2,5-吡咯烷二酮,1-[[N-[(1,1-二甲基乙氧基)羰基]-L-苯基丙氨酰-L-苯基丙氨酰]氧代]- | 189062-72-4

• 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
• 中文名称: 2,5-吡咯烷二酮,1-[[N-[(1,1-二甲基乙氧基)羰基]-L-苯基丙氨酰-L-苯基丙氨酰]氧代]-
• 英文名称: Boc-Phe-Phe-OSu
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoate
• CAS: 189062-72-4
• 化学式: C₂₇H₃₁N₃O₇
• 分子量: 509.559
• InChiKey: MSUWZAWSQSKMSF-SFTDATJTSA-N

物化性质

• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-吡咯烷二酮,1-[[N-[(1,1-二甲基乙氧基)羰基]-L-苯基丙氨酰-L-苯基丙氨酰]氧代]- 在 盐酸 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 N¹,N²-bis(L-Phe-L-Phe)ethanediamine
  参考文献：
  名称：

  Spacer driven morphological twist in Phe-Phe dipeptide conjugates

  摘要：

  Chemists and material scientists are interested in complex biological systems and morphologies for fabrication of new materials. Bioinspired design of short peptide conjugates produces various self-assembled structures, depending on their structural diversity. Phe-Phe aromatic dipeptide is an interesting candidate for designing variety of molecular scaffolds. This report describes the synthesis of two symmetrical peptide conjugates by a coupling with C2 and C3 symmetric functional linker's, which spontaneously generate different self-assembled ultra-structures. C2 Symmetric, ethylene diamine linker, conjugated two Phe-Phe dipeptides and produced Phe-Phe-EDA-Phe-Phe (5), which undergoes spontaneous self-assembly to form fibrillar morphology, while C3 symmetric tris(2-aminoethylamine) conjugated three Phe-Phe dipeptides, produced (Phe-Phe)(3)TREN (7) resulted in spherical morphology structures interconnected by fibers. A rational design of two peptide conjugates, by introducing two different linker's, direct different self-assemble pathway, which result in distinct morphologies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.063
• 作为产物：
  描述：

  BOC-L-苯丙氨酸琥珀酰亚胺酯 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 2,5-吡咯烷二酮,1-[[N-[(1,1-二甲基乙氧基)羰基]-L-苯基丙氨酰-L-苯基丙氨酰]氧代]-
  参考文献：
  名称：

  邻苯二甲酰金刚烷-酪氨酸结合物的合成及光化学反应性

  摘要：

  摘要 合成了含有金刚烷基邻苯二甲酰亚胺和酪氨酸的二肽3，四肽4和五肽5，并对其光化学反应性进行了研究。激发到三重激发态时，3不会产生任何光产物，尽管光诱导的电子转移（PET）应基于热力学性质进行。四肽4和五肽5具有光化学反应性，在激发时会分解。酪氨酸和邻苯二甲酰亚胺之间的PET解释了预期的光脱羧反应性的缺乏。然而，产生苯氧基自由基的苯氧基自由基阳离子的去质子化或提供起始材料的反向电子转移的质子化可能比链内单电子转移更快，这将导致羧基自由基和脱羧。结果表明，通过正确选择反应物的氧化还原电位及其酸/碱性质，微调分子结构以获得所需的光反应性的重要性。 图形概要

  DOI：

  10.1007/s11164-017-2927-2

文献信息

• [EN] LEVORPHANOL PRODRUGS AND PROCESSES FOR MAKING AND USING THEM<br/>[FR] PROMÉDICAMENTS DE LEVORANOL ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：KEMPHARM INC

  公开号：WO2018191472A1

  公开（公告）日：2018-10-18

  The presently described technology provides compositions of one or more of oxoacids, polyethylene glycols, and vitamin compounds chemically conjugated to levorphanol ((-)-17-methylmorphinan-3-ol) to form novel prodrugs and compositions of levorphanol.

  目前描述的技术提供了一种或多种羟基酸、聚乙二醇和维生素化合物与左旋吗啡醇((-)-17-甲基吗啡-3-醇)在化学上结合形成新型前药和左旋吗啡的组合物。
• [EN] DEXTRORPHAN PRODRUGS AND PROCESSES FOR MAKING AND USING THEM<br/>[FR] PROMÉDICAMENTS DE DEXTRORPHANE ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：KEMPHARM INC

  公开号：WO2018191477A1

  公开（公告）日：2018-10-18

  The presently described technology provides compositions of one or more of oxoacids, polyethylene glycols, and/or vitamin compounds chemically conjugated to dextrorphan, (+)-17-methylmorphinan-3-ol), to form novel prodrugs and compositions of dextrorphan.

  目前描述的技术提供了将一种或多种羟基酸、聚乙二醇和/或维生素化学共轭到右旋丙啡醇（(+)-17-甲基吗啡酮-3-醇）上，形成新型前药和右旋丙啡醇组合物的配方。
• Photocyclization of Tetra- and Pentapeptides Containing Adamantylphthalimide and Phenylalanines: Reaction Efficiency and Diastereoselectivity
  作者：Margareta Sohora、Mario Vazdar、Irena Sović、Kata Mlinarić-Majerski、Nikola Basarić

  DOI：10.1021/acs.joc.8b01785

  日期：2018.12.21

  the linear peptides disclosed conformational reasons for the observed diastereoselectivity, being due to the peptide backbone spatial orientation imposed by the Phe amino acids. The photochemical efficiency for the decarboxylation and cyclization is not dependent on the peptide length, but it depends on the oxidation potential of the amino acid at the C-terminus. The results described herein are particularly

  合成了一系列四肽和五肽，其在N端带有邻苯二甲酰亚胺发色团。肽的C末端被氨基酸Phe，Phe（OMe）或Phe（OMe）2战略性地取代具有不同的氧化电位。通过制备性辐射和光产物的分离以及激光闪光光解研究了肽的光化学反应性。光激发后，这些肽会经历光诱导电子转移（PET）和脱羧作用，然后进行非对映选择性环化，保留四肽构型或五肽构型反转。分子动力学（MD）模拟和NOE实验支持分配环状肽的立体化学。线性肽的MD模拟公开了观察到的非对映选择性的构象原因，这是由于Phe氨基酸施加的肽主链空间取向。脱羧和环化的光化学效率不取决于肽的长度，而是取决于C末端氨基酸的氧化电位。本文所述的结果对于合理设计有效光化学反应以制备具有所需选择性的环肽特别重要。
• Synthesis and biological activity of peptide hydroxamate inhibitors of degradation of substance P analogues
  作者：A Ewenson、R Laufer、J Frey、M Chorev、Z Selinger、C Gilon

  DOI：10.1016/0223-5234(92)90001-h

  日期：1992.4

  A series of hydroxamic acid derivatives of peptides related to fragments of substance P (SP) were synthesized. Methyl, ethyl or N-hydroxy-succinimide ester precursors of the desired peptides were prepared by using classical peptide synthesis methodology and these were reacted with excess hydroxylamine in either ethanol or NN-dimethylformamide. The products were characterized by chromatographic methods, amino acid analysis and fast atom bombardment mass spectrometry. The inhibition of the degradation of the radiolabelled substrate desamino-[3-I-125-tyroSyl5]SP(5-11) ([(I-125)BH5]SP(5-11)) by these compounds in rat hypothalamus preparations was determined. The most potent inhibitors found were Boc-Phe-Phe-Phe-NHOH (12d, IC50 = 4-mu-M), Boc-Phe-Phe-Trp-NHOH (9, IC50 = 5-mu-M) and desamino-Tyr-Phe-Phe-Gly-NHOH (22, IC50 = 1.8-mu-M). A model describing the interaction of these compounds with the active site is proposed.
• Cyclic peptide-nucleotide hybrids (cPNH) with phosphoramidate bonds
  作者：Michael Morr、Anke Waßmann、Victor Wray

  DOI：10.1016/s0040-4020(99)00079-4

  日期：1999.3

  The potential of the generally applicable intramolecular condensation of 3'-N-aminoacyl/peptidyl-5'-nucleotides with the water soluble carbodiimide, 1-ethyl-3-(3-dimethyiaminopropyl)carbodiimide hydrochloride, for the production of cyclic peptide-nucleotide-hybrids has been extensively explored. (C) 1999 Elsevier Science Ltd. All rights reserved.