3'-O-benzyl-4'-(p-toluenesulfonyloxymethyl)uridine | 200435-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-O-benzyl-4'-(p-toluenesulfonyloxymethyl)uridine
• 英文别名: [(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-3-phenylmethoxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 200435-89-8
• 化学式: C₂₄H₂₆N₂O₉S
• 分子量: 518.544
• InChiKey: YFNGJZQFLAEZHA-GBAAUQCPSA-N

物化性质

• 熔点：
  195-197 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  160
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-O-benzyl-4'-(p-toluenesulfonyloxymethyl)uridine 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 硫酸氢铵 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 氢气 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 145.0h， 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 四氯化钛 、 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以75%的产率得到3'-O-benzyl-4'-(p-toluenesulfonyloxymethyl)uridine
  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

• 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。
• NOVEL BICYCLONUCLEOSIDE AND OLIGONUCLEOTIDE ANALOGUES
  申请人：Imanishi, Takeshi

  公开号：EP1013661A1

  公开（公告）日：2000-06-28

  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 oligonuoleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.

  具有一个或多个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、 或其类似物。使用这种类似物可以得到一种寡核苷酸类似物反义分子，它在体内与酶的水解程度极低，具有较高的有义链结合能力，并且易于合成。
• Novel Bicyclonucleoside and Oligonucleotide Analogue
  申请人：Exiqon A/S

  公开号：EP2295441A2

  公开（公告）日：2011-03-16

  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.

  具有一个或多个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、 或其类似物。使用这种类似物可以得到一种寡核苷酸类似物反义分子，它在体内与酶的水解程度极低，具有较高的有义链结合能力，并且易于合成。