N-Cbz-L-valinyl propyl amine | 861904-21-4

• 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-Cbz-L-valinyl propyl amine
• 英文别名: (S)-benzyl (3-methyl-1-oxo-1-(propylamino)butan-2-yl)carbamate；ZValNHPr；benzyl N-[(2S)-3-methyl-1-oxo-1-(propylamino)butan-2-yl]carbamate
• CAS: 861904-21-4
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: PROIQIHYUUSYMC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

SDS

MSDS英文版

反应信息

• 作为反应物：
  描述：

  N-Cbz-L-valinyl propyl amine 在 四丁基溴化铵 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 生成 (2S)-3-methyl-2-[[4-[[[(2S)-3-methyl-1-oxo-1-(propylamino)butan-2-yl]amino]methyl]naphthalen-1-yl]methylamino]-N-propylbutanamide
  参考文献：
  名称：

  Novel peptidomimetic macrocycles showing exciplex fluorescence

  摘要：

  The synthesis of five new chiral macrocyclic peptidomimetic naphthalenophanes, together with two open-chain derivatives, is described. The cyclization step is accomplished in good yields without the use of high dilution or template techniques. The new compounds have been photophysically studied by means of steady-state fluorescence spectroscopy. It has been found that the smaller the ring size, the higher the emission quantum yield from the excited charge-transfer state (CTS, exciplex) and the lower the fluorescence from the locally excited state (LES). The occurrence of exciplex fluorescence is noteworthy as the electron-donating groups are secondary amine moieties, which do not normally form emissive exciplexes. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.087
• 作为产物：
  描述：

  L-缬氨酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 N-Cbz-L-valinyl propyl amine
  参考文献：
  名称：

  Synthesis of Chiral Tropopodands Having L-Amino Acid Moieties and Ability of Their Metal Complexes as an Asymmetric Catalyst

  摘要：

  Optical active tropopodands (10 and 11) having neutral L-amino acids and L-histidine moieties were synthesized. Within their metal complexes, Pd complexes of histidine-tropopodands (11b and 11c) bearing bulky amide moieties showed good ability as an asymmetric catalyst in conjugate addition.

  DOI：

  10.3987/com-05-s(t)58

文献信息

• Molecular Hydrogels from Bolaform Amino Acid Derivatives: A Structure-Properties Study Based on the Thermodynamics of Gel Solubilization
  作者：Vicent J. Nebot、José Armengol、Johan Smets、Susana Fernández Prieto、Beatriu Escuder、Juan F. Miravet

  DOI：10.1002/chem.201103193

  日期：2012.3.26

  Insight is provided into the aggregation thermodynamics associated to hydrogel formation by molecular gelators derived from L‐valine and L‐isoleucine. Solubility data from NMR measurements are used to extract thermodynamic parameters for the aggregation in water. It is concluded that at room temperature and up to 55 °C, these systems form self‐assembled fibrillar networks in water with quite low or

  深入了解了由L-缬氨酸和L衍生的分子胶凝剂与水凝胶形成相关的聚集热力学异亮氨酸 来自NMR测量的溶解度数据用于提取在水中聚集的热力学参数。结论是，在室温和高达55°C的温度下，这些系统在水中的焓成分很低或为零，形成了自组装的纤维状网络，而聚集熵却是有利的。考虑到疏水效应在自组装中起主导作用，可以解释这些结果。但是，通过NMR和IR光谱的研究表明，分子间氢键也是这些分子在水中聚集过程中的关键问题。自组装过程中测得的低焓值归因于对分子间氢键形成的有利补偿和疏水作用的不利焓分量的补偿。此外，结果表明，通过使用疏水特性作为设计参数，如果胶凝剂具有足够的极性，则与焓控制的水凝胶形成相反，焓控制的水凝胶形成可以在水中实现。值得注意的是，这两种类型的水凝胶，即焓变熵驱动的水凝胶，对诸如最小胶凝剂浓度（mgc）或流变模量等性质的温度变化表现出截然不同的响应。最后，据报道，加热到70°C以上时，水凝胶中存在
• Mechanistic Insight into the Lability of the Benzyloxycarbonyl (Z) Group in<i>N</i>-Protected Peptides under Mild Basic Conditions
  作者：Marta Tena-Solsona、César A. Angulo-Pachón、Beatriu Escuder、Juan F. Miravet

  DOI：10.1002/ejoc.201400154

  日期：2014.6

  protecting group under mild basic conditions at room temperature is explained by a mechanism based on anchimeric assistance. It is found that the vicinal amide group stabilises the tetrahedral intermediate formed after nucleophilic addition of hydroxide to the carbonyl of the Z group. This effect operates in N-protected tripeptides and tetrapeptides but Z-protected dipeptides are stable under the same conditions

  苄氧羰基 (Z) 保护基团在室温温和碱性条件下出乎意料的不稳定可通过基于嵌合辅助的机制来解释。发现邻酰胺基团稳定了在氢氧化物与 Z 基团的羰基亲核加成后形成的四面体中间体。这种效应在 N 保护的三肽和四肽中起作用，但 Z 保护的二肽在相同条件下是稳定的，因为邻位酰胺 NH 通过与末端羧酸根部分的分子内 H 键合而被阻断。
• 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
• Synthesis, spectroscopic studies and biological evaluation of acridine derivatives: The role of aggregation on the photodynamic efficiency
  作者：Carles Felip-León、Olga Martínez-Arroyo、Santiago Díaz-Oltra、Juan F. Miravet、Nadezda Apostolova、Francisco Galindo

  DOI：10.1016/j.bmcl.2018.02.005

  日期：2018.3

  a strong tendency to aggregate in water. Biological assays were conducted with two cell types: hepatoma cells (Hep3B) and human umbilical vein endothelial cells (HUVEC). Photodynamic therapy (PDT) studies carried out with Hep3B cells showed that non-aggregating compound 2 showed photoxicity, ascribed to the production of singlet oxygen, being aggregating compound 1 photochemically inactive. On the other

  合成并充分表征了衍生自9-ami啶基发色团的两种新的光敏化合物（1和2）。比较了它们在辐照下产生单线态氧的能力。因为仅合成的化合物显示出非常不同的自聚集性能1存在于水中来聚合的强烈倾向。用两种细胞类型进行了生物学测定：肝癌细胞（Hep3B）和人脐静脉内皮细胞（HUVEC）。用Hep3B细胞进行的光动力疗法（PDT）研究表明，非聚集化合物2显示光毒性，这归因于产生单线态氧，是聚集化合物1。光化学惰性。另一方面，特征在于纳米级聚集体的1的悬浮液在黑暗中对该细胞系具有显着的抗增殖活性。
• Diamine acylation with amino acid derivatives: an example of proximity effect in organic reactivity induced by supramolecular aggregation
  作者：Carles Felip-León、María D. Segarra-Maset、Beatriu Escuder、Juan F. Miravet

  DOI：10.1016/j.tetlet.2015.01.094

  日期：2015.2

  Unexpected high yields of diamide 3 are obtained in the reaction of 1,3-propanediamine with an activated ester of L-valine (1) under adverse proportions of the reactants, namely in the presence of an excess of 1,3-propanediamine. It is observed using different conditions that the yield of difunctionalized compound is considerably higher than that expected from a statistical distribution of products. Proximity effects associated to supramolecular interactions explain the described reactivity. (C) 2015 Elsevier Ltd. All rights reserved.