16-(2-chloro-7H-purin-6-yl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 16-(2-chloro-7H-purin-6-yl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecane
• 化学式: C₂₁H₁₈O₂PPol
• 分子量: 415.9
• InChiKey: SNJSTKAXJUYAKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Fmoc-L-丙氨酸 、 Fmoc-L-缬氨酸 、 16-(2-chloro-7H-purin-6-yl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecane 在 哌啶 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2S)-2-[[(2S)-2-acetamidopropanoyl]amino]-3-methyl-N-[(3S)-5-methyl-2-oxo-1-[tris(4-methoxyphenyl)-lambda5-phosphanylidene]hexan-3-yl]butanamide
  参考文献：
  名称：

  Soluble Peptidyl Phosphoranes for Metal-Free, Stereoselective Ligations in Organic and Aqueous Solution

  摘要：

  Protocols for solid-phase syntheses of soluble peptidyl phosphoranes are presented. Various supported phosphoranylldene acetates were prepared on Rink amide or via alkylation of trialkyl- and triarylphosphines with bromoacetyl Wang ester. C-Acylation was conducted racemization-free with activated Fmoc-amino acids, followed by SPPS (solid-phase peptide synthesis). Acidic conditions released decarboxylated peptidyl phosphoranes into solution. The protocol allowed for the electronic variation of peptidyl phosphoranes which were Investigated In ligation reactions with azides In organic and aqueous solvents.

  DOI：

  10.1021/ol202627h
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 2-chloro-6-[N,N-bis(2-hydroxyethyl)amino]purine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以38%的产率得到16-(2-chloro-7H-purin-6-yl)-1,4,7,10,13-pentaoxa-16-azacyclooctadecane
  参考文献：
  名称：

  Synthesis of N-(2-chloro purin-6-yl) aza-18-crown-6 and its interaction with human serum albumin

  摘要：

  描述了 C6 位新型嘌呤核苷连接的氮杂冠醚 N-(2-氯嘌呤-6-基)氮杂-18-冠-6 (NCPAC) 的合成。这种新的核苷类似物可以由一系列 N9 修饰的核苷制备，并且该方法允许对核苷进行新的且简单的修饰。使用分子对接和荧光技术研究了 NCPAC 和人血清白蛋白 (HSA) 之间的相互作用。热力学表明，相互作用是由熵驱动的，主要是疏水力。根据观察到的福斯特型荧光共振能量转移，供体（HSA 中的色氨酸 214）到受体（NCPAC）的距离计算为 3.6 nm。通过同步荧光光谱定性研究了由于相互作用而引起的 HSA 构象变化。进行分子对接研究以获得有关相互作用过程中可能涉及的残基的信息。

  DOI：

  10.1039/c1ob06241g

文献信息

• Synthesis of N-(2-chloro purin-6-yl) aza-18-crown-6 and its interaction with human serum albumin
  作者：Cui Li、Fengling Cui、Runze Mao、Ruina Huo、Guirong Qu

  DOI：10.1039/c1ob06241g

  日期：——

  The synthesis of novel purine nucleosides-linked azacrown ethers in the C6 position, N-(2-chloro purin-6-yl) aza-18-crown-6 (NCPAC), was described. This new nucleoside analogue can be prepared from a series of N9-modified nucleosides and the method allows for new and easy modification of the nucleosides. The interaction between NCPAC and human serum albumin (HSA) was studied using molecular docking and fluorescence techniques. Thermodynamics revealed that the interaction was entropy driven with predominantly hydrophobic forces. From the observed Föster's-type fluorescence resonance energy transfer, the donor (Trp 214 in HSA) to acceptor (NCPAC) distance was calculated to be 3.6 nm. The conformational changes of HSA due to the interaction were investigated qualitatively from synchronous fluorescence spectra. Molecular docking studies were performed to obtain information on the possible residues involved in the interaction process.

  描述了 C6 位新型嘌呤核苷连接的氮杂冠醚 N-(2-氯嘌呤-6-基)氮杂-18-冠-6 (NCPAC) 的合成。这种新的核苷类似物可以由一系列 N9 修饰的核苷制备，并且该方法允许对核苷进行新的且简单的修饰。使用分子对接和荧光技术研究了 NCPAC 和人血清白蛋白 (HSA) 之间的相互作用。热力学表明，相互作用是由熵驱动的，主要是疏水力。根据观察到的福斯特型荧光共振能量转移，供体（HSA 中的色氨酸 214）到受体（NCPAC）的距离计算为 3.6 nm。通过同步荧光光谱定性研究了由于相互作用而引起的 HSA 构象变化。进行分子对接研究以获得有关相互作用过程中可能涉及的残基的信息。
• Soluble Peptidyl Phosphoranes for Metal-Free, Stereoselective Ligations in Organic and Aqueous Solution
  作者：Ahsanullah、Samer I. Al-Gharabli、Jörg Rademann

  DOI：10.1021/ol202627h

  日期：2012.1.6

  Protocols for solid-phase syntheses of soluble peptidyl phosphoranes are presented. Various supported phosphoranylldene acetates were prepared on Rink amide or via alkylation of trialkyl- and triarylphosphines with bromoacetyl Wang ester. C-Acylation was conducted racemization-free with activated Fmoc-amino acids, followed by SPPS (solid-phase peptide synthesis). Acidic conditions released decarboxylated peptidyl phosphoranes into solution. The protocol allowed for the electronic variation of peptidyl phosphoranes which were Investigated In ligation reactions with azides In organic and aqueous solvents.