(2R,3S,4R,5R)-2-Hydroxymethyl-5-(6-tetradecylamino-purin-9-yl)-tetrahydro-furan-3,4-diol | 126705-13-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2R,3S,4R,5R)-2-Hydroxymethyl-5-(6-tetradecylamino-purin-9-yl)-tetrahydro-furan-3,4-diol
• CAS: 126705-13-3
• 化学式: C₂₄H₄₁N₅O₄
• 分子量: 463.621
• InChiKey: MCRTYJWERWXDQY-UMCMBGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  33.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  125.55
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-2-Hydroxymethyl-5-(6-tetradecylamino-purin-9-yl)-tetrahydro-furan-3,4-diol 在 三氯氧磷 作用下， 生成
  参考文献：
  名称：

  Kotrokois, C.; Granet, R.; Piekarski, S., Journal de Chimie Physique et de Physico-Chimie Biologique, 1988, vol. 85, # 3, p. 399 - 404

  摘要：

  DOI：
• 作为产物：
  描述：

  十四胺 在 2.) hydrolysis 作用下， 生成 (2R,3S,4R,5R)-2-Hydroxymethyl-5-(6-tetradecylamino-purin-9-yl)-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Kotrokois, C.; Granet, R.; Piekarski, S., Journal de Chimie Physique et de Physico-Chimie Biologique, 1988, vol. 85, # 3, p. 399 - 404

  摘要：

  DOI：

文献信息

• Carbodiimide‐Driven Dimerization and Self‐Assembly of Artificial, Ribose‐Based Amphiphiles
  作者：Jing Sun、Julian Vogel、Lisa Chen、A. Lennart Schleper、Tim Bergner、Alexander J. C. Kuehne、Max Delius

  DOI：10.1002/chem.202104116

  日期：2022.3

  AbstractThe aqueous self‐assembly of amphiphiles into aggregates such as micelles and vesicles has been widely investigated over the past decades with applications ranging from materials science to drug delivery. The combination of characteristic properties of nucleic acids and amphiphiles is of substantial interest to mimic biological self‐organization and compartmentalization. Herein, we present ribose‐ and ribonucleotide‐based amphiphiles and investigate their self‐assembly as well as their fundamental reactivity. We found that various types of aggregates are formed, ranging in size from nanometers to micrometers and all amphiphiles exhibit aggregation‐induced emission (AIE) in solution as well as in the solid state. We also observed that the addition of 1‐ethyl‐3‐(3‐dimethylaminopropyl)carbodiimide (EDC) leads to rapid and selective dimerization of the amphiphiles into pyrophosphates, which decreases the critical aggregation concentration (CAC) by a factor of 25 when compared to the monomers. Since the propensity for amphiphile dimerization is correlated with their tendency to self‐assemble, our results may be relevant for the formation of rudimentary compartments under prebiotic conditions.