Z-Phe-Phe-OEt | 5276-63-1

• 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: Z-Phe-Phe-OEt
• 英文别名: Z-L-Phe-L-Phe-OEt；ethyl (2S)-3-phenyl-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 5276-63-1
• 化学式: C₂₈H₃₀N₂O₅
• 分子量: 474.557
• InChiKey: KHTAROPAVLHHKM-DQEYMECFSA-N

物化性质

• 熔点：
  1336-1345 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  694.4±55.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Phe-Phe-OEt 在 甲醇 、 氨 作用下， 生成 Cbz-L-Phe-L-Phe-NH2
  参考文献：
  名称：

  Fruton; Bergmann, Journal of Biological Chemistry, 1942, vol. 145, p. 253,260

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 六甲基二硅氧烷 、 1-羟基苯并三唑 、 4-甲苯硫酚 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 86.0h， 生成 Z-Phe-Phe-OEt
  参考文献：
  名称：

  HMDO-Promoted Peptide and Protein Synthesis in Ionic Liquids

  摘要：

  Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.

  DOI：

  10.1021/jo400797t

文献信息

• Poly(vinyl)chloride supported palladium nanoparticles: catalyst for rapid hydrogenation reactions
  作者：Hosahalli P. Hemantha、Vommina V. Sureshbabu

  DOI：10.1039/c0ob00962h

  日期：——

  Palladium nanoparticles supported over poly(vinyl)chloride matrix (PVC-Pd0) are prepared through an efficient and inexpensive protocol. The catalyst has been characterized by XRD, SEM and TEM and its utility for the reduction of a range of functional groups as well as for the removal of some common protecting groups employed in peptide chemistry is demonstrated.

  通过高效且廉价的方案制备了负载在聚氯乙烯基质（PVC-Pd 0）上的钯纳米颗粒。该催化剂已通过XRD，SEM和TEM进行了表征，并证明了其在还原一系列官能团以及去除某些在肽化学中使用的常见保护基的实用性。
• High isolated yields in thermodynamically controlled peptide synthesis in toluene catalysed by thermolysin adsorbed on Celite R-640
  作者：Alessandra Basso、Luigi De Martin、Cynthia Ebert、Lucia Gardossi、Paolo Linda

  DOI：10.1039/b000797h

  日期：——

  An innovative immobilisation method that allows peptide synthesis to be performed even at equimolar concentrations, by controlling water activity, is reported.

  报道了一种创新的固定化方法，该方法通过控制水活性，即使在等摩尔浓度下也能进行肽合成。
• Aminosäuren und Peptide, XIII. Darstellung aktiver Pyridyl-(3)-ester N-geschützter Aminosäuren und Peptide sowie deren Anwendung zur Peptid-Synthese
  作者：Emil Taschner、Barbara Rzeszotarska、Lucja Lubiewska

  DOI：10.1002/jlac.19656900117

  日期：1965.1

  Pyridyl-(3)-ester N-geschützter Aminosäuren bzw. Peptide (Tab. 1) werden mittels 3-Hydroxypyridins bevorzugt nach der Dicyclohexylcarbodiimid-Methode dargestellt und mit Aminosäureestern in die entsprechenden N-geschützten Peptidester (Tab. 2) verwandelt.

  N-保护的氨基酸或肽（表1）的吡啶基（3）酯优选使用二羟基己基碳二亚胺方法使用3-羟基吡啶制备，并与氨基转化为相应的N-保护的肽酯（表2）。酸酯。
• Copper-Catalyzed Construction of Amide Linkages via Coupling between Unactivated Acids and Amines
  作者：Sukalyan Bhadra、Ajijur Rahaman

  DOI：10.1055/a-2145-5986

  日期：2023.12

  Traditional amide linkage forming reactions by the coupling between an acid and an amine rely primarily on triggering the carboxylic acid counterpart with (over)stoichiometric activating agent(s) and generate unacceptable quantity of nondisposable waste, leading to poor atom economy. Herein, we report an efficient catalytic amide synthesis that proceeds through the in situ activation of the amine counterpart

  传统的通过酸和胺之间的偶联形成酰胺键的反应主要依赖于用（超过）化学计量的活化剂触发羧酸对应物，并产生数量不可接受的不可处理废物，导致原子经济性差。在此，我们报道了一种有效的催化酰胺合成方法，该合成方法通过活性N-甲酰胺物种形式的胺对应物的原位活化进行。该策略可以方便地从多种类型的酸和胺中获取一系列结构不同的酰胺，包括二肽，而不产生化学计量的固体废物。
• Structure–activity study of endomorphin-2 analogs with C-terminal modifications by NMR spectroscopy and molecular modeling
  作者：Chang-lin Wang、Jin-long Yao、Ye Yu、Xuan Shao、Yun Cui、Hong-mei Liu、Lu-hao Lai、Rui Wang

  DOI：10.1016/j.bmc.2008.05.001

  日期：2008.6

  Endomorphin-2 (EM-2) is a putative endogenous mu-opioid receptor ligand. To get insight into the important role of C-terminal amide group of EM-2, we investigated herein a series of EM-2 analogs by substitution of the C-terminal amide group with -NHNH2, -NHCH3, -N(CH3)(2), -OCH3, -OCH2CH3, -OC(CH3) 3, and -CH2 -OH. Their binding affinity and bioactivity were determined and compared. Despite similar (analogs 1, 4, and 7) or decreased (analogs 2, 3,5, and 6) mu affinity in binding assays, all analogs showed low guinea pig ileum (GPI) and mouse vas deferens (MVD) potencies compared to their parent peptide. Interestingly, as for analogs 2 and 3 (a single and double N-methylation of C-terminal amide), the potency order with the K-i (mu) values was 2 > 3; for the C-terminal esterified analogs 4 -6, the potency order with the Ki (mu) values was 4 > 5 > 6. Thus, we concluded that the steric hindrance of C-terminus might play an important role in opioid receptor affinity. We further investigated the conformational properties of these analogs by 1D and 2D H-1 NMR spectroscopy and molecular modeling. Evaluating the ratios of cis-and trans-isomers, aromatic interactions, dihedral angles, and stereoscopic views of the most convergent conformers, we found that modi. cations at the C-terminal amide group of EM-2 affected these analog conformations markedly, therefore changed the opioid receptor affinity and in vitro bioactivity. (c) 2008 Elsevier Ltd. All rights reserved.

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