PheA6 | 73787-46-9

• 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: PheA6
• 英文别名: 1,6-Di(l-phenylalaninamido)hexane；(2S)-2-amino-N-[6-[[(2S)-2-amino-3-phenylpropanoyl]amino]hexyl]-3-phenylpropanamide
• CAS: 73787-46-9
• 化学式: C₂₄H₃₄N₄O₂
• 分子量: 410.56
• InChiKey: MYCVLSPAYPTYJH-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  PheA6 在 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 N¹,N⁶-bis(D-Phe-L-Phe)hexanediamine
  参考文献：
  名称：

  Diastereomeric Selective Effects for Growth Inhibition of Synthesized Mini Parallel Double-Stranded Peptides on Escherichia coli and Staphylococcus aureus

  摘要：

  描述了一系列含有手性-x-Phe-y-Phe-肽残基的迷你双链肽的合成，以及这些化合物对大肠杆菌NIHJ JC-2和金黄色葡萄球菌FDA 209P生长的非对映选择性效应。以双(y-Phe-x-Phe)-N,N-乙烷-1,2-二胺、双(y-Phe-x-Phe)-N,N-丁烷-1,4-二胺、双(y-Phe-x-Phe)-N,N-己烷-1,6-二胺和双(y-Phe-x-Phe)-N,N-十二烷-1,12-二胺等为例，使用了四种构型(L-,L-)、(D-,L-)、(L-,D-)和(D-,D-)（其中符号x-和y-表示具有L-和D-形式的光学异构体），以研究手性与抗菌活性之间的关系。活性水平按以下顺序增加：(L-,L-)<(D-,D-)<(L-,D-)<(D-,L-)。数据显示，(D-,L-)手性比(L-,L-)手性更有效。这些结果表明，双链肽中的-y-Phe-x-Phe Phe-序列具有抗菌活性，而-y-Phe-x-Phe的手性影响抗菌活性。我们的结果表明，通过膜渗透摄取双(y-Phe-x-Phe)2-间隔物是表达抗菌活性的第一步。本研究为一系列迷你双链肽的手性-抗菌活性关系提供了新的见解。

  DOI：

  10.1248/cpb.52.204
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 氢溴酸 、 溶剂黄146 、 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， 生成 PheA6
  参考文献：
  名称：

  A simple peptidomimetic that self-associates on the solid state to form a nanoporous architecture containing chiral π-channels

  摘要：

  源自苯丙氨酸的简单拟肽化合物晶体结构显示，形成了包含一维π通道的纳米多孔结构，其中芳香环作为手性通道壁的唯一组分。

  DOI：

  10.1039/b922172g

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。
• Acyclic Pseudopeptidic Hosts as Molecular Receptors and Transporters for Anions
  作者：Inés Martí、M. Isabel Burguete、Philip A. Gale、Santiago V. Luis

  DOI：10.1002/ejoc.201500390

  日期：2015.8

  The synthesis and characterization of different pseudopeptidic hosts derived from open chain systems with C2 and C3 symmetry has been achieved. These receptors are based on structures containing phenylalanine amino acid residues and amine, amide, urea and thiourea groups as the structural elements providing their capability to interact with anions. The transport of chloride and organic anions of biological

  已经实现了源自具有 C2 和 C3 对称性的开链系统的不同拟肽宿主的合成和表征。这些受体基于包含苯丙氨酸残基和胺、酰胺、脲和硫脲基团作为结构元素的结构，提供它们与阴离子相互作用的能力。已经针对这些受体研究了氯离子和具有生物相关性的有机阴离子（L-乳酸、L-马来酸和 L-天冬氨酸）通过脂质双层膜的转运。已通过 NMR 滴定在溶液中研究了所选主体的氯化物结合特性。此外，为了使结果合理化，还​​进行了亲脂性研究。已经观察到运输活性受脂肪族中央间隔基和侧链的性质影响，最活跃的受体是 9b，源自具有最短脂肪族侧链的三足前体和 3c，源自双（氨基酰胺）但具有最长的间隔区。与研究的有机阴离子相比，这些主体对氯化物阴离子更具选择性。
• <scp>l</scp>-Phenylalanine-derived pseudopeptidic bioinspired materials: Zn(<scp>ii</scp>) induced fluorescence enhancement and precise tuning of self-assembled nanostructures
  作者：Kamlesh Kumar Nigam、Arpna Tamrakar、Mrituanjay D. Pandey

  DOI：10.1039/d3sm00703k

  日期：——

  C ₂-Symmetric pseudopeptides has been developed for Zn(ii) guided fluorescence enhancement and nono-strutural modifications.

  C 2 对称伪肽，用于 Zn(ii) 引导的荧光增强和非结构修饰。
• Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acids
  作者：Belén Altava、M. Isabel Burguete、Noèlia Carbó、Jorge Escorihuela、Santiago V. Luis

  DOI：10.1016/j.tetasy.2010.05.010

  日期：2010.4

  A family of bis(amino amides) derived from natural amino acids has been synthesized and tested for the NMR enantiodiscrimination, as chiral solvating agents, for enantiomeric excess determination of some carboxylic acids. Those bis(amino amide) receptors contain different structural modifications and the splitting of the signals of the acids, after addition of the corresponding CSAs, depends on those structural variables. The influence of aminoacid side chain and the nature of the aliphatic spacer are important parameters to obtain good chiral discriminations. The results obtained clearly show the chiral recognition abilities of these bis(amino amide) ligands and suggest their advantageous use as chiral solvating agents for carboxylic acids. The binding between bis(amino amides) and carboxylic acids has been studied by ESI-MS, NMR, DSC, and molecular modeling. The data suggest that enantiodiscrimination involves the formation of an ionic pair after proton transfer from the carboxylic substrate to the bis(amino amides). (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and organogelating ability of bis-urea pseudopeptidic compounds
  作者：Jenifer Rubio、Vicente Martí-Centelles、M. Isabel Burguete、Santiago V. Luis

  DOI：10.1016/j.tet.2013.01.007

  日期：2013.3

  A large family of amphiphilic pseudopeptidic derivatives in which the aliphatic tails are connected to the pseudopeptidic moiety through urea functionalities have been prepared with excellent yields. The synthetic procedure is simple and very efficient and allows a modular variation of a large number of structural parameters. The self-assembling properties of the resulting compounds has been studied under different conditions and using different media. Very interestingly, many of the compounds obtained have revealed to act as very efficient organogelators at low concentrations. The resulting gels provide some unusual properties. Of particular relevance are the broad scope of organic solvents that can be gelated and the high thermal stability of the resulting gels. Gels that are stable up to temperatures close to 100 degrees C can be obtained in some instances. (C) 2013 Elsevier Ltd. All rights reserved.