Fmoc-L-Trp-L-Phe-OCH₃ | 1227608-50-5

• 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: Fmoc-L-Trp-L-Phe-OCH₃
• 英文别名: Fmoc-Trp-Phe-OMe
• CAS: 1227608-50-5
• 化学式: C₃₆H₃₃N₃O₅
• 分子量: 587.675
• InChiKey: APPGPUXYFKTMTH-LQJZCPKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  109.52
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  对氟苯硫酚 、 Fmoc-L-Trp-L-Phe-OCH₃ 在 lithium perchlorate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 以76.1 %的产率得到methyl ((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(2-((4-fluorophenyl)thio)-1H-indol-3-yl)propanoyl)-L-phenylalaninate
  参考文献：
  名称：

  色氨酸残基的电化学生物共轭：肽修饰的策略

  摘要：

  人们对电催化生物共轭反应的兴趣激增，特别是对于修饰蛋白质中的色氨酸和酪氨酸残基。我们使用经济高效的石墨毡电极和低电流方法实现了色氨酸与苯硫酚的选择性生物共轭，产率高达 92%。该方法专门标记色氨酸残基并掺入氟化色氨酸用于 NMR 分析。包括兰瑞肽和亮丙瑞林在内的八种多肽被有效偶联，证明了该方法的多功能性以及作为新型诊断和治疗剂的潜力。

  DOI：

  10.1021/acs.orglett.4c01662
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 、 Fmoc-L-色氨酸(Boc)-OH 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 Fmoc-L-Trp-L-Phe-OCH₃
  参考文献：
  名称：

  色氨酸残基的电化学生物共轭：肽修饰的策略

  摘要：

  人们对电催化生物共轭反应的兴趣激增，特别是对于修饰蛋白质中的色氨酸和酪氨酸残基。我们使用经济高效的石墨毡电极和低电流方法实现了色氨酸与苯硫酚的选择性生物共轭，产率高达 92%。该方法专门标记色氨酸残基并掺入氟化色氨酸用于 NMR 分析。包括兰瑞肽和亮丙瑞林在内的八种多肽被有效偶联，证明了该方法的多功能性以及作为新型诊断和治疗剂的潜力。

  DOI：

  10.1021/acs.orglett.4c01662

文献信息

• A multicomponent reaction for modular assembly of indole-fused heterocycles
  作者：Jiaming Li、Hao Ni、Weiwei Zhang、Zhencheng Lai、Huimin Jin、Linwei Zeng、Sunliang Cui

  DOI：10.1039/d4sc00522h

  日期：——

  discovery. Indole-fused heterocycles, particularly seven-membered ones, have received increasing attention due to their distinctive chemical characteristics and wide spectrum of bioactivities. However, the synthetic access to these compounds is highly limited. Herein, we report a unique multicomponent reaction (MCR) for modular assembly of indole-fused seven-membered heterocycles. In this process, indole

  吲哚是天然产物和药物发现中的特殊化学实体。吲哚稠合杂环，特别是七元杂环，由于其独特的化学特性和广泛的生物活性而受到越来越多的关注。然而，这些化合物的合成途径非常有限。在此，我们报告了一种独特的多组分反应（MCR），用于吲哚稠合七元杂环的模块化组装。在此过程中，吲哚、甲醛和氨基盐酸盐可以快速组装生成吲哚稠合的恶二氮卓类药物，再添加硫代硫酸钠将得到吲哚稠合的硫二氮卓类药物。生物学评价揭示了这些化合物具有良好的抗癌活性。此外，该MCR可应用于肽的后期和选择性修饰。因此，这项工作为吲哚功能化提供了强大的策略，并为构建七元杂环提供了宝贵的工具。
• Scalable Total Syntheses of <i>N</i>-Linked Tryptamine Dimers by Direct Indole−Aniline Coupling: Psychotrimine and Kapakahines B and F
  作者：Timothy Newhouse、Chad A. Lewis、Kyle J. Eastman、Phil S. Baran

  DOI：10.1021/ja1009458

  日期：2010.5.26

  This report details the invention of a method to enable syntheses of psychotrimine (1) and the kapakahines F and B (2, 3) on a gram scale and in a minimum number of steps. Mechanistic inquiries are presented for the key enabling quaternization of indole at the C3 position by electrophilic attack of an activated aniline species. Excellent chemo-, regio-, and diastereoselectivities are observed for reactions with o-iodoaniline, an indole cation equivalent. Additionally, the scope of this reaction is broad with respect to the tryptamine and aniline components. The anti-cancer profiles of 1-3 have also been evaluated.
• Self-assembled dipeptide nanospheres as single component based delivery vehicle for ampicillin and doxorubicin
  作者：Prabhjot Singh、Priya Manhas、Rohit Sharma、Satish K. Pandey、Rohit K. Sharma、Om P. Katare、Nishima Wangoo

  DOI：10.1016/j.molliq.2020.113420

  日期：2020.8

  Effective delivery of therapeutic agents encounters many challenges such as uncontrolled drug release, low bioavailability of drugs, degradation of drugs in the intestinal transit and non-biocompatibility of the delivery vehicle. Thus, in the quest for advance drug delivery system, self-assembled dipeptide (Frnoc-L-Trp-L-Phe-OCH3) nanospheres (SPNS) were generated in aqueous medium with size ranging between 100 and 400 nm. The SPNS were examined for the presence of hydrophobic and hydrophilic domains which was followed by drug loading analysis (ampicillin and doxorubicin) into SPNS using HPLC. Further, SPNS demonstrated pH triggered morphological alterations leading to controlled release of loaded therapeutics. Additionally, SPNS exhibited low cytotoxicity and exceptional stability against enzymatic degradation. The system was further analyzed for in vitro cellular internalization of therapeutics. Thus, outcome of this analysis indicated that SPNS acts as single component, multifunctional drug delivery vehicle by addressing critical issues such as effective drug loading, pH responsive controlled release, biocompatibility, and stability against enzymatic degradation. (C) 2020 Published by Elsevier B.V.