1,4,7-tris[(cholesteryloxycarbonyl)methyl]-1,4,7-triazacyclononane | 1246210-95-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1,4,7-tris[(cholesteryloxycarbonyl)methyl]-1,4,7-triazacyclononane
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-[4,7-bis[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2-oxoethyl]-1,4,7-triazonan-1-yl]acetate
• CAS: 1246210-95-6
• 化学式: C₉₃H₁₅₃N₃O₆
• 分子量: 1409.25
• InChiKey: HTMOAGOXNBDEFL-OAUWGUKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.9
• 重原子数：
  102
• 可旋转键数：
  27
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  88.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  氯乙酸胆固醇 、 1,4,7-triazacyclononane trihydrochloride 在 potassium carbonate 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 8.5h， 以91%的产率得到1,4,7-tris[(cholesteryloxycarbonyl)methyl]-1,4,7-triazacyclononane
  参考文献：
  名称：

  Mechanical Tuning of Molecular Recognition To Discriminate the Single-Methyl-Group Difference between Thymine and Uracil

  摘要：

  Construction of enzyme-like artificial cavities is a complex and challenging subject. Rather than synthesizing complicated host molecules, we have proposed mechanical adaptation of relatively simple hosts within dynamic media to determine the optimum conformation for molecular recognition. Here we have applied this concept to one of the most challenging biomolecular recognition problems, i.e., that of discriminating thymine from uracil. We synthesized the novel cholesterol-armed triazacyclononane as a host molecule and subjected it to structural tuning by compression of its Langmuir monolayers in the absence and in the presence of Li+ cations in the subphase. Experimental results confirm that the monolayer of triazacyclononane host selectively recognizes uracil over adenine (ca. 7 times based on the binding constant) and thymine (ca. 64 times) under optimized conditions ([LiCl] = 10 mM at surface pressure of 35 mN m(-1)). The concept of mechanical tuning of a host structure for optimization of molecular recognition offers a novel methodology in host guest chemistry as an alternative to the more traditional molecular design strategies.

  DOI：

  10.1021/ja106653a

文献信息

• Mechanical Tuning of Molecular Recognition To Discriminate the Single-Methyl-Group Difference between Thymine and Uracil
  作者：Taizo Mori、Ken Okamoto、Hiroshi Endo、Jonathan P. Hill、Satoshi Shinoda、Miki Matsukura、Hiroshi Tsukube、Yasumasa Suzuki、Yasumasa Kanekiyo、Katsuhiko Ariga

  DOI：10.1021/ja106653a

  日期：2010.9.22

  Construction of enzyme-like artificial cavities is a complex and challenging subject. Rather than synthesizing complicated host molecules, we have proposed mechanical adaptation of relatively simple hosts within dynamic media to determine the optimum conformation for molecular recognition. Here we have applied this concept to one of the most challenging biomolecular recognition problems, i.e., that of discriminating thymine from uracil. We synthesized the novel cholesterol-armed triazacyclononane as a host molecule and subjected it to structural tuning by compression of its Langmuir monolayers in the absence and in the presence of Li+ cations in the subphase. Experimental results confirm that the monolayer of triazacyclononane host selectively recognizes uracil over adenine (ca. 7 times based on the binding constant) and thymine (ca. 64 times) under optimized conditions ([LiCl] = 10 mM at surface pressure of 35 mN m(-1)). The concept of mechanical tuning of a host structure for optimization of molecular recognition offers a novel methodology in host guest chemistry as an alternative to the more traditional molecular design strategies.