(2R)-2-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)氧基]-4-甲基-戊酸 | 310404-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: (2R)-2-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)氧基]-4-甲基-戊酸
• 英文名称: D-Phth^N-OLeu
• 英文别名: (R)-4-methyl-2-phthalimidooxypentanoic acid；D-PhthN-O-Leu-OH；(R)-2-(1,3-Dioxoisoindolin-2-yloxy)-4-methylpentanoic acid；(2R)-2-(1,3-dioxoisoindol-2-yl)oxy-4-methylpentanoic acid
• CAS: 310404-45-6
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: MDMVYIQIEZUFLJ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)氧基]-4-甲基-戊酸 在 1-羟基苯并三唑 、 一水合肼 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成
  参考文献：
  名称：

  A Reverse Turn Structure Induced by a d,l-α-Aminoxy Acid Dimer

  摘要：

  Our previous work revealed that two adjacent D-a-aminoxy acids could form two homochiral N-O turns, with the backbone folding into an extended helical structure (1.8(8)-helix). Here, we report the conformational studies of linear peptides 3-6, which contain a D,L-alpha-aminoxy acid dimer segment. The NMR and X-ray analysis of 3 showed that it folded into a loop conformation with two heterochiral N-O turns. This loop segment can be used to constrain tetrapeptides 4 and 6 to form a reverse turn structure. H-1 NMR dilution studies, DMSO-d(6) addition studies, and 2D-NOESY data indicated that tetrapeptides 4 and 6 folded into reverse turn conformations featured by a head-to-tail 16-membered-ring intramolecular hydrogen bond. In contrast, tetrapeptide 5 with L-Ala instead of Gly or D-Ala as the N-terminal amino acid could not form the desired reverse turn structure for steric reasons. Quantum mechanics calculations showed that model pentamide 7, with the same substitution pattern of 4, adopted a novel reverse turn conformation featuring two heterochiral N-O turns (each of an 8-membered ring hydrogen bond), a cross-strand 16-membered ring hydrogen bond, and a 7-membered ring gamma-turn.

  DOI：

  10.1021/ja029514j
• 作为产物：
  描述：

  benzyl (R)-4-methyl-2-phthalimidooxypentanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以79%的产率得到(2R)-2-[(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)氧基]-4-甲基-戊酸
  参考文献：
  名称：

  由L-氨基酸或L-羟基酸合成光学活性的邻苯二甲酰基D-氨基氧基酸，作为制备氨基氧基肽的基础。

  摘要：

  DOI：

  10.1021/jo0006573

文献信息

• [EN] AMINOXY ACID-BASED ANTI-CANCER STEM CELL COMPOUNDS AND METHODS THEREOF<br/>[FR] COMPOSÉS DE CELLULES SOUCHES ANTI-CANCER À BASE D'ACIDE AMINOXY ET PROCÉDÉS ASSOCIÉS
  申请人：UNIV HONG KONG

  公开号：WO2021104199A1

  公开（公告）日：2021-06-03

  Provided are synthetic small molecules and their use as drug, in particular in the treatment of cancer. Also provided is a method of inhibiting cancer stem cells. Also provided is a method for treatment of cancers and other diseases by affecting mitochondrial functions. Also provided is a method of making and using of the compounds.

  提供了合成小分子及其作为药物的用途，特别是在癌症治疗中的应用。还提供了一种抑制癌症干细胞的方法。还提供了一种通过影响线粒体功能治疗癌症和其他疾病的方法。还提供了一种制备和使用这些化合物的方法。
• Chiral α-Aminoxy Acid/Achiral Cyclopropane α-Aminoxy Acid Unit as a Building Block for Constructing the α N−O Helix
  作者：Dan Yang、Xiao-Wei Chang、Dan-Wei Zhang、Ze-Feng Jiang、Ke-Sheng Song、Yu-Hui Zhang、Nian-Yong Zhu、Lin-Hong Weng、Min-Qin Chen

  DOI：10.1021/jo100810m

  日期：2010.7.16

  revealed that the biased handedness of α N−O turn found in OAcc residue depends on its preceding chiral residue. It was then found that the helical conformation was destroyed in the case of oligopeptides 6 and 7 [OAA-(OAcc)n, n = 2, 3]. The crystal structure of tripeptide 8 (iPrCO-d-OVal-OAcc-d-OVal-NHiBu) further disclosed the helical structure formed by three consecutive homochiral α N−O turns. This study

  单体1从非手性的1-（氨氧基）环丙烷羧酸（OACC）和寡肽衍生的2 - 9由手性α氨氧基酸的和如OACC非手性α氨氧基酸的合成和它们的结构特征。八元环分子内氢键，即αN-O圈，在相邻残基之间形成，与它们的手性无关。但是，螺旋的形成是序列依赖性的。在N末端带有手性α-氨基酸（d -OAA）的二肽2和在C末端具有非手性OAcc的二肽优先采用右旋1.8 8螺旋结构，但是二肽3（OAcc- d-OAA）没有。理论计算结果与实验结果吻合良好，表明在OAcc残基中发现的αN-O转弯的偏向性取决于其先前的手性残基。然后发现在寡肽6和7 [OAA-（OAcc）n，n＝ 2，3]的情况下，螺旋构象被破坏。三肽8（i PrCO- d -OVal-OAcc - d -OVal-NH i的晶体结构Bu）进一步公开了由三个连续的同手性αN-O匝形成的螺旋结构。这项研究发现了非手性氨基氧酸残基（如OAcc单元）是一种
• Disulfide Bond Creates a Small Connecting Loop in Aminoxy Peptide Backbone
  作者：Dan Yang、Guo-Jun Liu、Zhi-Gang Jiao、Dan-Wei Zhang、Zheng Luo、Ke-Sheng Song、Min-Qin Chen

  DOI：10.1002/chem.200800095

  日期：2008.11.17

  cysteine-cysteine pairs is often critical to the folding behavior, stability, and functionality of proteins. In this paper, we report that sulfur atoms can be introduced into the amide groups of aminoxy peptides to form a novel type of disulfide bridge, which creates a connecting loop in the peptide backbone.

  半胱氨酸-半胱氨酸对的侧链之间的二硫键形成通常对蛋白质的折叠行为，稳定性和功能至关重要。在本文中，我们报道了可以将硫原子引入到氨氧基肽的酰胺基团中以形成新型的二硫键，从而在肽主链上形成一个连接环。
• Method of Modulating Membrane Potential of a Cell
  申请人：Yang Dan

  公开号：US20090163595A1

  公开（公告）日：2009-06-25

  Provided herein are methods of modulating membrane potential of a cell membrane using self-assembling compounds. Also provided herein are methods of regulating a natural voltage-dependent ion channel in a cell membrane using the self-assembling compounds disclosed herein. Further provided herein are methods of treating, preventing and/or managing a disease that is related to the abnormal membrane potential responses by using the self-assembling compounds disclosed herein.

  本文提供了使用自组装化合物调节细胞膜的膜电位的方法。本文还提供了使用所披露的自组装化合物调节细胞膜中自然电压依赖离子通道的方法。此外，本文还提供了使用所披露的自组装化合物治疗、预防和/或管理与异常膜电位反应相关的疾病的方法。
• Synthetic Ion Channels
  申请人：Yang Dan

  公开号：US20080146513A1

  公开（公告）日：2008-06-19

  Provided herein are self-assembling compounds that can form ion channels in lipid bilayers or cell membranes and ion-channel-forming compositions comprising the self-assembling compounds. Also provided are methods of making and using the ion channels formed from a plurality of molecules of the self-assembling compounds. Further, provided are methods of treating or preventing conditions and diseases that are related to the dysfunction of ion channels, including chloride channels.

  本文提供了能够在脂质双分子层或细胞膜中形成离子通道的自组装化合物，以及包含这些自组装化合物的离子通道形成组合物。还提供了利用由多种分子自组装化合物形成的离子通道的制备和使用方法。此外，还提供了治疗或预防与离子通道功能失调相关的疾病和情况的方法，包括氯离子通道。