5-[2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]ethynyl]-1-methylpyrimidine-2,4-dione | 1039665-23-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5-[2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]ethynyl]-1-methylpyrimidine-2,4-dione
• CAS: 1039665-23-0
• 化学式: C₁₂H₁₄N₂O₅
• 分子量: 266.254
• InChiKey: ACHRPBCWBSBOOU-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,3S,5R)-2-(4,4'-dimethyltrityloxymethyl)-3-hydroxy-5-(1-methylpyrimidin-2,4-dion-5-ylethynyl)tetrahydrofuran 在 三氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以66%的产率得到5-[2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]ethynyl]-1-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Artificial DNA Made Exclusively of Nonnatural C-Nucleosides with Four Types of Nonnatural Bases

  摘要：

  We describe a new class of DNA-like oligomers made exclusively of nonnatural, stable C-nucleosides. The nucleosides comprise four types of nonnatural bases attached to a deoxyribose through an acetylene bond with the beta-configuration. The artificial DNA forms right-handed duplexes and triplexes with the complementary artificial DNA. The hybridization occurs spontaneously and sequence-selectively, and the resulting duplexes have thermal stabilities very close to those of natural duplexes. The artificial DNA might be applied to a future extracellular genetic system with information storage and amplifiable abilities.

  DOI：

  10.1021/ja801058h

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.