1-[(2R,4S,5R)-4-[4-[[(2R,3S,5R)-3-[4-[[(2R,3S,5R)-3-[4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione | 1350443-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2R,4S,5R)-4-[4-[[(2R,3S,5R)-3-[4-[[(2R,3S,5R)-3-[4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1350443-41-2
• 化学式: C₄₈H₅₃N₁₇O₁₃
• 分子量: 1076.05
• InChiKey: ROZPYXUYJTZWPY-YOJLFLLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  78
• 可旋转键数：
  14
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  347
• 氢给体数：
  5
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-azido-5-[[1-[(2R,3S,5R)-2-[[1-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]triazol-4-yl]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]triazol-4-yl]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 、 1-[(2R,4S,5R)-4-[4-[[(2R,3S,5R)-3-[4-[[(2R,3S,5R)-3-[4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 二甲基硫 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 1.0h， 以33.2 mg的产率得到
  参考文献：
  名称：

  Convergent synthesis of oligomers of triazole-linked DNA analogue (TLDNA) in solution phase

  摘要：

  A convergent route for the solution-phase synthesis of oligomeric triazole-linked analogues of DNA ((TL)DNA) has been developed. A one-pot procedure for desilylation of masked acetylene and the ensuing copper-catalyzed Huisgen coupling reaction between oligomers allowed the solution-phase synthesis of 7-mer and 8-mer (TL)DNA in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.101
• 作为产物：
  描述：

  1-[(2R,4S,5R)-4-[4-[[(2R,3R,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 吡啶 、 sodium azide 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.33h， 生成 1-[(2R,4S,5R)-4-[4-[[(2R,3S,5R)-3-[4-[[(2R,3S,5R)-3-[4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  三唑连接的DNA作为第一链cDNA合成中的引物替代品

  摘要：

  磷酸消除的非天然寡核苷酸可作为mRNA逆转录反应中的引物替代物。尽管在替代物中存在非天然三唑键，但逆转录酶通过转录mRNA的互补序列有效地延长了引物3'下游的cDNA序列。与参考天然寡核苷酸的结构活性比较表明，含有三唑键的替代物具有更好的引发活性。非天然连接还可以保护转录的cDNA免于与5'-核酸外切酶的消化反应，并使我们能够去除未知来源的噪音转录本。

  DOI：

  10.1002/asia.201100712

文献信息

• Post-Modification of Triazole-Linked Analogues of DNA for Positively Charged Variants
  作者：Hiroyuki Isobe、Tomoko Fujino、Yusuke Miyauchi、Nobuhide Tsunaka、Koudai Okada

  DOI：10.3987/com-13-12697

  日期：——

  We report a concise post-modification method to convert an electroneutral triazole-linked DNA ((TL)DNA) to a positively charged triazolium-linked analogue, (TL)DNA+. A one-step methylation of oligothymine (TL)DNA successfully afforded (TL)DNA+ with a dramatic improvement in the solubility. The pentameric oligothymine (TL)DNA+ formed a stable triple helix with natural oligoadenine DNA as well as a mercury-mediated self-duplex.
• Convergent synthesis of oligomers of triazole-linked DNA analogue (TLDNA) in solution phase
  作者：Tomoko Fujino、Naomi Yamazaki、Hiroyuki Isobe

  DOI：10.1016/j.tetlet.2009.04.101

  日期：2009.7

  A convergent route for the solution-phase synthesis of oligomeric triazole-linked analogues of DNA ((TL)DNA) has been developed. A one-pot procedure for desilylation of masked acetylene and the ensuing copper-catalyzed Huisgen coupling reaction between oligomers allowed the solution-phase synthesis of 7-mer and 8-mer (TL)DNA in good yield. (C) 2009 Elsevier Ltd. All rights reserved.
• Triazole-Linked DNA as a Primer Surrogate in the Synthesis of First-Strand cDNA
  作者：Tomoko Fujino、Ken-ichi Yasumoto、Naomi Yamazaki、Ai Hasome、Kazuhiro Sogawa、Hiroyuki Isobe

  DOI：10.1002/asia.201100712

  日期：2011.11.4

  A phosphate‐eliminated nonnatural oligonucleotide serves as a primer surrogate in reverse transcription reaction of mRNA. Despite of the nonnatural triazole linkages in the surrogate, the reverse transcriptase effectively elongated cDNA sequences on the 3′‐downstream of the primer by transcription of the complementary sequence of mRNA. A structure–activity comparison with the reference natural oligonucleotides

  磷酸消除的非天然寡核苷酸可作为mRNA逆转录反应中的引物替代物。尽管在替代物中存在非天然三唑键，但逆转录酶通过转录mRNA的互补序列有效地延长了引物3'下游的cDNA序列。与参考天然寡核苷酸的结构活性比较表明，含有三唑键的替代物具有更好的引发活性。非天然连接还可以保护转录的cDNA免于与5'-核酸外切酶的消化反应，并使我们能够去除未知来源的噪音转录本。