2-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-1-isoquinolone | 600707-57-1

• 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-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-1-isoquinolone
• 英文别名: 2-[(1R,3R,4R,7S)-1-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-3-yl]isoquinolin-1-one
• CAS: 600707-57-1
• 化学式: C₃₆H₃₃NO₇
• 分子量: 591.661
• InChiKey: JRJVSYIHUOIVQJ-WJKMXKTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 2-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-1-isoquinolone 在 二异丙基铵盐四氮唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 以97%的产率得到2-[3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-1-isoquinolone
  参考文献：
  名称：

  Selective recognition of CG interruption by 2′,4′-BNA having 1-isoquinolone as a nucleobase in a pyrimidine motif triplex formation

  摘要：

  To develop a novel nucleoside analogue for the effective recognition of CG interruption in a homopurine-homopyrimidine tract of double-stranded DNA (dsDNA), we succeeded in the synthesis of a triplex-forming oligonucleotide (TFO) containing a novel 2',4'-BNA (Q(B)) bearing 1-isoquinolone as a nucleobase, and the triplex-forming ability and sequence-selectivity of the TFO (TFO-Q(B)) were examined. On melting temperature (T-m) measurements, it was found that the TFO-Q(B) formed a stable triplex DNA in a highly sequence-selective manner under near physiological conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00728-2
• 作为产物：
  描述：

  1-羟基异喹啉 在 palladium dihydroxide 吡啶 、 N,O-双三甲硅基乙酰胺 、 potassium carbonate 、 环己烯 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 2-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-1-isoquinolone
  参考文献：
  名称：

  Selective recognition of CG interruption by 2′,4′-BNA having 1-isoquinolone as a nucleobase in a pyrimidine motif triplex formation

  摘要：

  To develop a novel nucleoside analogue for the effective recognition of CG interruption in a homopurine-homopyrimidine tract of double-stranded DNA (dsDNA), we succeeded in the synthesis of a triplex-forming oligonucleotide (TFO) containing a novel 2',4'-BNA (Q(B)) bearing 1-isoquinolone as a nucleobase, and the triplex-forming ability and sequence-selectivity of the TFO (TFO-Q(B)) were examined. On melting temperature (T-m) measurements, it was found that the TFO-Q(B) formed a stable triplex DNA in a highly sequence-selective manner under near physiological conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00728-2

文献信息

• Selective recognition of CG interruption by 2′,4′-BNA having 1-isoquinolone as a nucleobase in a pyrimidine motif triplex formation
  作者：Yoshiyuki Hari、Satoshi Obika、Mitsuaki Sekiguchi、Takeshi Imanishi

  DOI：10.1016/s0040-4020(03)00728-2

  日期：2003.6

  To develop a novel nucleoside analogue for the effective recognition of CG interruption in a homopurine-homopyrimidine tract of double-stranded DNA (dsDNA), we succeeded in the synthesis of a triplex-forming oligonucleotide (TFO) containing a novel 2',4'-BNA (Q(B)) bearing 1-isoquinolone as a nucleobase, and the triplex-forming ability and sequence-selectivity of the TFO (TFO-Q(B)) were examined. On melting temperature (T-m) measurements, it was found that the TFO-Q(B) formed a stable triplex DNA in a highly sequence-selective manner under near physiological conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.