(2R,3S,5R)-2-(4,4'-dimethoxytrityloxymethyl)-3-hydroxy-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran | 1039665-17-2

• 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: (2R,3S,5R)-2-(4,4'-dimethoxytrityloxymethyl)-3-hydroxy-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran
• 英文别名: 5-[2-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]ethynyl]-1-methylpyrimidine-2,4-dione
• CAS: 1039665-17-2
• 化学式: C₃₃H₃₂N₂O₇
• 分子量: 568.626
• InChiKey: IWJXVUKROJOKTP-OIFRRMEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-2-(4,4'-dimethoxytrityloxymethyl)-3-hydroxy-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran 在 吡啶 、 4-二甲氨基吡啶 、 三氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成
  参考文献：
  名称：

  Synthesis of Alkynyl C-Nucleotide Triphosphates Toward Enzymatic Elongation of Artificial DNA

  摘要：

  Four types of alkynyl C-nucleotide triphosphates were synthesized, in which heterocyclic compounds as a non-natural nucleobase were tethered to deoxyribose through acetylene bonds. The non-natural nucleobases are D*, T*, G*, and C*, corresponding to natural A, T, G, and C, respectively, from a hydrogen-bonding pattern of view. All the non-natural triphosphates were found to be a good substrate for terminal deoxynucleotidyl transferase (TdT), a natural nucleic acid-relevant enzyme.

  DOI：

  10.3987/com-18-s(t)48

文献信息

• Furanose ring conformations in a 1′-alkynyl C-nucleoside and the dinucleotide
  作者：Junya Chiba、Wataru Shirato、Yusuke Yamade、Byung-Soon Kim、Shinya Matsumoto、Masahiko Inouye

  DOI：10.1016/j.tet.2012.08.057

  日期：2012.11

  A large-scale synthesis was carried out for alkynyl C-nucleotide oligomers in order to clarify the structural details of the artificial DNA. A liquid-phase synthesis by means of phosphoramidite methodology enabled us to handle similar to 0.1 g of the DNA oligomers possessing a pseudouracil derivative (T*) as a non-natural nucleobase. H-1 NMR measurements in aqueous media were carried out for the oligomers, succeeded in the accurate assignments of the protons accompanying with determination of the coupling constants (J values). These J values revealed that average conformation of the alkynylribose rings in the DNA was substantially biased toward the S-type conformers (T-2(1)/E-1/T-0(1)). X-ray crystal analysis of the non-natural nucleoside also supported the S-type conformation (E-2/T-2(1)) as seen in natural B-DNA. (C) 2012 Elsevier Ltd. All rights reserved.