(2S)-2-(anthracene-9-carbonylamino)pentanedioic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (2S)-2-(anthracene-9-carbonylamino)pentanedioic acid
• 化学式: C₂₇H₂₇ClNO₄Pol
• 分子量: 351.4
• InChiKey: GCYNTDHVWWXPSS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-(anthracene-9-carbonylamino)pentanedioic acid 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 4.0h， 生成 N-(9-anthracenoyl)-L-aspartic acid
  参考文献：
  名称：

  Facile synthesis of anthracene-appended amino acids as highly selective and sensitive fluorescent Fe3+ ion sensors

  摘要：

  We designed new fluorescent chemical sensors for Fe3+ ion detection, by conjugating amino acids as receptors into an anthracene fluorophore. The conjugates were synthesized in solid phase by Fmoc-chemistry. Fluorescence sensors containing Asp (1) and Glu (2) both had exclusive selectivity for Fe3+ in 100% aqueous solution and in a mixed organic-aqueous solvent system. Other metal ions did not interfere with the detection ability of the sensors for Fe3+. The sensors detect Fe3+ ions via a chelation-enhanced fluorescent quenching effect. The binding affinity, reversible monitoring, and pH sensitivity of the sensors were investigated. In addition, detection of fluoride ion among halide ions was done by a chemosensing ensemble method with 1-Fe3+ and 2-Fe3+ complexes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.036
• 作为产物：
  描述：

  2-chlorotrityl chloride polystyrene resin 、 Fmoc-L-天冬氨酸 beta-叔丁酯 在 N,N-二异丙基乙胺 、 甲醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-(anthracene-9-carbonylamino)pentanedioic acid
  参考文献：
  名称：

  基于1,2-二硫杂环戊烷衍生物的高功能性DNA纳米颗粒的配制

  摘要：

  合成病毒的模型：基于离子相互作用和可聚合的1,2-二硫杂环戊烷，已生产出高度单分散且可功能化的DNA纳米颗粒。将准单分子DNA与含有聚合物诱导剂的阳离子去污剂浓缩。然后，非特异性阳离子颗粒也基于1,2-二硫杂环戊烷基序用阴离子聚乙二醇化缀合物进行功能化。

  DOI：

  10.1002/cbic.201402657

文献信息

• New 4-Aminoproline-Based Small Molecule Cyclopeptidomimetics as Potential Modulators of α4β1 Integrin
  作者：Andrea Sartori、Kelly Bugatti、Elisabetta Portioli、Monica Baiula、Irene Casamassima、Agostino Bruno、Francesca Bianchini、Claudio Curti、Franca Zanardi、Lucia Battistini

  DOI：10.3390/molecules26196066

  日期：——

  molecular modeling studies. The new compounds were synthesized through SPPS procedures followed by in-solution cyclization maneuvers. The biological evaluation of the new cyclic ligands in cell adhesion assays on Jurkat cells revealed promising submicromolar agonist activity in one compound, namely, the c[Amp(MPUPA)Val-Asp-Leu] cyclopeptide. Further investigations will be necessary to complete the characterization

  整合素 α 4 β 1属于白细胞整合素家族，鉴于其在介导炎症、自身免疫病理和癌症相关疾病中的主要作用，它代表了相关的治疗靶点。目前工作的重点是设计、合成和表征新的拟肽化合物，这些化合物可能能够识别 α 4 β 1整联蛋白并干扰其功能。为此，收集了七种新的环状肽模拟物，它们都具有嫁接到关键 α 4 β 1上的 4-氨基脯氨酸 (Amp) 核心支架在分子建模研究的支持下，设计了识别序列和（2-甲基苯基）脲基-苯乙酰（MPUPA）附属物。新化合物是通过 SPPS 程序合成的，然后是溶液中的环化操作。在 Jurkat 细胞的细胞粘附测定中对新环状配体的生物学评估揭示了一种化合物，即c [Amp(MPUPA)Val-Asp-Leu] 环肽具有良好的亚微摩尔激动剂活性。需要进一步研究以完成此类化合物的表征。
• Structure-activity relationship of marinostatin, a serine protease inhibitor isolated from a marine organism
  作者：Misako Taichi、Tohimasa Yamazaki、Kazuki Kawahara、Daisuke Motooka、Shota Nakamura、Shusaku Harada、Tadashi Teshima、Tadayasu Ohkubo、Yuji Kobayashi、Yuji Nishiuchi

  DOI：10.1002/psc.1244

  日期：2010.7

  A 12‐residue MST isolated from a marine organism is a potent serine protease inhibitor that has a double cyclic structure composed of two ester linkages formed between the β‐hydroxyl and β‐carboxyl groups, Thr3‐Asp9 and Ser8‐Asp11. MST was synthesized by a regioselective esterification procedure employing two sets of orthogonally removable side‐chain protecting groups for the Asp and Ser/Thr residues

  从海洋生物中分离出的12个残基的MST是一种有效的丝氨酸蛋白酶抑制剂，具有双环结构，该结构由在β-羟基和β-羧基之间的两个酯键Thr 3- Asp 9和Ser 8- Asp 11组成。。MST是通过区域选择性酯化方法合成的，该方法使用了针对Asp和Ser / Thr残基的两组正交可去除的侧链保护基。在MST分子中，通过改变酯化顺序，收率没有明显变化。MST的SAR研究表明，表达抑制活性的最低要求结构是单环结构中的序列（1–9），其中Pro 7位于环中的轴承在保持结构刚度方面起着至关重要的作用。通过应用MST的结构基序，我们合理地设计了不同于天然产物的蛋白酶抑制特异性。版权所有©2010欧洲肽协会和John Wiley＆Sons，Ltd.。
• Introduction of Pro and Its Analogues in the Conserved P1 Position of Trypsin Inhibitor SFTI-1 Retains Its Inhibitory Activity
  作者：Anna Legowska、Dawid Debowski、Rafal Lukajtis、Emilia Sztabkowska、Aneta Mizeria、Krzysztof Brzozowski、Magdalena Wysocka、Adam Lesner、Krzysztof Rolka

  DOI：10.2174/092986611797201002

  日期：2011.11.1

  A number of monocyclic SFTI-1 analogues modified in the conserved inhibitor P1 position by Pro, its L-hydroxyproline (Hyp) derivative as well as mimetics with different ring size were synthesized by the solid-phase method. Replacement of Ser6 by Pro, Hyp, and a four-member ring, L-azetidine-2-carboxylic acid (Aze), retained trypsin or chymotrypsin inhibitory activity. The determined association equilibrium constants of these analogues with a cognate enzyme were about two orders of magnitude lower than those obtained for ones with conserved Ser6. In all analogues, with the exception of one, [Phe5,Aze6]SFTI-1, the P1-P1 reactive site remained intact. The results provide first evidence that the conserved Ser in the P1 position of Bowman-Birk inhibitors can be successfully replaced by an amino acid with a secondary amine group.

  通过固相法合成了许多单环SFTI-1类似物，在保守的抑制剂P1位上分别用脯氨酸、其L-羟脯氨酸（Hyp）衍生物以及具有不同环大小的模拟物进行了修饰。用脯氨酸、Hyp和四元环L-氮杂环丁烷-2-羧酸（Aze）取代Ser6保留了胰蛋白酶或糜蛋白酶的抑制活性。这些类似物与同源酶的确定的结合平衡常数比保守的Ser6的常数低两个数量级。在所有类似物中，除了一种[Phe5,Aze6]SFTI-1外，P1-P1反应位点保持不变。这些结果首次证明，鲍曼-比尔克抑制剂P1位上保守的Ser可以成功地被具有仲胺基团的氨基酸取代。
• PD-L1/STING conjugates and methods of use
  申请人：Incyte Corporation

  公开号：US11596692B1

  公开（公告）日：2023-03-07

  The present application relates to conjugates of STING agonists and small molecule modulators of the PD-1/PD-L1 protein/protein interaction, as well as methods of treating cancer using the conjugates.
• Formulation of Highly Functionalizable DNA Nanoparticles Based on 1,2-Dithiolane Derivatives
  作者：Coralie Charrat、Anaïs Biscotti、Guilhem Godeau、Jacques Greiner、Pierre Vierling、Jean-Marie Guigonis、Christophe Di Giorgio

  DOI：10.1002/cbic.201402657

  日期：2015.3.23

  Model of synthetic viruses: Highly monodisperse and functionalizable DNA nanoparticles based on ionic interactions and polymerizerable 1,2‐dithiolane have been produced. Quasi‐monomolecular DNA was condensed with cationic detergents containing the polymeric inducer. Then, the nonspecific cationic particles were functionalized with anionic PEGylated conjugates, also based on 1,2‐dithiolane motifs.

  合成病毒的模型：基于离子相互作用和可聚合的1,2-二硫杂环戊烷，已生产出高度单分散且可功能化的DNA纳米颗粒。将准单分子DNA与含有聚合物诱导剂的阳离子去污剂浓缩。然后，非特异性阳离子颗粒也基于1,2-二硫杂环戊烷基序用阴离子聚乙二醇化缀合物进行功能化。