Fmoc-Phe-Tyr-OH

• 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: Fmoc-Phe-Tyr-OH
• 英文别名: (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
• 化学式: C₃₃H₃₀N₂O₆
• 分子量: 550.611
• InChiKey: IUXBXIFLXBWHHS-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Fmoc-Phe-Tyr-OMe 在 subtilisin from Bacillus licheniformis 、 水 作用下， 反应 1.33h， 生成 Fmoc-Phe-Tyr-OH
  参考文献：
  名称：

  Biocatalytic induction of supramolecular order

  摘要：

  超分子凝胶具有可调功能，在医疗保健、环境保护和能源相关技术等多个领域备受关注。以可靠的方式制备这些材料具有挑战性，因为在较高的自组装速率下会观察到更多的动力学缺陷。在这里，通过将生物催化与分子自组装相结合，我们展示了更快获得更高有序结构的能力。只需增加酶的浓度，分子、纳米和微米级的超分子有序性就会显著增强，重要的是，凝胶剂的浓度保持不变。双亲分子的制备方法是在二肽骨架上连接一个芳香分子，并以甲酯封顶。它们的自组装是由一种水解酯的酶诱导的。不同浓度的酶会改变酶簇的催化活性和大小，从而影响其流动性。这样，就可以根据单一凝胶体结构获得结构多样的材料，这些材料代表了自由能图谱中的局部最小值。超分子凝胶在医疗保健和能源技术等多个领域都大有可为，因为其可调特性直接来源于其构建模块的组织。现在，研究人员已经能够通过将酶催化与分子自组装相结合来控制这种行为。虽然这似乎有违直觉，但组装速度更快的凝胶显示出更少的缺陷。

  DOI：

  10.1038/nchem.861

文献信息

• Efficient and facile formation of two-component nanoparticles via aromatic moiety directed self-assembly
  作者：Weiping Wang、Ying Chau

  DOI：10.1039/c1cc11048a

  日期：——

  Here we present a two-component self-assembling system employing the interaction of aromatic groups (Fmoc) to construct nanoparticles. Spherical particles of around 70 nm were formed spontaneously by a simple trigonal Fmoc-conjugate, which were then stabilized by Fmoc-dipeptides at physiological pH in aqueous solution. These novel particles, being well-tolerated by cells, capable of encapsulating hydrophobic compounds, and readily decorated by short peptides, are promising carriers for drug delivery.

  这里我们介绍一个利用芳香基团（Fmoc）相互作用构建纳米颗粒的两部分自组装系统。由一个简单的三配位Fmoc-偶联物自发形成的约70 nm的球形颗粒，在水溶液中生理pH下通过Fmoc-二肽得到稳定。这些新型颗粒，由于对细胞无害，能封装疏水性化合物，并可通过短肽进行简单修饰，因此是很有前景的药物输送载体。
• Enzyme Instructed Self‐assembly of Naphthalimide‐dipeptide: Spontaneous Transformation from Nanosphere to Nanotubular Structures that Induces Hydrogelation
  作者：Rajan Deepan Chakravarthy、Mohiuddin Mohammed、Hsin‐Chieh Lin

  DOI：10.1002/asia.202000575

  日期：2020.9

  subsequently resulted in hydrogelation. The self‐assembly is driven by the formation of β‐sheet type structures stabilized by offset aromatic stacking of NI core and hydrogen bonding interactions which is confirmed with PXRD, Congo‐red staining and molecular mechanical calculations. We propose a mechanism for the self‐assembly process based on TEM and spectroscopic data. The nanotubular structures of NI‐FYp precursor

  了解自组装纳米结构的结构形态关系对于开发具有所需化学和生物学功能的材料至关重要。在此，首次开发了基于磷酸盐的萘二甲酰亚胺（NI）衍生物，以研究酶指导的自组装过程。简单氨基酸衍生物NI-Y p的自组装会在碱性磷酸酶存在的情况下产生非特异性的无定形聚集体。另一方面，NI‐FY p二肽在水性条件下形成球形纳米颗粒，在酶催化过程中通过多个阶段缓慢转变为部分未压缩的纳米管结构，随后导致水凝胶化。自组装是由β片型结构的形成驱动的，该结构通过NI核的偏移芳族堆积和氢键相互作用而得以稳定，这已通过PXRD，刚果红染色和分子力学计算得到了证实。我们提出了一种基于TEM和光谱数据的自组装过程的机制。NI‐FY p的纳米管结构与类似的Fmoc衍生物的纳米纤维结构相比，前体对人乳腺癌细胞和人宫颈癌细胞具有更高的细胞毒性。总体而言，这项研究为小分子水凝胶剂的超分子自组装提供了新的认识。
• Micelle to fibre biocatalytic supramolecular transformation of an aromatic peptide amphiphile
  作者：Jan W. Sadownik、Joy Leckie、Rein V. Ulijn

  DOI：10.1039/c0cc03796f

  日期：——

  We use a range of spectroscopic methods to provide mechanistic insight into a phosphatase-driven supramolecular transformation whereby an amphiphilic peptide building block, upon dephosphorylation, switches from a solution-phase, micellar structure to a gel-phase, chiral uni-directional nanofibre morphology.

  我们利用一系列光谱学方法，从机理上揭示了磷酸酶驱动的超分子转化过程，即两亲肽结构单元在去磷酸化后，从溶液相胶束结构转变为凝胶体相手性单向纳米纤维形态。
• Suresh Babu, Vommina V.; Ramana Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 11, p. 2328 - 2332
  作者：Suresh Babu, Vommina V.、Ramana Rao

  DOI：——

  日期：——
• Biocatalytic induction of supramolecular order
  作者：Andrew R. Hirst、Sangita Roy、Meenakshi Arora、Apurba K. Das、Nigel Hodson、Paul Murray、Stephen Marshall、Nadeem Javid、Jan Sefcik、Job Boekhoven、Jan H. van Esch、Stefano Santabarbara、Neil T. Hunt、Rein V. Ulijn

  DOI：10.1038/nchem.861

  日期：2010.12

  Supramolecular gels, which demonstrate tunable functionalities, have attracted much interest in a range of areas, including healthcare, environmental protection and energy-related technologies. Preparing these materials in a reliable manner is challenging, with an increased level of kinetic defects observed at higher self-assembly rates. Here, by combining biocatalysis and molecular self-assembly, we have shown the ability to more quickly access higher-ordered structures. By simply increasing enzyme concentration, supramolecular order expressed at molecular, nano- and micro-levels is dramatically enhanced, and, importantly, the gelator concentrations remain identical. Amphiphile molecules were prepared by attaching an aromatic moiety to a dipeptide backbone capped with a methyl ester. Their self-assembly was induced by an enzyme that hydrolysed the ester. Different enzyme concentrations altered the catalytic activity and size of the enzyme clusters, affecting their mobility. This allowed structurally diverse materials that represent local minima in the free energy landscape to be accessed based on a single gelator structure. Supramolecular gels show promise in diverse areas, including healthcare and energy technologies, owing to tunable properties that arise directly from the organization of their building blocks. Researchers have now been able to control this behaviour by combining enzymatic catalysis with molecular self-assembly. Although it seems counter-intuitive, gels that assembled faster showed fewer defects.

  超分子凝胶具有可调功能，在医疗保健、环境保护和能源相关技术等多个领域备受关注。以可靠的方式制备这些材料具有挑战性，因为在较高的自组装速率下会观察到更多的动力学缺陷。在这里，通过将生物催化与分子自组装相结合，我们展示了更快获得更高有序结构的能力。只需增加酶的浓度，分子、纳米和微米级的超分子有序性就会显著增强，重要的是，凝胶剂的浓度保持不变。双亲分子的制备方法是在二肽骨架上连接一个芳香分子，并以甲酯封顶。它们的自组装是由一种水解酯的酶诱导的。不同浓度的酶会改变酶簇的催化活性和大小，从而影响其流动性。这样，就可以根据单一凝胶体结构获得结构多样的材料，这些材料代表了自由能图谱中的局部最小值。超分子凝胶在医疗保健和能源技术等多个领域都大有可为，因为其可调特性直接来源于其构建模块的组织。现在，研究人员已经能够通过将酶催化与分子自组装相结合来控制这种行为。虽然这似乎有违直觉，但组装速度更快的凝胶显示出更少的缺陷。