L-Phe-D-Leu-OCH3 trifluoroacetate | 83588-10-7

• 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: L-Phe-D-Leu-OCH3 trifluoroacetate
• CAS: 83588-10-7
• 化学式: C₂HF₃O₂*C₁₆H₂₄N₂O₃
• 分子量: 406.402
• InChiKey: JNLWQRYNGNLIRC-LMRHVHIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118.72
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  溴乙酸乙酯 、 L-Phe-D-Leu-OCH3 trifluoroacetate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 12.0h， 以50%的产率得到N-(carbethoxymethyl)-L-phenylalanyl-D-leucine methyl ester
  参考文献：
  名称：

  脑脑啡肽酶的新型羧烷基抑制剂：合成，生物活性和止痛特性。

  摘要：

  合成了衍生自Phe-Leu和Phe-Ala的新羧烷基化合物，并将其作为“脑啡肽酶”的抑制剂进行检查，这是一种从小鼠纹状体膜上裂解脑啡肽的Gly3-Phe4键的金属内肽酶。这些羧烷基化合物对脑脑啡肽酶和血管紧张素转化酶（ACE）催化位点的差异识别会导致脑啡肽降解酶的有效抑制剂（KI约为0.5 microM），竞争性和选择性抑制剂。最有趣的化合物N-[（（RS）-2-羧基-3-苯基丙酰基] -L-亮氨酸（3，KI = 0.34 microM））对脑啡肽酶的效力是ACE活性的10000倍。小鼠脑室内（icv）注射3可以增强外源性D-Ala2-Met-脑啡肽的镇痛作用，证明体内对脑啡肽酶的抑制作用。而且，单独给予icv 3可以在热板试验和扭体试验中测出小鼠的剂量依赖性镇痛作用。在以前的分析中，每只动物的ED50约为10微克，略高于硫醇。纳洛酮拮抗了所有的抗伤害感受作用，表明脑啡肽参与了镇痛作用，并

  DOI：

  10.1021/jm00355a013
• 作为产物：
  描述：

  Boc-Phe-O-COO-isoBu 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 L-Phe-D-Leu-OCH3 trifluoroacetate
  参考文献：
  名称：

  Efficient and Highly Selective Copper(II) Transport across a Bulk Liquid Chloroform Membrane Mediated by Lipophilic Dipeptides

  摘要：

  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.

  DOI：

  10.1021/jo9703257