonucleotides with parallel (ps) and antiparallel (aps) strand orientation were constructed containing isoguanine-cytosine, isoguanine-isocytosine, and adenine-thymine base pairs. Complementary oligonucleotides with propargylated sugar residues were ligated in a stepwise manner with a chelating bis-azide under copper catalysis. Cross-links were introduced within

  内部糖交联首次通过点击连接引入具有平行链取向的寡核苷酸中。为此，用可点击的炔丙基残基将异鸟苷核糖部分的2'-或3'-位置官能化，并且显着改善了炔丙基化胞嘧啶结构单元的合成。制备亚磷酰胺并用于固相合成。构建了具有平行（ps）和反平行（aps）链取向的一系列寡2'-脱氧核糖核苷酸，其包含异鸟嘌呤-胞嘧啶，异鸟嘌呤-异胞嘧啶和腺嘌呤-胸腺嘧啶碱基对。在铜催化下，将具有炔丙基化糖残基的互补寡核苷酸与螯合双叠氮化物逐步连接。交联被引入一个碱基对内或被两个碱基对隔开的位置。从T m稳定性研究表明，交联可稳定地稳定具有平行链取向的DNA（ΔT m从+16到+18.5°C），其增加幅度与aps DNA相似。
• COMPOSITIONS CONTAINING NUCLEIC ACID NANOPARTICLES WITH MODULAR FUNCTIONALITY
  申请人：Sixfold Bioscience Ltd.

  公开号：US20210330810A1

  公开（公告）日：2021-10-28

  The invention provides compositions containing cargo molecules attached to elements that improve the function of the cargo molecules in the body of a subject. The compositions are useful for therapeutic and diagnostic purposes. Furthermore, the invention outlines ways in which these compositions can be produced; the core molecule can be functionalized, via bioorthogonal click chemistry, in such a way as to impart modular characteristics. This functionalization simultaneously allows for loading of biologically relevant cargo and provides stabilization to the overall structure of the molecule.

  本发明提供了一种包含附着于能够改善受试者体内载荷分子功能的元素的组合物。该组合物在治疗和诊断方面具有用途。此外，本发明还概述了可生产这些组合物的方法；核心分子可以通过生物正交点击化学功能化，以赋予模块化特性。这种功能化同时允许装载生物相关载荷并为分子的整体结构提供稳定性。
• Synthesis of 2′-<i>O</i>-Propargyl Nucleoside Triphosphates for Enzymatic Oligonucleotide Preparation and “Click” Modification of DNA with Nile Red as Fluorescent Probe
  作者：Ulrike Wenge、Thomas Ehrenschwender、Hans-Achim Wagenknecht

  DOI：10.1021/bc300624m

  日期：2013.3.20

  Uridine, adenosine, guanosine, and cytidine that carry a propargyl group attached to the 2′-oxygen were converted efficiently to the corresponding nucleoside triphosphates (pNTPs). Primer extension experiments revealed that pUTP, pATP, and pGTP can be successfully incorporated in oligonucleotides in the so-called 9°N and Therminator DNA polymerases. Most importantly, the ethynyl group as single 2′-modification

  带有与2'-氧连接的炔丙基的尿苷，腺苷，鸟苷和胞苷被有效地转化为相应的核苷三磷酸（pNTPs）。引物延伸实验表明，pUTP，pATP和pGTP可以成功地掺入所谓的9°N和Therminator DNA聚合酶的寡核苷酸中。最重要的是，作为酶法制备的寡核苷酸的单个2'-修饰的乙炔基可用于合成后标记。荧光尼罗红叠氮化物在“点击”型环加成反应后，通过PAGE分析代表性地表明了这一点。这些结果表明，作为寡核苷酸中最重要的修饰位点之一的2'-位置现在不仅可用于合成，而且可用于酶促寡核苷酸制备。
• Metal free, “click and click–click” conjugation of ribonucleosides and 2′-OMe oligoribonucleotides on the solid phase
  作者：Ishwar Singh、Frances Heaney

  DOI：10.1039/b918463e

  日期：——

  A fast and practical metal free conjugation of ribonucleosides and 2′-OMe 4-mer oligoribonucleotides has been accomplished by a nitrile oxide alkyne click cycloaddition reaction on the solid-phase, the methodology is suited to modification at either, or both, the 3′- or the 5′-terminus of the oligoribonucleotide substrate.

  通过在固相上进行腈氧化炔烃点击环化反应，实现了核糖核苷和 2-OMe 4-mer 寡核苷酸的快速、实用的无金属共轭，该方法适用于寡核苷酸底物的 3-²- 或 5-²- 端部的修饰。
• Novel nucleoside and oligonucleotide analogues
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20020147332A1

  公开（公告）日：2002-10-10

  A compound of the formula (1): 1 wherein R 1 and R 2 are the same or different and represent a hydrogen atom, a hydroxyl protecting group, a phosphate group, or —P(R 3 )R 4 , wherein R 3 and R 4 are the same or different and represent a hydroxyl group, an amino group, an alkoxy group having from 1 to 4 carbon atoms, a cyanoalkoxy group having from 1 to 5 carbon atoms or an amino group substituted by an alkyl group having from 1 to 4 carbon atoms; A represents an alkylene group having from 1 to 4 carbon atoms and B represents a purin-9-yl group, a 2-oxo-pyrimidin-1-yl group, a substituted purin-9-yl group or a substituted 2-oxo-pyrimidin-1-yl group having a substituent &agr; selected from the group consisting of a hydroxyl group which may be protected, an alkoxy group having from 1 to 4 carbon atoms, a mercapto group which may be protected, an alkylthio group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, an amino group which may be protected, a mono- or di-alkylamino group which may be substituted by an alkyl group having from 1 to 4 carbon atoms, an alkyl group having from 1 to 4 carbon atoms and a halogen atom; or a salt thereof.

  化合物的式子（1）：1其中R1和R2相同或不同，表示氢原子，羟基保护基，磷酸基或-P（R3）R4，其中R3和R4相同或不同，表示羟基，氨基，具有1至4个碳原子的烷氧基，具有1至5个碳原子的氰基烷氧基或被1至4个碳原子的烷基取代的氨基; A表示具有1至4个碳原子的烷基，B表示嘌呤-9-基，2-氧代嘧啶-1-基，取代的嘌呤-9-基或取代的2-氧代嘧啶-1-基，具有α取代基，所述α取代基选自羟基（可能被保护），具有1至4个碳原子的烷氧基，巯基（可能被保护），具有1至4个碳原子的烷硫基，具有1至4个碳原子的烷氧基，氨基（可能被保护），可以被1至4个碳原子的烷基取代的单烷基或双烷基氨基，具有1至4个碳原子的烷基和卤原子; 或其盐。