1-(2’-O,4-C-甲桥-BETA-D-呋喃核糖基)尿苷 | 200435-92-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2’-O,4-C-甲桥-BETA-D-呋喃核糖基)尿苷
• 中文别名: 1-(2'-O,4-C-甲桥-BETA-D-呋喃核糖基)尿苷；1-(2-O,4-C-甲桥-beta-D-呋喃核糖基)尿嘧啶核苷；1-(2'-O,4-C-甲桥-BETA-D-呋喃核糖基)尿嘧啶核苷；1-(2'-O,4-C-甲桥-beta-D-呋喃核糖基)尿嘧啶核苷
• 英文名称: 2'-O,4'-C-methyleneuridine
• 英文别名: 1-((1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione；1-[(1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]pyrimidine-2,4-dione
• CAS: 200435-92-3
• 化学式: C₁₀H₁₂N₂O₆
• 分子量: 256.215
• InChiKey: KNLNWXXWKDEEFW-JIOCBJNQSA-N

物化性质

• 熔点：
  239-243 °C(Solv: methanol (67-56-1))
• 密度：
  1.695
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

制备方法与用途

生物活性方面，2′-O,4′-C-甲基乌苷（化合物15a）是一种双环核苷。

反应信息

• 作为反应物：
  描述：

  1-(2’-O,4-C-甲桥-BETA-D-呋喃核糖基)尿苷 在 吡啶 、 4-二甲氨基吡啶 、 硫酸氢铵 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 127.0h， 生成 1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA)

  摘要：

  For development of ideal antisense and antigene molecules, various chemical modifications of oligonucleotides have been studied. However, despite their importance. there is only limited information available on the tripler-forming ability of the conformationally restricted or locked oligonucleotides. We report herein that 2'-O,4'-C-methylene bridged nucleic acid (2',4'-BNA) modification of tripler-forming oligonucleotide: (TFO) significantly enhances the binding affinity towards target dsDNA. On T, measurements. the triplex with the 2',4'-BNA oligonucleotides were found to be stabilized with DeltaT(m)/modification of +4.3 to + 5 degreesC at pH 6.6 compared to the triplexes with the unmodified oligonucleotide. By means of gel-retardation assay, the binding constant of the 2'.4'-BNA oligonucleotide at pH 7.0 was at least 300-fold higher than that of the natural oligonucleotide. In addition, the 2',4'-BNA oligonucleotide clearly showed the inhibition of the NF-K-B transcription factor (p50)-target dsDNA binding by forming a stable tripler at pH 7.0. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00325-4
• 作为产物：
  描述：

  2',3'-O-benzylidene-4'-(p-toluenesulfonyloxymethyl)uridine 在 palladium on activated charcoal 氢气 、 sodium hexamethyldisilazane 、 四氯化钛 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 33.0h， 生成 1-(2’-O,4-C-甲桥-BETA-D-呋喃核糖基)尿苷
  参考文献：
  名称：

  2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA)

  摘要：

  For development of ideal antisense and antigene molecules, various chemical modifications of oligonucleotides have been studied. However, despite their importance. there is only limited information available on the tripler-forming ability of the conformationally restricted or locked oligonucleotides. We report herein that 2'-O,4'-C-methylene bridged nucleic acid (2',4'-BNA) modification of tripler-forming oligonucleotide: (TFO) significantly enhances the binding affinity towards target dsDNA. On T, measurements. the triplex with the 2',4'-BNA oligonucleotides were found to be stabilized with DeltaT(m)/modification of +4.3 to + 5 degreesC at pH 6.6 compared to the triplexes with the unmodified oligonucleotide. By means of gel-retardation assay, the binding constant of the 2'.4'-BNA oligonucleotide at pH 7.0 was at least 300-fold higher than that of the natural oligonucleotide. In addition, the 2',4'-BNA oligonucleotide clearly showed the inhibition of the NF-K-B transcription factor (p50)-target dsDNA binding by forming a stable tripler at pH 7.0. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00325-4

文献信息

• LNA (Locked Nucleic Acids): Synthesis of the adenine, cytosine, guanine, 5-methylcytosine, thymine and uracil bicyclonucleoside monomers, oligomerisation, and unprecedented nucleic acid recognition
  作者：Alexei A. Koshkin、Sanjay K. Singh、Poul Nielsen、Vivek K. Rajwanshi、Ravindra Kumar、Michael Meldgaard、Carl Erik Olsen、Jesper Wengel

  DOI：10.1016/s0040-4020(98)00094-5

  日期：1998.4

  LNA (Locked Nucleic Acids), consisting of 2′-O,4′-C-methylene bicyclonucleoside monomers, is efficiently synthesized and its nucleic acid recognition potential evaluated for six different nucleobases, namely adenine, cytosine, guanine, 5-methylcytosine, thymine and uracil. Unprecedented increases (+3 to +8 °C per modification) in the thermal stability of duplexes towards both DNA and RNA were obtained

  由2'- O，4'- C-亚甲基双环核苷单体组成的LNA（锁定核酸）被有效合成，并评估了其对六种不同核碱基（腺嘌呤，胞嘧啶，鸟嘌呤，5-甲基胞嘧啶，胸腺嘧啶）的核酸识别潜力和尿嘧啶。当评估部分或完全修饰的LNA的混合序列时，双链体对DNA和RNA的热稳定性出现了前所未有的提高（每个修饰+3至+8°C）。错配序列的研究表明，与相应的未修饰参考链相比，LNA遵循具有普遍提高的选择性的Watson-Crick碱基配对规则。
• REAGENTS AND METHODS FOR REPLICATION, TRANSCRIPTION, AND TRANSLATION IN SEMI-SYNTHETIC ORGANISMS
  申请人：The Scripps Research Institute

  公开号：US20200392550A1

  公开（公告）日：2020-12-17

  Disclosed herein are compositions, methods, cells, engineered microorganisms, and kits for increasing the production of proteins or polypeptides comprising one or more unnatural amino acids. Further provided are compositions, cells, engineered microorganisms, and kits for increasing the retention of unnatural nucleic acids encoding the unnatural amino acids in an engineered cell, or semi-synthetic organism.

  本文揭示了一种用于增加含有一个或多个非天然氨基酸的蛋白质或多肽的生产的组合物、方法、细胞、工程微生物和试剂盒。此外，还提供了一种用于增加编码非天然氨基酸的非天然核酸在工程细胞或半合成生物体中的保留的组合物、细胞、工程微生物和试剂盒。
• Novel bicyclonucleoside and oligonucleotide analogue
  申请人：Takeshi IMANISHI

  公开号：US20030105309A1

  公开（公告）日：2003-06-05

  An oligo- or polynucleotide analogue having one or more structures of the general formula 1 where B is a pyrimidine or purine nucleic acid base, or an analogue thereof, is disclosed. The use of this analogue provides an oligonucleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.

  揭示了一种具有通式1的寡核苷酸或多核苷酸类似物，其中B是嘧啶或嘌呤核酸碱基，或其类似物。该类似物的使用提供了一种寡核苷酸类似物反义分子，在体内具有最小的水解能力，具有高的sense链结合能力，并且易于合成。
• Bicyclonucleoside and oligonucleotide analogues
  申请人：Takeshi Imanishi

  公开号：US06268490B1

  公开（公告）日：2001-07-31

  An oligo- or polynucleotide analogue having one or more structures of the general formula where B is a pyrimidine or purine nucleic acid base, or an analogue thereof, is disclosed. The use of this analogue provides an oligonucleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.

  揭示了一种具有一种或多种一般公式的结构的寡核苷酸或多核苷酸类似物，其中B是嘧啶或嘌呤核酸碱基或其类似物。该类似物的使用提供了一种寡核苷酸类似物反义分子，其在体内具有最小的水解能力，具有高的sense链结合能力，并且易于合成。
• Bicyclonucleoside and oligonucleotide analogue
  申请人：Imanishi Takeshi

  公开号：US06770748B2

  公开（公告）日：2004-08-03

  An oligo- or polynucleotide analogue having one or more structures of the general formula where B is a pyrimidine or purine nucleic acid base, or an analogue thereof, is disclosed. The use of this analogue provides an oligonucleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.

  揭示了一种具有一种或多种通式结构的寡核苷酸或多核苷酸类似物，其中B是嘧啶或嘌呤核酸碱基，或其类似物。使用这种类似物提供了一种寡核苷酸类似物反义分子，该分子在体内具有最小的水解能力，具有高的sense链结合能力，并且易于合成。