ethyl (2S)-2-(hexadecanoylamino)-3-(1H-indol-3-yl)propanoate | 261734-91-2

• 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: ethyl (2S)-2-(hexadecanoylamino)-3-(1H-indol-3-yl)propanoate
• CAS: 261734-91-2
• 化学式: C₂₉H₄₆N₂O₃
• 分子量: 470.696
• InChiKey: ALVCOKRHOMNKCT-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2S)-2-(hexadecanoylamino)-3-(1H-indol-3-yl)propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N-palmitoyl-L-tryptophan
  参考文献：
  名称：

  基于肽的软结构中溶剂介导的形态学转化

  摘要：

  自组装通常用于设计和制造新的和先进的材料。诸如短肽之类的生物构件进行自组装，以揭示各种分层结构，例如纳米管，纤维和球形结构。基于肽的软球形结构潜在地可用于多种应用，包括用于药物递送的载体和生物分子。该报告描述了一种三棕榈酸酯化的三氟甲磺酸二色氨酸肽缀合物（5），当使用较高浓度的二氯甲烷时，其会自组装形成空心球以及表面上的孔，但是在甲苯溶剂中加热时会形成纤维结构。

  DOI：

  10.1016/j.tet.2008.05.003
• 作为产物：
  描述：

  L-色氨酸乙酯盐酸盐 、 棕榈酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以1.5 g的产率得到ethyl (2S)-2-(hexadecanoylamino)-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  基于肽的软结构中溶剂介导的形态学转化

  摘要：

  自组装通常用于设计和制造新的和先进的材料。诸如短肽之类的生物构件进行自组装，以揭示各种分层结构，例如纳米管，纤维和球形结构。基于肽的软球形结构潜在地可用于多种应用，包括用于药物递送的载体和生物分子。该报告描述了一种三棕榈酸酯化的三氟甲磺酸二色氨酸肽缀合物（5），当使用较高浓度的二氯甲烷时，其会自组装形成空心球以及表面上的孔，但是在甲苯溶剂中加热时会形成纤维结构。

  DOI：

  10.1016/j.tet.2008.05.003

文献信息

• Membrane protein oxidation determines neuronal degeneration
  作者：Parvana Hajieva、Nadhim Bayatti、Matthias Granold、Christian Behl、Bernd Moosmann

  DOI：10.1111/jnc.12987

  日期：2015.5

  AbstractOxidative stress is an early hallmark in neurodegenerative disorders such as Alzheimer's and Parkinson's diseases. However, the critical biochemical effector mechanisms of oxidative neurotoxicity have remained surprisingly elusive. In screening various peroxides and potential substrates of oxidation for their effect on neuronal survival, we observed that intramembrane compounds were significantly more active than aqueous or amphiphilic compounds. To better understand this result, we synthesized a series of competitive and site‐specific membrane protein oxidation inhibitors termed aminoacyllipids, whose structures were designed on the basis of amino acids frequently found at the protein‐lipid interface of synaptic membrane proteins. Investigating the aminoacyllipids in primary neuronal culture, we found that the targeted protection of transmembrane tyrosine and tryptophan residues was sufficient to prevent neurotoxicity evoked by hydroperoxides, kainic acid, glutathione‐depleting drugs, and certain amyloidogenic peptides, but ineffective against non‐oxidative inducers of apoptosis such as sphingosine or Akt kinase inhibitors. Thus, the oxidative component of different neurotoxins appears to converge on neuronal membrane proteins, irrespective of the primary mechanism of cellular oxidant generation. Our results indicate the existence of a one‐electron redox cycle based on membrane protein aromatic surface amino acids, whose disturbance or overload leads to excessive membrane protein oxidation and neuronal death. image Membrane proteins have rarely been investigated as potential victims of oxidative stress in the context of neurodegeneration. This study provides evidence that excessive one‐electron oxidation of membrane proteins from within the lipid bilayer, depicted in the graphic, is a functionally decisive step toward neuronal cell death in response to different toxins.
• TRYPTOPHANYLESTER UND DEREN N-ACYL-DERIVATE ZUR PRÄVENTION UND THERAPIE VON ERKRANKUNGEN, DIE DURCH OXIDATIONSPROZESSE VERURSACHT ODER VERSTÄRKT WERDEN
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP1113795B1

  公开（公告）日：2005-07-13
• Tryptophanyl-esters and their N-acyl derivatives for preventing and treating diseases caused or aggravated by oxidation processes
  申请人：——

  公开号：US20040176436A1

  公开（公告）日：2004-09-09

  Use of a tryptophanyl-ester or an N-acyl derivative of a tryptophanyl-ester for the prophylaxis and therapy of oxidative pathologic processes in degenerative diseases and/or cancer diseases. Thereby, the tryptophanyl-ester or its N-acyl derivative is preferred to be tryptophanoctyl, N-oleoyl-tryptophanethyl-ester or N-dodecanoyl-tryptophanethyl-ester. Furthermore the tryptophanyl-esters and their N-acyl derivatives are preferred to be used for the treatment and/or prophylaxis of neurodegenerative diseases, cataracts, neoplastic diseases and/or cardiovascular diseases. In particular, the invention relates to the use of the tryptophanyl-esters and their N-acyl derivatives for the treatment and/or prophylaxis of Alzheimer's disease, Parkinson's disease, apoplectic fit, amyotrophic lateral sclerosis, cancers, arteriosclerosis and/or myocardial infarction. In addition, the invention relates to a pharmaceutical composition comprising a tryptophanyl-ester or an N-acyl derivative of a tryptophanyl-ester.
• [DE] TRYPTOPHANYLESTER UND DEREN N-ACYL-DERIVATE ZUR PRÄVENTION UND THERAPIE VON ERKRANKUNGEN, DIE DURCH OXIDATIONSPROZESSE VERURSACHT ODER VERSTÄRKT WERDEN<br/>[EN] TRYPTOPHANYL ESTER AND THEIR N-ACYL DERIVATIVES FOR THE PREVENTION AND TREATMENT OF DISEASES CAUSED OR EXACERBATED BY OXIDATION PROCESSES<br/>[FR] ESTERS DE TRYPTOPHANYLE ET LEURS DERIVES N-ACYLE DESTINES A LA PREVENTION ET AU TRAITEMENT DE MALADIES DUES AU PROCEDE D'OXYDATION OU AMPLIFIEES PAR CE DERNIER
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2000015206A2

  公开（公告）日：2000-03-23

  Verwendung eines Tryptophanylesters oder eines N-Acyl-Derivates eines Tryptophanylesters zur Prophylaxe und Therapie von oxidativen pathologischen Prozessen bei degenerativen Erkrankungen und/oder Krebserkrankungen. Dabei ist bevorzugt, daß der Tryptophanylester oder dessen N-Acyl-Derivat Tryptophanoctylester, N-Oleoyl-tryptophanethylester, oder N-Dodecanoyl-tryptophanethylester ist. Ferner ist bevorzugt, daß die Tryptophanylester und deren N-Acyl-Derivate zur Behandlung und/oder Prophylaxe von neurodegenerativen Erkrankungen, Katarakten, neoplastischen Erkrankungen und/oder Herz-Kreislauferkrankungen verwendet werden. Insbesondere betrifft die Erfindung die Verwendung der Tryptophanylester und deren N-Acyl-Derivate zur Behandlung und/oder Prophylaxe von Morbus Alzheimer, Morbus Parkinson, Schlaganfall, Amyotrophe Lateralsklerose, Krebsen, Arteriosklerose und/oder Herzinfarkt. Darüber hinaus betrifft die Erfindung ein Arzneimittel, das einen Tryptophanylester oder ein N-Acyl-Derivat eines Tryptophanylesters umfasst.
• Solvent-mediated morphological transformations in peptide-based soft structures
  作者：Surajit Ghosh、Sandeep Verma

  DOI：10.1016/j.tet.2008.05.003

  日期：2008.6

  fabrication of new and advanced materials. Biological building blocks such as short peptides undergo self-assembly to reveal a variety of hierarchical structures such as nanotubes, fibers, and spherical structures. Peptide-based soft spherical structures are potentially useful for a variety of applications including vehicles for drug delivery and biological molecules. This report describes a tripalmitoylated

  自组装通常用于设计和制造新的和先进的材料。诸如短肽之类的生物构件进行自组装，以揭示各种分层结构，例如纳米管，纤维和球形结构。基于肽的软球形结构潜在地可用于多种应用，包括用于药物递送的载体和生物分子。该报告描述了一种三棕榈酸酯化的三氟甲磺酸二色氨酸肽缀合物（5），当使用较高浓度的二氯甲烷时，其会自组装形成空心球以及表面上的孔，但是在甲苯溶剂中加热时会形成纤维结构。