(S)-3-(3-acetylphenyl)-2-aminopropanoic acid | 474519-58-9

• 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: (S)-3-(3-acetylphenyl)-2-aminopropanoic acid
• 英文别名: m-Acetylphenylalanine；(2S)-3-(3-acetylphenyl)-2-aminopropanoic acid
• CAS: 474519-58-9
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: IBCKYXVMEMSMQM-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-(3-acetylphenyl)-2-aminopropanoic acid 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Fmoc-m-acetyl-L-phenylalanine
  参考文献：
  名称：

  Iminoboronate-Based Peptide Cyclization That Responds to pH, Oxidation, and Small Molecule Modulators

  摘要：

  As a rich source of therapeutic agents, peptide natural products usually adopt a cyclic or multicyclic scaffold that minimizes structural flexibility to favor target binding. Inspired by nature, chemists have been interested in developing synthetic cyclic and multicyclic peptides that serve as biological probes and potential therapeutics. Herein we describe a novel strategy for peptide cyclization in which intramolecular iminoboronate formation allows spontaneous cyclization under physiologic conditions to yield monocyclic and bicyclic peptides. Importantly the iminoboronate-based cyclization can be rapidly reversed in response to multiple stimuli, including pH, oxidation, and small molecules. This highly versatile strategy for peptide cyclization should find applications in many areas of chemical biology.

  DOI：

  10.1021/jacs.5b12301
• 作为产物：
  描述：

  2-氨基-3-(3-乙酰基-4-羟基苯基)丙酸 在 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 20.75h， 生成 (S)-3-(3-acetylphenyl)-2-aminopropanoic acid
  参考文献：
  名称：

  Iminoboronate-Based Peptide Cyclization That Responds to pH, Oxidation, and Small Molecule Modulators

  摘要：

  As a rich source of therapeutic agents, peptide natural products usually adopt a cyclic or multicyclic scaffold that minimizes structural flexibility to favor target binding. Inspired by nature, chemists have been interested in developing synthetic cyclic and multicyclic peptides that serve as biological probes and potential therapeutics. Herein we describe a novel strategy for peptide cyclization in which intramolecular iminoboronate formation allows spontaneous cyclization under physiologic conditions to yield monocyclic and bicyclic peptides. Importantly the iminoboronate-based cyclization can be rapidly reversed in response to multiple stimuli, including pH, oxidation, and small molecules. This highly versatile strategy for peptide cyclization should find applications in many areas of chemical biology.

  DOI：

  10.1021/jacs.5b12301

文献信息

• [EN] MULTIFUNCTIONAL MEMBRANE-ACTIVE AMINOGLYCOSIDE-PEPTIDE CONJUGATES<br/>[FR] CONJUGUÉS AMINOGLYCOSIDE-PEPTIDE MULTIFONCTIONNELS À ACTIVITÉ MEMBRANAIRE
  申请人：UNIV CALIFORNIA

  公开号：WO2016025627A1

  公开（公告）日：2016-02-18

  Compositions and methods are disclosed that relate to aminoglycoside-linker-peptide (P-L-A) conjugates having unexpectedly advantageous dual-function bactericidal properties. Encompassed compounds are shown to be capable of energy independent bacterial plasma membrane disruption and to exhibit potent toxicity to bacteria including antibiotic-resistant bacteria. These and related embodiments will find uses for treating bacterial infections including overcoming antibiotic resistance.

  揭示了与氨基糖苷-连接肽（P-L-A）共轭物相关的具有意外优势双重杀菌性能的组合物和方法。所涵盖的化合物被证明能够独立于能量的细菌质膜破坏，并对包括抗生素耐药细菌在内的细菌表现出强大的毒性。这些及相关实施例将用于治疗细菌感染，包括克服抗生素耐药性。
• [EN] ANTIBODY-DRUG CONJUGATES<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT
  申请人：PFIZER

  公开号：WO2013068874A1

  公开（公告）日：2013-05-16

  Disclosed are anti-5T4 antibody drug conjugates with an improved pharmacokinetic profile and methods for preparing and using the same. In one embodiment, the antibody-drug conjugate has the formula Ab-(D)p, wherein Ab is an anti-5T4 antibody comprising a non- natural amino acid; D is a dolastatin linker derivative; and p is from about 1 to about 8.

  公开了具有改善的药代动力学特性的抗-5T4抗体药物偶联物，以及制备和使用相同的方法。在一个实施例中，抗体-药物偶联物具有公式Ab-(D)p，其中Ab是包含非天然氨基酸的抗-5T4抗体；D是dolastatin连接剂的衍生物；p是大约1到大约8。
• LIVER X RECEPTOR AGONISTS AND USES THEREOF
  申请人：The California Institute for Biomedical Research

  公开号：US20160324981A1

  公开（公告）日：2016-11-10

  Disclosed herein are antibody drug conjugates having an antibody or antibody fragment that binds a cell surface molecule on a target cell, wherein the target cell is a lymphocyte and a therapeutic agent that has a therapeutic effect in a subject in need thereof. Further disclosed herein are antibody drug conjugates having an antibody or antibody fragment that binds a cell surface molecule on a target cell; and a therapeutic agent that binds an intracellular moiety of the target cell. These antibody drug conjugates may be used for treating cardiovascular diseases.

  本文披露了一种抗体药物结合物，其具有结合靶细胞表面分子的抗体或抗体片段，其中所述靶细胞是淋巴细胞，并且具有对需要治疗的受体产生治疗效果的治疗剂。本文还披露了一种抗体药物结合物，其具有结合靶细胞表面分子的抗体或抗体片段；以及结合靶细胞的细胞内部分子的治疗剂。这些抗体药物结合物可用于治疗心血管疾病。
• Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1)
  作者：Huan-Chieh Chien、Claire Colas、Karissa Finke、Seth Springer、Laura Stoner、Arik A. Zur、Brooklynn Venteicher、Jerome Campbell、Colton Hall、Andrew Flint、Evan Augustyn、Christopher Hernandez、Nathan Heeren、Logan Hansen、Abby Anthony、Justine Bauer、Dimitrios Fotiadis、Avner Schlessinger、Kathleen M. Giacomini、Allen A. Thomas

  DOI：10.1021/acs.jmedchem.8b01007

  日期：2018.8.23

  Furthermore, we evaluated the structure–activity relationship (SAR) for both enantiomers of naturally occurring LAT1 substrates. Analogues were tested in cis-inhibition and trans-stimulation cell assays to determine potency and uptake rate. Surprisingly, LAT1 can transport amino acid-like substrates with wide-ranging polarities including those containing ionizable substituents. Additionally, the rate of LAT1

  L型氨基酸转运蛋白1（LAT1，SLC7A5）将必需氨基酸转运穿过血脑屏障（BBB）进入癌细胞。为了利用LAT1进行药物递送，需要有效的氨基酸基团，因为前药必须与毫摩尔浓度的内源氨基酸竞争。为了更好地理解可以提高效能的配体-转运体相互作用，我们开发了结构性LAT1模型来指导苯丙氨酸和组氨酸取代类似物的设计。此外，我们评估了天然存在的LAT1底物的两种对映异构体的结构活性关系（SAR）。测试了类似物的顺式抑制和反式-刺激细胞试验以确定效力和摄取率。出乎意料的是，LAT1可以运输极性较宽的氨基酸样底物，包括那些含有可电离取代基的底物。另外，即使对映异构体可能表现出不同的结合模式，LAT1转运的速率通常也是非立体选择性的。我们的发现对脑部疾病和癌症的新治疗方法的开发具有广泛的意义。
• REAGENTS AND METHODS FOR REPLICATION, TRANSCRIPTION, AND TRANSLATION IN SEMI-SYNTHETIC ORGANISMS
  申请人：The Scripps Research Institute

  公开号：US20200392550A1

  公开（公告）日：2020-12-17

  Disclosed herein are compositions, methods, cells, engineered microorganisms, and kits for increasing the production of proteins or polypeptides comprising one or more unnatural amino acids. Further provided are compositions, cells, engineered microorganisms, and kits for increasing the retention of unnatural nucleic acids encoding the unnatural amino acids in an engineered cell, or semi-synthetic organism.

  本文揭示了一种用于增加含有一个或多个非天然氨基酸的蛋白质或多肽的生产的组合物、方法、细胞、工程微生物和试剂盒。此外，还提供了一种用于增加编码非天然氨基酸的非天然核酸在工程细胞或半合成生物体中的保留的组合物、细胞、工程微生物和试剂盒。