N-乙酰基-5’-O-(4,4-二甲氧基三苯甲基)-2’-O-甲基胞苷-3’-(2-氰基乙基-N,N-二异丙基)亚磷酰胺 | 199593-09-4

• 物质功能分类: 生物化工 - 生化试剂 - 其他生化试剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: N-乙酰基-5’-O-(4,4-二甲氧基三苯甲基)-2’-O-甲基胞苷-3’-(2-氰基乙基-N,N-二异丙基)亚磷酰胺
• 中文别名: N-乙酰基-5'-O-(4,4-二甲氧基三苯甲基)-2'-O-甲基胞苷-3'-(2-氰基乙基-N,N-二异丙基)亚磷酰胺；2'-OMe-Ac-C亚磷酰胺单体；N-乙酰基-5`-O-(4,4-二甲氧基三苯甲基)-2`-O-甲基胞苷-3`-(2-氰基乙基-N,N-二异丙基)亚磷酰胺；2'-OME-AC-C亚磷酰胺单体；2-O-ME-RC(AC)亚磷酰胺单体
• 英文名称: 2'-OMe-Ac-C Phosphoramidite
• 英文别名: N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-methoxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 199593-09-4；213020-84-9；213020-85-0
• 化学式: C₄₂H₅₂N₅O₉P
• 分子量: 801.877
• InChiKey: WNWUMIPFLOKTEZ-UAQIPLLRSA-N

物化性质

• 熔点：
  102 - 104°C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29349990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-乙酰基-5’-O-(4,4-二甲氧基三苯甲基)-2’-O-甲基胞苷-3’-(2-氰基乙基-N,N-二异丙基)亚磷酰胺 在 甲胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到5'-O-dimethoxytritil-2'-O-methylcytidine-3'-O-(2-cianoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  O-Selective Condensation Using P−N Bond Cleavage in RNA Synthesis without Base Protection

  摘要：

  In RNA synthesis without base protection, a new method for O-selective condensation with more than 99% selectivity was developed by 6-nitro-HOBt-mediated cleavage of undesired P(III)-N bonds on nucleobase moieties. Moreover, we for the first time succeeded in synthesizing oligoRNAs without base protection.

  DOI：

  10.1021/ol800911b
• 作为产物：
  描述：

  N-乙酰基-2'-O-甲基胞苷 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-乙酰基-5’-O-(4,4-二甲氧基三苯甲基)-2’-O-甲基胞苷-3’-(2-氰基乙基-N,N-二异丙基)亚磷酰胺
  参考文献：
  名称：

  Ultrafast Cleavage and Deprotection of Oligonucleotides Synthesis and Use of C^AcDerivatives

  摘要：

  We have investigated the use of alkylamines as fast cleavage and deprotection reagents for the solid phase synthesis of oligonucleotides and found methylamine/ammonium hydroxide (or methylamine) as an efficient reagent. The transamination side product formed with the commonly used dC(bz) has been eliminated by the use of dC(Ac) phosphoramidite. This system has successfully been used in the synthesis of oligonucleotides and oligonucleoside phosphorothioates. DMT dC(Ac) hydrogen phosphonate and DMT ribo C-Ac-2'-OMe phosphoramidite also have been prepared and used in the synthesis of oligonucleotides.

  DOI：

  10.1080/07328319708006236

文献信息

• MODIFIED DOUBLE-STRANDED POLYNUCLEOTIDE
  申请人：Koizumi Makoto

  公开号：US20120220649A1

  公开（公告）日：2012-08-30

  The present invention provides a double-stranded polynucleotide having a sense strand polynucleotide consisting of a nucleotide sequence complementary to a target sequence in a target gene, and an antisense strand polynucleotide having a nucleotide sequence complementary to the sense strand polynucleotide, wherein an aryl or heteroaryl compound is bound to a phosphate group at the 5′-end of the antisense strand polynucleotide.

  本发明提供了一种双链聚核苷酸，其具有一个具有与目标基因中的目标序列互补的核苷酸序列的正链聚核苷酸，以及一个具有与正链聚核苷酸互补的核苷酸序列的反义链聚核苷酸，其中一种芳基或杂环芳基化合物结合到反义链聚核苷酸的5'-末端的磷酸基团上。
• Modified Single-Stranded Polynucleotide
  申请人：Koizumi Makoto

  公开号：US20130253038A1

  公开（公告）日：2013-09-26

  It is intended to provide a polynucleotide that is resistant to RNase and has an RNA interference effect, etc. The present invention provides a single-stranded polynucleotide that is derived from a double-stranded polynucleotide comprising a sense strand polynucleotide corresponding to a target gene, and an antisense strand polynucleotide having a nucleotide sequence complementary to the sense strand polynucleotide, and has a structure in which the 5′-end of the antisense strand and the 3′-end of the sense strand are linked via a phenyl group-containing linker to form a phosphodiester structure at each of these ends.

  本发明旨在提供一种对RNase具有抗性并具有RNA干扰效应的多核苷酸。本发明提供了一种单链多核苷酸，其源自于包含与目标基因相对应的正义链多核苷酸和具有与正义链多核苷酸互补的核苷酸序列的反义链多核苷酸的双链多核苷酸，且具有一种结构，其中反义链的5'-末端和正义链的3'-末端通过含苯基的连接剂连接形成磷酸二酯结构。
• iRNA agents targeting VEGF
  申请人：Alnylam Pharmaceuticals, Inc.

  公开号：EP2365077A1

  公开（公告）日：2011-09-14

  The features of the present invention relate to compounds, compositions and methods useful for modulating the expression of vascular endothelial growth factor (VEGF), such as by the mechanism of RNA interference (RNAi). The compounds and compositions include iRNA agents that can be unmodified or chemically modified.

  本发明的特征涉及用于调节血管内皮生长因子（VEGF）表达的化合物、组合物和方法，例如通过 RNA 干扰（RNAi）机制。这些化合物和组合物包括可未经修饰或经化学修饰的 iRNA 制剂。
• MODIFIED SINGLE-STRAND POLYNUCLEOTIDE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2647713A1

  公开（公告）日：2013-10-09

  It is intended to provide a polynucleotide that is resistant to RNase and has an RNA interference effect, etc. The present invention provides a single-stranded polynucleotide that is derived from a double-stranded polynucleotide comprising a sense strand polynucleotide corresponding to a target gene, and an antisense strand polynucleotide having a nucleotide sequence complementary to the sense strand polynucleotide, and has a structure in which the 5'-end of the antisense strand and the 3'-end of the sense strand are linked via a phenyl group-containing linker to form a phosphodiester structure at each of these ends.

  本发明旨在提供一种能抗 RNase 并具有 RNA 干扰作用的多核苷酸等。本发明提供了一种由双链多核苷酸衍生的单链多核苷酸，双链多核苷酸包括与靶基因相对应的有义链多核苷酸和具有与有义链多核苷酸互补的核苷酸序列的反义链多核苷酸、其结构是反义链的 5'-端和有义链的 3'-端通过含苯基的连接体连接，在这两端分别形成磷酸二酯结构。
• IRNA agents targeting VEGF
  申请人：Fougerolles De Antonin

  公开号：US20060223770A1

  公开（公告）日：2006-10-05

  The features of the present invention relate to compounds, compositions and methods useful for modulating the expression of vascular endothelial growth factor (VEGF), such as by the mechanism of RNA interference (RNAi). The compounds and compositions include iRNA agents that can be unmodified or chemically-modified.

  本发明的特征涉及用于调节血管内皮生长因子（VEGF）表达的化合物、组合物和方法，例如通过 RNA 干扰（RNAi）机制。本发明的化合物和组合物包括未经修饰或化学修饰的 iRNA 制剂。