methyl-(N-Boc-L-phenylalanine)-D-leucinate | 99597-71-4

• 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: methyl-(N-Boc-L-phenylalanine)-D-leucinate
• 英文别名: t-Boc-Phe-D-Leu-OMe；Boc-L-Phe-D-Leu-CO2CH3；Boc-Phe-D-Leu-OMe；methyl (2R)-4-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]pentanoate
• CAS: 99597-71-4
• 化学式: C₂₁H₃₂N₂O₅
• 分子量: 392.495
• InChiKey: NUKWPDXDMGXCBV-DLBZAZTESA-N

物化性质

• 熔点：
  136-138 °C
• 沸点：
  551.1±50.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  methyl-(N-Boc-L-phenylalanine)-D-leucinate 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 生成
  参考文献：
  名称：

  C- and N-terminal residue effect on peptide derivatives' antagonism toward the formyl-peptide receptor

  摘要：

  The biological action of several X-Phe-D-Leu-Phe-D-Leu-Z (X=3',5'-dimethylphenyl-ureido; Z=Phe, Lys, Glu, Tyr) analogues was analysed on human neutrophils to evaluate their ability to antagonize formyl-peptide receptors. X-Phe-D-Leu-Phe-D-Leu-Phe analogues obtained as C-terminal olo or amido derivatives and T-Phe-D-Leu-Phe-D-Leu-Phe analogues (T=thiazolyl-ureido) were also analysed. The activities of pentapeptide derivatives were compared with those of X-Phe-D-Leu-Phe-D-Leu-Phe chosen as reference antagonist. Our results demonstrate that X-Phe-D-Leu-Phe-D-Leu-Phe-olo, X-Phe-D-Leu-Phe-D-Leu-Glu and X-Phe-D-Leu-Phe-D-Leu-Tyr are more active antagonists than X-Phe-D-Leu-Phe-D-Leu-Phe. The presence of Lys (X-Phe-D-Leu-Phe-D-Leu-Lys) seems, instead, to inhibit the formyl-peptide receptor antagonist properties. The presence of the N-terminal thiazolyl-ureido group seems to considerably contribute to the receptor antagonist properties of T-Phe-D-Leu-Phe-D-Leu-Phe-OH. The introduction of the C-terminal methyl ester (T-Phe-D-Leu-Phe-D-Leu-Phe-OMe) or amido group (X-Phe-D-Leu-Phe-D-Leu-Phe-NH2) appears detrimental for the affinity and formyl-peptide receptor antagonist properties of the Phe-D-Leu-Phe-D-Leu-Phe derivatives. The examined peptides inhibit superoxide anion production and lysozyme release more efficaciously than neutrophil chemotaxis. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0014-2999(01)01627-2
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.05h， 生成 methyl-(N-Boc-L-phenylalanine)-D-leucinate
  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

文献信息

• A Novel and Efficient Method for Cleavage of Phenacylesters by Magnesium Reduction with Acetic Acid
  作者：Stella Kokinaki、Leondios Leondiadis、Nikolas Ferderigos

  DOI：10.1021/ol050209n

  日期：2005.4.1

  [reaction: see text] In the present study, we use magnesium turnings as a new deprotection reagent for the phenacyl group during orthogonal organic synthesis in the presence of other esters and sensitive protecting groups. By applying the new magnesium turnings/acetic acid deprotection method, phenacyl group can be more easily combined with other protecting groups that are not compatible with the zinc/acetic

  [反应：见正文]在本研究中，我们在其他酯类和敏感保护基团存在的情况下，在正交有机合成过程中，使用镁屑作为苯甲酰基的新型去保护剂。通过应用新的镁屑/乙酸脱保护方法，可以使苯甲酰基与不兼容锌/乙酸方法的其他保护基结合。
• Solid-Phase Synthesis of Lipidated Ras Peptides Employing the Ellman Sulfonamide Linker
  作者：Gemma Triola、Marc Gerauer、Kristina Görmer、Lucas Brunsveld、Herbert Waldmann

  DOI：10.1002/chem.201001642

  日期：2010.8.16

  A detailed study on the solid‐phase synthesis of lipidated peptides of the Ras family employing the Ellman sulfonamide linker is reported. Using the C‐terminal N‐Ras sequence, critical issues such as lipidated amino acid resin loading, peptide elongation in the presence of labile groups and optimized conditions for release of the peptides were investigated. A versatile methodology for the synthesis

  报告了使用Ellman磺酰胺接头对Ras家族的脂化肽进行固相合成的详细研究。使用C端N-Ras序列，研究了关键问题，例如脂化氨基酸树脂的上样量，在不稳定基团存在下的肽伸长以及优化的肽释放条件。因此，已经建立了一种合成具有多种脂质基序和C端甲基酯的肽的通用方法。
• Activation Method to Prepare a Highly Reactive Acylsulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis¹
  作者：Bradley J. Backes、Alex A. Virgilio、Jonathan A. Ellman

  DOI：10.1021/ja9535165

  日期：1996.1.1
• 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.
• C- and N-terminal residue effect on peptide derivatives' antagonism toward the formyl-peptide receptor
  作者：Alessandro Dalpiaz、Maria E. Ferretti、Gianni Vertuani、Serena Traniello、Angelo Scatturin、Susanna Spisani

  DOI：10.1016/s0014-2999(01)01627-2

  日期：2002.2

  The biological action of several X-Phe-D-Leu-Phe-D-Leu-Z (X=3',5'-dimethylphenyl-ureido; Z=Phe, Lys, Glu, Tyr) analogues was analysed on human neutrophils to evaluate their ability to antagonize formyl-peptide receptors. X-Phe-D-Leu-Phe-D-Leu-Phe analogues obtained as C-terminal olo or amido derivatives and T-Phe-D-Leu-Phe-D-Leu-Phe analogues (T=thiazolyl-ureido) were also analysed. The activities of pentapeptide derivatives were compared with those of X-Phe-D-Leu-Phe-D-Leu-Phe chosen as reference antagonist. Our results demonstrate that X-Phe-D-Leu-Phe-D-Leu-Phe-olo, X-Phe-D-Leu-Phe-D-Leu-Glu and X-Phe-D-Leu-Phe-D-Leu-Tyr are more active antagonists than X-Phe-D-Leu-Phe-D-Leu-Phe. The presence of Lys (X-Phe-D-Leu-Phe-D-Leu-Lys) seems, instead, to inhibit the formyl-peptide receptor antagonist properties. The presence of the N-terminal thiazolyl-ureido group seems to considerably contribute to the receptor antagonist properties of T-Phe-D-Leu-Phe-D-Leu-Phe-OH. The introduction of the C-terminal methyl ester (T-Phe-D-Leu-Phe-D-Leu-Phe-OMe) or amido group (X-Phe-D-Leu-Phe-D-Leu-Phe-NH2) appears detrimental for the affinity and formyl-peptide receptor antagonist properties of the Phe-D-Leu-Phe-D-Leu-Phe derivatives. The examined peptides inhibit superoxide anion production and lysozyme release more efficaciously than neutrophil chemotaxis. (C) 2002 Elsevier Science B.V. All rights reserved.