Phe-Phe-OEt | 67247-04-5

• 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: Phe-Phe-OEt
• 英文别名: N-L-phenylalanyl-L-phenylalanine ethyl ester；N-L-Phenylalanyl-L-phenylalanin-aethylester；ethyl (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoate
• CAS: 67247-04-5
• 化学式: C₂₀H₂₄N₂O₃
• 分子量: 340.422
• InChiKey: QEAKCFKVHVDYLV-ROUUACIJSA-N

物化性质

• 熔点：
  246-248 °C
• 沸点：
  542.7±50.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Phe-Phe-OEt 在 水 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 (S)-N-((5R,14S,17S)-14-benzyl-1-(4-methoxyphenyl)-4,7,10,13,16-pentaoxo-18-phenyl-5-((tritylthio)methyl)-2,3,6,9,12,15-hexaazaoctadec-1-en-17-yl)-4-methyl-2-((S)-2-pivalamidopropanamido)pentanamide
  参考文献：
  名称：

  Efficient Assembly of Threaded Molecular Machines for Sequence-Specific Synthesis

  摘要：

  We report on an improved strategy for the preparation of artificial molecular machines that can pick up and assemble reactive groups in sequence by traveling along a track. In the new approach a preformed rotaxane synthon is attached to the end of an otherwise fully formed strand of building blocks. This "rotaxane-capping" protocol is significantly more efficient than the "final-step-threading" method employed previously and enables the synthesis of threaded molecular machines that operate on extended oligomer, and potentially polymer, tracks. The methodology is exemplified through the preparation of a machine that adds four amino acid building blocks from a strand in sequence, featuring up to 20-membered ring native chemical ligation transition states.

  DOI：

  10.1021/ja5022415
• 作为产物：
  描述：

  Z-Phe-Phe-OEt 在 氢气 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以100%的产率得到Phe-Phe-OEt
  参考文献：
  名称：

  聚氯乙烯负载的钯纳米粒子：快速氢化反应的催化剂†

  摘要：

  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。

  DOI：

  10.1039/c0ob00962h

文献信息

• 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.
• Efficient and Highly Selective Copper(II) Transport across a Bulk Liquid Chloroform Membrane Mediated by Lipophilic Dipeptides
  作者：Marco C. Cleij、Paolo Scrimin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1021/jo9703257

  日期：1997.8.1

  Several structurally simple N-monoalkylated and -dialkylated dipeptides made of alpha-amino acids Gly, Phe, and Leu, 1-11, were synthesized and investigated as carriers for the transport of Cu(II), Zn(II), and Ni(II) from an aqueous pH = 5.6 buffer source to a 0.1 M HCl receiving phase across a bulk chloroform membrane. The proton-driven translocation was followed during the process by analyzing the metal ion concentrations in the three phases. The transport efficiency depends on the ease of formation of a neutral complex with Cu(II) (the peptide group and carboxylic acid being deprotonated) at the source-chloroform interface and on that of its disruption by protonation at the receiving phase: the carrier's Lipophilicity favors the metal ion uptake and not the release. By modulating the length of the N-alkyl chains and the hydrophobicity of the dipeptide moiety, a quite remarkable transport efficiency was observed for Cu(II), in most cases superior to that of the industrial extractant Kelex 100. Moreover, using L,L- and L,D-N-octyl-PheLeu as carriers, remarkable diastereomeric effects were observed in the rate of uptake and release of Cu(II) ion although the differences mutually compensate in the overall transport rate. Under the conditions used the carriers are much less effective in the translocation of Zn(II) and Ni(II) and their transport efficiency drops dramatically in the presence of Cu(II), the latter being favored by factors of 1.2 x 10(3) and > 10(4), respectively. Such very high selectivities depend on the fact that only Cu(II) among other transition metal ions Can form neutral complexes at the pH value of the source phase.
• Removal of benzyl-type protecting groups from peptides by catalytic transfer hydrogenation with formic acid
  作者：Babiker ElAmin、Gattadahalli M. Anantharamaiah、Garfield P. Royer、Gary E. Means

  DOI：10.1021/jo01333a048

  日期：1979.9
• Phenylalanylphenylalanine Ethyl Ester Synthesis by Chymotrypsin
  作者：Henry Tauber

  DOI：10.1021/ja01123a524

  日期：1952.2
• 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。