N-oleoyl-L-tryptophan | 149755-28-2

• 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: N-oleoyl-L-tryptophan
• 英文别名: N-oleoyl tryptophan；(2S)-3-(1H-indol-3-yl)-2-[[(Z)-octadec-9-enoyl]amino]propanoic acid
• CAS: 149755-28-2
• 化学式: C₂₉H₄₄N₂O₃
• 分子量: 468.68
• InChiKey: XAKJNQLDKZLAKM-ZDQMOETHSA-N

物化性质

• 沸点：
  688.4±55.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-oleoyl-L-tryptophan ethyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以78%的产率得到N-oleoyl-L-tryptophan
  参考文献：
  名称：

  Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials

  摘要：

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.

  DOI：

  10.1021/jo301659c

文献信息

• Discovery of Hydrolysis-Resistant Isoindoline <i>N</i>-Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
  作者：Hua Lin、Jonathan Z. Long、Alexander M. Roche、Katrin J. Svensson、Florence Y. Dou、Mi Ra Chang、Timothy Strutzenberg、Claudia Ruiz、Michael D. Cameron、Scott J. Novick、Charles A. Berdan、Sharon M. Louie、Daniel K. Nomura、Bruce M. Spiegelman、Patrick R. Griffin、Theodore M. Kamenecka

  DOI：10.1021/acs.jmedchem.8b00029

  日期：2018.4.12

  to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required

  N-酰基氨基酸直接结合线粒体并充当不依赖于 UCP1 的呼吸的内源解偶联剂。我们发现给小鼠施用N-酰基氨基酸可以改善葡萄糖稳态并增加能量消耗，表明该途径可能有助于治疗肥胖和相关疾病。我们报告了脂化N-酰基氨基酸及其非天然类似物的合成和线粒体解偶联生物活性的完整说明。中等长度的不饱和脂肪酸链和中性氨基酸头基是哺乳动物细胞上最佳解偶联活性所必需的。一类非天然N-酰基氨基酸类似物，其特征为异吲哚啉-1-羧酸酯头基（37），能够抵抗 PM20D1 的酶促降解，并在细胞和小鼠体内保持解偶联生物活性。
• <i>N</i>-Carboxyanhydride-Mediated Fatty Acylation of Amino Acids and Peptides for Functionalization of Protocell Membranes
  作者：Enver Cagri Izgu、Anders Björkbom、Neha P. Kamat、Victor S. Lelyveld、Weicheng Zhang、Tony Z. Jia、Jack W. Szostak

  DOI：10.1021/jacs.6b08801

  日期：2016.12.28

  sulfide has been shown to generate short peptides via the formation of cyclic amino acid N-carboxyanhydrides (NCAs). Here, we show that the polymerization of valine-NCA in the presence of fatty acids yields acylated amino acids and peptides via a mixed anhydride intermediate. Notably, Nα-oleoylarginine, a product of the reaction between arginine and oleic acid in the presence of valine-NCA, partitions

  早期的原始细胞很可能是由 RNA、肽和脂质分子的自组装产生的，这些分子在地球早期的地质有利环境中生成和集中。这些成分在提供化学能源的益生元环境中的反应性可能会产生具有有利于原始细胞出现的特性的其他物种。羰基硫对氨基酸的地球化学上合理的活化已被证明通过形成环状氨基酸 N-羧酸酐 (NCA) 产生短肽。在这里，我们表明缬氨酸-NCA 在脂肪酸存在下的聚合通过混合酸酐中间体产生酰化氨基酸和肽。值得注意的是，Nα-油酰精氨酸，在缬氨酸-NCA 存在下，精氨酸和油酸反应的产物，自发地进入囊泡膜并介导 RNA 与囊泡的结合。我们的结果表明了一种潜在的机制，通过该机制，活化的氨基酸可以使脂肪酸膜的化学功能多样化，并在早期原始细胞的形成过程中将 RNA 与囊泡共定位。
• CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US20200317613A1

  公开（公告）日：2020-10-08

  Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).

  解耦呼吸是一个众所周知的过程，可以增加细胞的呼吸和产热。本文提供了化学解耦剂，这些解耦剂是化合物(I)的化合物。还提供了使用化合物(I)预防或治疗代谢性疾病和调节代谢过程的方法。
• In Situ Synthesis of Gold and Silver Nanoparticles by Using Redox-Active Amphiphiles and Their Phase Transfer to Organic Solvents
  作者：Satyabrata Si、Enakshi Dinda、Tarun K. Mandal

  DOI：10.1002/chem.200701014

  日期：——

  An in situ reduction approach to synthesizing gold and silver nanoparticles by using a series of newly designed, redox-active amphiphiles at basic pH is described. These amphiphiles are the conjugates of a fatty acid (e.g., oleic acid, stearic acid, and lauric acid) and a redox-active amino acid (e.g., tryptophan or tyrosine). The amphiphile-coated nanoparticles are then efficiently transferred from

  描述了一种通过在碱性pH下使用一系列新设计的氧化还原活性两亲物来原位合成金和银纳米粒子的方法。这些两亲物是脂肪酸（例如油酸，硬脂酸和月桂酸）和氧化还原活性氨基酸（例如色氨酸或酪氨酸）的缀合物。然后，仅通过酸处理就可以将两亲涂层纳米颗粒从水中有效转移到不同的非极性有机介质（例如苯，甲苯，二甲苯，环己烷和己烷）中。通过紫外/可见光谱和透射电子显微镜监测相转移过程，结果表明，转移到有机介质后，平均粒径和粒径分布几乎保持不变。通过FTIR光谱和热重分析证实了两亲物对纳米颗粒表面的锚定。提出了一种机制来描述原位形成的胶态金纳米粒子和银纳米粒子的稳定性以及它们向有机溶剂中的相转移。两亲物的存在增加了胶体金纳米颗粒共轭物在有机溶剂中的热稳定性。
• METHODS OF TREATING LIVER DISEASE
  申请人：The J. David Gladstone Institutes

  公开号：EP3025727A1

  公开（公告）日：2016-06-01

  The present invention provides methods of treating liver steatosis, liver fibrosis and hepatitis C virus (HCV) infection; methods described include methods of reducing the incidence of complications associated with HCV and cirrhosis of the liver; and methods of reducing viral load, or reducing the time to viral clearance, or reducing morbidity or mortality in the clinical outcomes, in patients suffering from HCV infection.

  本发明提供了治疗肝脏脂肪变性、肝纤维化和丙型肝炎病毒（HCV）感染的方法；所述方法包括降低HCV和肝硬化相关并发症发病率的方法；以及降低HCV感染患者病毒载量、或缩短病毒清除时间、或降低临床结果中发病率或死亡率的方法。