2'-O-(2-hydroxyethyl)-3',5'-O-tetraisopropyl-di-siloxyl-N³-benzyloxymethyl-5-methyl uridine | 200423-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-(2-hydroxyethyl)-3',5'-O-tetraisopropyl-di-siloxyl-N³-benzyloxymethyl-5-methyl uridine
• 英文别名: 1-[(6aR,8R,9R,9aR)-9-(2-hydroxyethoxy)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-5-methyl-3-(phenylmethoxymethyl)pyrimidine-2,4-dione
• CAS: 200423-86-5
• 化学式: C₃₂H₅₂N₂O₉Si₂
• 分子量: 664.944
• InChiKey: NCJBNEJAKDUMSG-BUVRPPHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-O-(2-hydroxyethyl)-3',5'-O-tetraisopropyl-di-siloxyl-N³-benzyloxymethyl-5-methyl uridine 在 palladium on activated charcoal 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium azide 、 四丁基氟化铵 、 氢气 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.25h， 生成 [2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]thymine
  参考文献：
  名称：

  Dual Recognition of Double-Stranded DNA by 2′-Aminoethoxy-Modified Oligonucleotides

  摘要：

  Simultaneous interaction of the 2'-aminoethoxy-modified oligonucleotides with the phosphodiester backbone (shown on the right, A) and with the bases through Hoogsteen base contacts (B) is seen at each base-pair step of the duplex DNA target. The electrostatic interaction between the protonated amino group and the negatively charged phosphate group provides for a dramatic increase in the binding affinity and the association rate constant.

  DOI：

  10.1002/(sici)1521-3773(19980518)37:9<1288::aid-anie1288>3.0.co;2-u
• 作为产物：
  描述：

  [(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester 在 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 以84%的产率得到2'-O-(2-hydroxyethyl)-3',5'-O-tetraisopropyl-di-siloxyl-N³-benzyloxymethyl-5-methyl uridine
  参考文献：
  名称：

  Dual Recognition of Double-Stranded DNA by 2′-Aminoethoxy-Modified Oligonucleotides

  摘要：

  Simultaneous interaction of the 2'-aminoethoxy-modified oligonucleotides with the phosphodiester backbone (shown on the right, A) and with the bases through Hoogsteen base contacts (B) is seen at each base-pair step of the duplex DNA target. The electrostatic interaction between the protonated amino group and the negatively charged phosphate group provides for a dramatic increase in the binding affinity and the association rate constant.

  DOI：

  10.1002/(sici)1521-3773(19980518)37:9<1288::aid-anie1288>3.0.co;2-u

文献信息

• Enhancement and Inhibition by 2′-O-Hydroxyethyl Residues of Gene Targeting Mediated by Triple Helix Forming Oligonucleotides
  作者：Mrinalkanti Kundu、Fumi Nagatsugi、Alokes Majumdar、Paul S. Miller、Michael M. Seidman

  DOI：10.1081/ncn-120025240

  日期：2003.10.1

  Reagents that recognize and bind specific genomic sequences in living mammalian cells would have great potential for genetic manipulation, including gene knockout, strain construction, and gene therapy. Triple helix forming oligonucleotides (TFOs) bind specific sequences via the major groove, but pyrimidine motif TFOs are limited by their poor activity under physiological conditions. Base and sugar analogues that overcome many of these limitations have been described. In particular, 2'-O-modifications influence sugar pucker and third strand conformation, and have been important to the development of bioactive TFOs. Here we have analyzed the impact of 2'-O-hydroxyethyl (2'-HE) substitutions, in combination with other 2' modifications. We prepared modified TFOs conjugated to psoralen and measured targeting activity in a gene knockout assay in cultured hamster cells. We find that 2'-HE residues enhance the bioactivity of TFOs containing 2'-O-methyl (2'-OMe) modifications, but reduce the bioactivity of TFOs containing, in addition, 2'-O-aminoethyl (2'-AE) residues.
• Dual Recognition of Double-Stranded DNA by 2′-Aminoethoxy-Modified Oligonucleotides
  作者：Bernard Cuenoud、Florence Casset、Dieter Hüsken、François Natt、Romain M. Wolf、Karl-Heinz Altmann、Pierre Martin、Heinz E. Moser

  DOI：10.1002/(sici)1521-3773(19980518)37:9<1288::aid-anie1288>3.0.co;2-u

  日期：1998.5.18

  Simultaneous interaction of the 2'-aminoethoxy-modified oligonucleotides with the phosphodiester backbone (shown on the right, A) and with the bases through Hoogsteen base contacts (B) is seen at each base-pair step of the duplex DNA target. The electrostatic interaction between the protonated amino group and the negatively charged phosphate group provides for a dramatic increase in the binding affinity and the association rate constant.