2'-O-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2'-O-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine
• 英文别名: 2′-O-benzoyl-5′-O-(4,4′-dimethoxytrityl)-2′,3′-secouridine；2'-O-Benzoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine；[(2R)-2-[(2S)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-3-hydroxypropan-2-yl]oxy-2-(2,4-dioxopyrimidin-1-yl)ethyl] benzoate
• 化学式: C₃₇H₃₆N₂O₉
• 分子量: 652.701
• InChiKey: INQCHBJFCVVVIU-UZNNEEJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-O-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine 在 吡啶 、 水 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 21.5h， 生成 3′-O-tert-butyldimethylsilyl-5′-O-(4,4′-dimethoxytrityl)-2′,3′-secouridine
  参考文献：
  名称：

  [EN] NUCLEIC ACID-POLYPEPTIDE COMPOSITIONS AND USES THEREOF
  [FR] COMPOSITIONS D'ACIDE NUCLÉIQUE-POLYPEPTIDE ET UTILISATIONS DE CELLES-CI

  摘要：

  本文披露了包含与修饰的多核苷酸分子和聚合物结合基团的组合物和药物配方。本文还描述了利用包含与多核苷酸分子和聚合物结合基团共轭的组合物或药物配方治疗癌症的方法。

  公开号：

  WO2019071028A1
• 作为产物：
  描述：

  5’-O-(4,4’-二甲氧基三苯甲基)尿苷 在 sodium tetrahydroborate 、 sodium periodate 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 2'-O-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine
  参考文献：
  名称：

  [EN] UNA AMIDITES AND USES THEREOF
  [FR] AMIDITES D'UNA ET LEURS UTILISATIONS

  摘要：

  本文披露了包含结合基团与修饰的多核苷酸分子和聚合物结合的组合物和药物配方。本文还描述了利用包含结合基团与多核苷酸分子和聚合物结合的组合物或药物配方进行治疗疾病的方法。

  公开号：

  WO2020247818A1

文献信息

• Synthesis of an Unlocked Nucleic Acid Terpyridine Monomer and Binding of Divalent Metal Ion in Nucleic Acid Duplexes
  作者：Kasper K. Karlsen、Troels B. Jensen、Jesper Wengel

  DOI：10.1021/jo9019978

  日期：2009.11.20

  Herein we present the synthesis and thermal stability studies of modified oligonucleotides containing an unlocked nucleic acid (UNA) terpyridine monomer. Incorporation of this monomer into both strands of a DNA duplex allowed reversible thermal stability modulation upon addition or withdrawal of divalent metal ions. A likely explanation of this phenomenon is interstrand complexation between two terpyridine

  本文中，我们介绍了含有解锁核酸（UNA）吡啶吡啶单体的修饰寡核苷酸的合成和热稳定性研究。将该单体掺入DNA双链体的两条链中，可在添加或撤出二价金属离子时进行可逆的热稳定性调节。这种现象的可能解释是两个三联吡啶单元与金属离子之间的链间络合。该系统可用于基于DNA杂交的纳米级设备的开发。
• 3′-Pyrene-modified unlocked nucleic acids: synthesis, fluorescence properties and a surprising stabilization effect on duplexes and triplexes
  作者：Maria Ejlersen、Niels Langkjær、Jesper Wengel

  DOI：10.1039/c6ob02773c

  日期：——

  times into 21-mer DNA and 2′-O-Me-RNA ONs. Duplex melting temperatures, circular dichroism (CD) spectra, steady-state fluorescence emission spectra, UV/Vis absorption spectra and triplex melting temperatures were measured for the modified duplexes. The presence of the pyrene-modified UNA monomer lead to a surprising and unprecedented thermal stabilization of especially DNA:DNA duplexes when compared to

  开发了一种新的3' - O-氨基-UNA单体的高效合成物，作为进一步功能化和掺入寡核苷酸（ONs）的支架。将21官能化的3'- O-氨基-UNA掺入21-mer DNA和2'- O中一次，两次或三次-Me-RNA ON。测量了修饰双链体的双链体熔化温度，圆二色性（CD）光谱，稳态荧光发射光谱，UV / Vis吸收光谱和三重链熔化温度。与相应的未修饰的DNA：DNA双链体相比，the修饰的UNA单体的存在导致特别是DNA：DNA双链体出乎意料且前所未有的热稳定性。对于某些修饰的双链体，还发现了改善的错配辨别力。CD光谱显示修饰的和未修饰的双链体之间没有主要差异。分子建模表明，通过CD和UV / Vis吸收研究证实，pyr部分位于DNA：DNA双链体的小沟中。在单链ON中多次掺入单体后，稳态荧光发射研究揭示了exc准分子的形成，在大多数情况下，该准分子在双链杂交后被淬灭，并且在某些修饰的链结构
• UNA (unlocked nucleic acid): A flexible RNA mimic that allows engineering of nucleic acid duplex stability
  作者：Niels Langkjær、Anna Pasternak、Jesper Wengel

  DOI：10.1016/j.bmc.2009.06.045

  日期：2009.8

  UNA (unlocked nucleic acid) monomers are acyclic derivatives of RNA lacking the C2′–C3′-bond of the ribose ring of RNA. Synthesis of phosphoramidite UNA building blocks of the nucleobases adenine, cytosine, guanine, and uracil is described herein together with their incorporation into RNA strands. UNA monomers additively decrease nucleic acid duplex stability and can be positioned strategically to

  UNA（未锁定核酸）单体是RNA的无环衍生物，缺少RNA核糖环的C2'–C3'键。本文描述了亚核苷腺嘌呤，胞嘧啶，鸟嘌呤和尿嘧啶的亚磷酰胺UNA构件的合成以及它们掺入RNA链的过程。UNA单体会额外地降低核酸双链体的稳定性，并且可以在战略上进行定位，以诱导缺乏对错配的歧视，即通用碱基行为，或对错配的歧视，即提高的杂交特异性。通过CD光谱法显示，UNA修饰的RNA双链体在结构上模仿未修饰的RNA双链体。
• HYDROXYMETHYL SUBSTITUTED RNA OLIGONUCLEOTIDES AND RNA COMPLEXES
  申请人：Wengel Jesper

  公开号：US20100056768A1

  公开（公告）日：2010-03-04

  The present invention is directed to RNA oligonucleotides or complexes of RNA oligonucleotides, denoted herein together as RNA complexes, containing at least one, but optionally more that one, hydroxymethyl substituted nucleotide monomer(s). By a hydroxymethyl substituted nucleotide monomer is understood a nucleotide monomer containing a hydroxymethyl group (that may be unsubstituted, O-substituted for example with a conjugating group, or converted into an optionally substituted or conjugated aminomethyl group). This hydroxymethyl group is not partaking in formation of an internucleotide linkage and is not the hydroxymethyl group (containing the 5′-hydroxy group) of a natural RNA monomer. The RNA complexes of the invention may be useful for therapeutic applications, diagnostic applications or research applications. The complexes include short interfering RNA complexes (siRNA duplexes) comprising an antisense strand and a continued or a discontinued passenger strand (“sense strand”) capable of regulating gene expression. At least one of these strands, possible more than one of these strands, are modified with one or more hydroxymethyl substituted nucleotide monomer(s) of this invention, that can be positioned at the 3′-end, at the 5′-end or internally. The RNA complexes of the invention can also be single stranded RNA oligonucleotides (“RNA strands”) that are modified with at least one, but optionally more that one, hydroxymethyl substituted nucleotide monomer(s). Such single stranded RNA strands are to be considered included whenever the term RNA complexes is used in this patent application. The complexes of the invention display enhanced stability towards nucleolytic degradation relative to the corresponding complexes comprised entirely from natural RNA monomers.

  本发明涉及RNA寡核苷酸或RNA寡核苷酸复合物，统称为RNA复合物，其中至少含有一个，但可选地含有多个羟甲基取代的核苷酸单体。羟甲基取代的核苷酸单体是指含有羟甲基基团（可以是未取代的，例如与共轭基取代的O-取代的，或者转化为可选取代或共轭的氨甲基基团）的核苷酸单体。该羟甲基基团不参与核苷酸之间的连接形成，并且不是天然RNA单体中含有5'-羟基基团的羟甲基基团。本发明的RNA复合物可用于治疗应用、诊断应用或研究应用。这些复合物包括短干扰RNA复合物（siRNA双链体），包括一个反义链和一个持续或中断的载体链（“正义链”），能够调节基因表达。这些链中至少有一条，可能有多条，被本发明的一个或多个羟甲基取代的核苷酸单体修饰，可以位于3'-端、5'-端或内部。本发明的RNA复合物还可以是单链RNA寡核苷酸（“RNA链”），其中至少含有一个，但可选地含有多个羟甲基取代的核苷酸单体。只要在本专利申请中使用了“RNA复合物”一词，就应该包括这样的单链RNA链。与完全由天然RNA单体组成的相应复合物相比，本发明的复合物表现出对核酸酶降解的增强稳定性。
• Hydroxymethyl substituted RNA oligonucleotides and RNA complexes
  申请人：Marina Biotech, Inc.

  公开号：US08314227B2

  公开（公告）日：2012-11-20

  The present invention is directed to RNA oligonucleotides or complexes of RNA oligonucleotides, denoted herein together as RNA complexes, containing at least one, but optionally more that one, hydroxymethyl substituted nucleotide monomer(s). By a hydroxymethyl substituted nucleotide monomer is understood a nucleotide monomer containing a hydroxymethyl group (that may be unsubstituted, O-substituted for example with a conjugating group, or converted into an optionally substituted or conjugated aminomethyl group). This hydroxymethyl group is not partaking in formation of an internucleotide linkage and is not the hydroxymethyl group (containing the 5′-hydroxy group) of a natural RNA monomer. The RNA complexes of the invention may be useful for therapeutic applications, diagnostic applications or research applications.

  本发明涉及RNA寡核苷酸或RNA寡核苷酸复合物，统称为RNA复合物，其中至少含有一个，但可选地含有多个羟甲基取代核苷酸单体。羟甲基取代核苷酸单体是指含有羟甲基基团（可以是未取代的，例如与共轭基团O取代的，或转化为可选的取代或共轭氨甲基基团）。该羟甲基基团不参与核苷酸单体之间的连接形成，也不是天然RNA单体中含有5'-羟基基团的羟甲基基团。本发明的RNA复合物可能对治疗应用、诊断应用或研究应用有用。