N,N'-bis(N-Cbz-L-valinyl)-1,8-diaminooctane | 553668-51-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-bis(N-Cbz-L-valinyl)-1,8-diaminooctane
• 英文别名: dibenzyl ((2S,2'R)-(octane-1,8-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl))dicarbamate；dibenzyl ((2S,2'S)-(octane-1,8-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl))dicarbamate；benzyl N-[(2S)-3-methyl-1-[8-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]octylamino]-1-oxobutan-2-yl]carbamate
• CAS: 553668-51-2
• 化学式: C₃₄H₅₀N₄O₆
• 分子量: 610.794
• InChiKey: PYSBBUDSIXMWGJ-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  44
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(N-Cbz-L-valinyl)-1,8-diaminooctane 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以99%的产率得到N,N'-bis(L-valinyl)-1,8-diaminooctane
  参考文献：
  名称：

  Insight into the esterase like activity demonstrated by an imidazole appended self-assembling hydrogelator

  摘要：

  首次报道了一种简单的咪唑修饰的水凝胶体系对未活化苯丙氨酸甲酯的水解作用。

  DOI：

  10.1039/c5cc04281j
• 作为产物：
  描述：

  CBZ-L-缬氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 9.0h， 生成 N,N'-bis(N-Cbz-L-valinyl)-1,8-diaminooctane
  参考文献：
  名称：

  Insight into the esterase like activity demonstrated by an imidazole appended self-assembling hydrogelator

  摘要：

  首次报道了一种简单的咪唑修饰的水凝胶体系对未活化苯丙氨酸甲酯的水解作用。

  DOI：

  10.1039/c5cc04281j

文献信息

• Efficient Macrocyclization of U-Turn Preorganized Peptidomimetics:  The Role of Intramolecular H-Bond and Solvophobic Effects
  作者：Jorge Becerril、Michael Bolte、M. Isabel Burguete、Francisco Galindo、Enrique García-España、Santiago V. Luis、Juan F. Miravet

  DOI：10.1021/ja0284759

  日期：2003.6.1

  acetonitrile to very efficiently yield macrocyclic structures. The cyclization reaction does not require high dilution techniques and seems to be insensitive to the size of the formed macrocycle. The analysis of data obtained by (1)H NMR, single-crystal X-ray diffraction, fluorescence measurements, and molecular mechanics indicate that folded conformations can preorganize the system for an efficient cyclization

  源自氨基酸的简单拟肽分子在乙腈中与间位和对位双（溴甲基）苯反应，非常有效地产生大环结构。环化反应不需要高稀释技术，并且似乎对形成的大环的大小不敏感。通过 (1)H NMR、单晶 X 射线衍射、荧光测量和分子力学获得的数据分析表明，折叠构象可以预先组织系统以实现有效的环化。分析了在折叠构象存在下分子内氢键和疏溶剂效应所起的作用。
• New chiral tetraaza ligands for the efficient enantioselective addition of dialkylzinc to aromatic aldehydes
  作者：M. Isabel Burguete、Jorge Escorihuela、Santiago V. Luis、Agustí Lledós、Gregori Ujaque

  DOI：10.1016/j.tet.2008.07.099

  日期：2008.10

  enantioselective addition of dialkylzinc to aldehydes. These bis(amino amide) ligands show high enantioselectivity in the addition of organozincs to aromatic aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Ligand 4b (N,N′-bis(N-l-valinyl)-1,3-diaminopropane, with an aliphatic spacer with 3C atoms) catalyzed the addition of Et2Zn

  研究了一系列手性四氮杂配体，用于将二烷基锌对映体选择性加成到醛中。这些双（氨基酰胺）配体在将有机锌添加到芳族醛中时显示出高对映选择性。配体上的不同结构元素似乎在确定观察到的对映选择性中起重要作用。配体4b（N，N'-双（N -1-戊基）-1,3-二氨基丙烷，带有带有3C原子的脂族间隔基）催化Et 2的添加锌转化为苯甲醛，1-萘醛，4-甲氧基苯甲醛和4-氯苯甲醛，得到相应的醇产物，其转化率和选择性极好，对映选择性分别为99％，97％，98％和82％。DFT计算提供了对映过程的机理的理解。
• Fabrication of helical hybrid silica bundles
  作者：Yonggang Yang、Miho Nakazawa、Masahiro Suzuki、Hirofusa Shirai、Kenji Hanabusa

  DOI：10.1039/b700615b

  日期：——

  A series of C2-symmetric bridged silsesquioxanes derived from L- and D-valine have been designed and synthesized. They were capable of forming physical gels in organic solvents such as ethanol, THF, and 1,4-dioxane. These silsesquioxanes formed helical bundles in 1,4-dioxane. With respect to the helical sense, a clear odd–even effect was found in the carbon number of the central alkylene segment. The silsesquioxanes with odd number alkylene segments derived from L-valine tended to self-assemble into right-handed helical bundles. On the contrary, those with even number alkylene segments tended to form left-handed helical bundles. Moreover, enantiomers derived from D-valine showed the opposite helical sense. The p : d ratio played an important role in the determination of helical sense. After sol–gel polycondensation under catalysts such as HCl, NaOH, and TBAF, helical hybrid silica bundles were identified in FESEM images. The helical sense of the bundles was sensitive to the catalysts and reaction conditions. Hybrid silica sponges showing both superoleophilic and superhydrophobic properties were obtained under a HCl diffusion procedure.

  一系列源自L-和D-缬氨酸的C2对称桥接硅烷氧烷已被设计和合成。这些化合物能够在乙醇、四氢呋喃和1,4-二氧烷等有机溶剂中形成物理凝胶。这些硅烷氧烷在1,4-二氧烷中形成螺旋束。在螺旋方向上，发现中央烷基段的碳原子数存在明显的奇偶效应。源自L-缬氨酸的奇数烷基段硅烷氧烷倾向于自组装成右手螺旋束。相反，偶数烷基段的则倾向于形成左手螺旋束。此外，源自D-缬氨酸的对映体表现出相反的螺旋方向。p : d 比例在确定螺旋方向上发挥了重要作用。在HCl、NaOH和TBAF等催化剂的作用下，经过溶胶-凝胶聚缩合后，通过FESEM图像可以识别出螺旋混合硅氧化物束。这些束的螺旋方向对催化剂和反应条件敏感。在HCl扩散过程中获得了显示超级亲油和超级疏水特性的混合硅海绵。
• Synthesis and Evaluation of Pseudopeptidic Fluorescence pH Probes for Acidic Cellular Organelles: In Vivo Monitoring of Bacterial Phagocytosis by Multiparametric Flow Cytometry
  作者：M. Isabel Burguete、Francisco Galindo、M. Angeles Izquierdo、José-Enrique O'Connor、Guadalupe Herrera、Santiago V. Luis、Laura Vigara

  DOI：10.1002/ejoc.201000854

  日期：2010.11

  applications of this family of probes, macrocyclic pseudopeptide 2 was used to monitor the phagocytosis of a culture of GFP-labelled bacteria by human monocytic cells U937 using flow cytometry as the analytical tool. It was found that the occurrence of bacterial killing was concomitant with the production of reactive oxygen species and a drop in pH, the latter monitored indirectly by macrocyclic sensor

  合成了一类新的荧光蒽 pH 探针，并对其进行了化学表征，并通过稳态和时间分辨荧光光谱研究了它们的光物理特性。已经在溶液中研究了这些化合物监测 pH 值的能力，并且发现分子 1-12 可以充当 4.6 和 6.5 范围内 pH 值的荧光传感器。该范围对应于描述了有限数量探针的细胞中酸性细胞器的 pH 值（pH 4.5-6.0）。每个传感器的酸碱行为略有不同，具体取决于分子中存在的胺附近的取代基的性质。Thus, the pK a of this family of compounds can be finely tuned by the appropriate selection of the synthetic building blocks at the design stage. 为了测试该探针家族的潜在诊断应用，使用流式细胞术作为分析工具，使用大环假肽 2 来监测人类单核细胞 U937
• Synthetic Macrocyclic Peptidomimetics as Tunable pH Probes for the Fluorescence Imaging of Acidic Organelles in Live Cells
  作者：Francisco Galindo、M. Isabel Burguete、Laura Vigara、Santiago V. Luis、Nurul Kabir、Jelena Gavrilovic、David A. Russell

  DOI：10.1002/anie.200501920

  日期：2005.10.14