3'-O-acetyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside | 185672-53-1

• 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: 3'-O-acetyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside
• 英文别名: 2'-deoxy-3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-4-[1,2,4]triazol-1-yl-5-methylcytidine
• CAS: 185672-53-1
• 化学式: C₃₅H₃₅N₅O₇
• 分子量: 637.692
• InChiKey: ARNWLBKDTHGEIU-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  128.82
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside 在 甲醇 、 TEA 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 1-[6-(1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-ylamino)-hexylamino]-anthraquinone
  参考文献：
  名称：

  α–β Chimeric oligo-DNA bearing intercalator-conjugated nucleobase inside the linker sequence remarkably improves thermal stability of an alternate-stranded triple helix

  摘要：

  Novel alpha-beta chimeric oligodeoxynucleotides bearing an intercalator-conjugated nucleobase located at the internal 4-nt linker region were synthesized, and their triplex-stabilizing property was examined. The triple helical DNA formed between the modified chimera DNA and double-stranded DNA exhibited remarkable thermal stability; however, the position of the intercalator-conjugated nucleobase had little influence on the stability. Among the examined, modified chimera DNA bearing the two intercalator-conjugated nucleobases at adjacent positions exhibited the highest stability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.055
• 作为产物：
  描述：

  保护胸苷 在 吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 29.0h， 生成 3'-O-acetyl-5'-O-dimethoxytrityl-1-[5-methyl-4-triazolylpyrimidin-2(1H)-onyl]-β-D-2'-deoxyriboside
  参考文献：
  名称：

  Insertion of 5-methyl-N4-(1-pyrenylmethyl)cytidine into DNA. Duplex, three-way junction and triplex stabilities

  摘要：

  5'-O-(4,4'-Dimethoxytrityl)-5-methyl-N-4-(1-pyrenylmethyl)cytidine (5) was prepared by reaction of 1-pyrenylmethylamine with an appropriate protected 4-(1,2,4-triazolyl)thymidine derivative which was synthesized from 5-O-DMT protected thymidine by acetylation with acetic anhydride and subsequent reaction with triethylamine, 1,2,4-triazole and POCl3. Stabilities are reported for DNA duplexes, three-way junctions and triplexes when 5 is inserted. Most interestingly, the three-way junctions are stabilized when 5 is used for insertion into the junction region. This break-through for recognizing the foot of a stem could have far-reaching importance because new targets for antisense oligos is now rendered possible on intact secondary structures. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4020(96)00933-7

文献信息

• Synthesis of modified oligonucleotides containing 4-guanidino-2-pyrimidinone nucleobases
  作者：Jordi Robles、Anna Grandas、Enrique Pedroso

  DOI：10.1016/s0040-4020(00)00991-1

  日期：2001.1

  Oligionucleotides incorporating 4-guanidino-2-pyrimidinone nucleobases have been prepared. These nucleobase analogues were designed to mimic the double hydrogen bond donor pattern of protonated cytosines in parallel triple helices. Guanidine-, N-methyl-, N,N-dimethyl-, and N,N'-dimethylguanidine-containing nucleoside H-phosphonates were used for the synthesis of oligonucleotide analogues with minor modifications in standard solid-phase procedures. (C) 2000 Elsevier Science Ltd. All rights reserved.