芴甲氧羰基双酚A基 | 117666-96-3

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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
• 中文名称: 芴甲氧羰基双酚A基
• 中文别名: FMOC-L-4-苯甲酰基苯丙氨酸；氨基酸-4-苯甲酰基-L-苯丙氨酸；芴甲氧羰基双酚A；Fmoc-L-4-苯甲酰基苯丙氨酸
• 英文名称: Fmoc-4-benzoyl-L-phenylalanine
• 英文别名: Fmoc-BpaOH；(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-benzoylphenyl)propanoic acid；(2S)-3-(4-benzoylphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 117666-96-3
• 化学式: C₃₁H₂₅NO₅
• 分子量: 491.543
• InChiKey: SYOBJKCXNRQOGA-NDEPHWFRSA-N

物化性质

• 沸点：
  729.0±60.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，未有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 海关编码：
  2924 29 70
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封，在2ºC至-8ºC下保存

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-bpa-oh
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Fmoc-bpa-oh
CAS number: 117666-96-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C31H25NO5
Molecular weight: 491.5

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

Fmoc Bpa OH是一种苯丙氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  芴甲氧羰基双酚A基 在 哌啶 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-amino-3-(4-benzoylphenyl)-N-(prop-2-yn-1-yl)propanamide
  参考文献：
  名称：

  用于谷胱甘肽 S-转移酶同工酶和位点特异性功能表征的基于活性的探针

  摘要：

  谷胱甘肽 S 转移酶 (GST) 包括一个多样化的 II 期药物代谢酶家族，其共同功能是将还原型谷胱甘肽 (GSH) 与内生物质和异生物质结合。尽管可以测量这些酶的聚合活性，但不可能对复杂生物样品中异生物质代谢的异构体特异性贡献。我们开发了两种基于活性的探针 (ABP)，它们可以表征哺乳动物组织中的活性 GST。GST 活性位点由 GSH 结合“G 位点”和底物结合“H 位点”组成。因此，我们开发了 (1) 基于 GSH 的光亲和探针 (GSTABP-G) 以靶向“G 位点”，以及 (2) 设计用于模拟底物分子并具有“H 位点”活性的 ABP (GSTABP-H) . GSTABP-G 具有光反应性部分，用于紫外线诱导的 GST 和 GSH 结合酶的共价结合。GSTABP-H 是一种基于已知机制的 GST 抑制剂的衍生物，它结合在活性位点内并抑制 GST 活性。在肝脏中使用一系列竞争实验对

  DOI：

  10.1021/jacs.7b07378
• 作为产物：
  描述：

  L-对苯甲酰基苯丙氨酸 生成 芴甲氧羰基双酚A基
  参考文献：
  名称：

  KAUER, JAMES C.

  摘要：

  DOI：

文献信息

• Selective Substrates and Activity-Based Probes for Imaging of the Human Constitutive 20S Proteasome in Cells and Blood Samples
  作者：Wioletta Rut、Marcin Poręba、Paulina Kasperkiewicz、Scott J. Snipas、Marcin Drąg

  DOI：10.1021/acs.jmedchem.8b00026

  日期：2018.6.28

  the HyCoSuL approach, we designed and synthesized novel and selective fluorogenic substrates for each of these three constitutive 20S proteasome activities and applied them to assess inhibition of proteasome subunits by MG-132 and a clinically used inhibitor bortezomib. Our results confirm the utility of designed substrates in biochemical assays. Furthermore, selective peptide sequences obtained in this

  蛋白酶体是维持蛋白质稳态的关键酶复合物。蛋白酶体功能紊乱导致包括癌症，自身免疫和神经退行性疾病在内的病理。因此，蛋白酶体构成药物开发的极好的分子靶标。在这里，我们使用HyCoSuL方法为这三个20S组成型蛋白酶体活性中的每一个设计和合成了新颖的选择性荧光底物，并将它们应用于评估MG-132和临床使用的硼替佐米对蛋白酶体亚基的抑制作用。我们的结果证实了设计的底物在生化分析中的实用性。此外，以此方式获得的选择性肽序列用于构建荧光团标记的基于活性的探针，然后用于同时检测HEK-293F细胞和红细胞裂解液中的每个20S组成型蛋白酶体亚基。总体而言，我们描述了一种简单而快速的方法，可用于测量全血样本中20S组成型蛋白酶体的活性，该方法可以早期诊断与异常上调的蛋白酶体活性有关的病理状态。
• Development of Low Molecular Weight HIV-1 Protease Dimerization Inhibitors
  作者：You Seok Hwang、Jean Chmielewski

  DOI：10.1021/jm049581j

  日期：2005.3.1

  The role of HIV protease in viral replication has made it a significant target for inhibition. The focus of our studies is to target the dimerization interface of HIV-1 protease because disruption of the dimer will inhibit enzymatic activity. The initial strategy began with cross-linked peptides derived from the interface of HIV protease. Herein we describe the design of a focused library of agents

  HIV蛋白酶在病毒复制中的作用使其成为重要的抑制靶标。我们研究的重点是针对HIV-1蛋白酶的二聚界面，因为二聚体的破坏会抑制酶的活性。最初的策略始于源自HIV蛋白酶界面的交联肽。在本文中，我们描述了基于HIV-1蛋白酶二聚化抑制作用的最小药效基团的试剂集中库的设计。
• Optimization of linear and cyclic peptide inhibitors of KEAP1-NRF2 protein-protein interaction
  作者：Stefania Colarusso、Daniele De Simone、Tommaso Frattarelli、Matteo Andreini、Mauro Cerretani、Antonino Missineo、Daniele Moretti、Sara Tambone、Georg Kempf、Martin Augustin、Stefan Steinbacher、Ignacio Munoz-Sanjuan、Larry Park、Vincenzo Summa、Licia Tomei、Alberto Bresciani、Celia Dominguez、Leticia Toledo-Sherman、Elisabetta Bianchi

  DOI：10.1016/j.bmc.2020.115738

  日期：2020.11

  Inhibition of KEAP1-NRF2 protein-protein interaction is considered a promising strategy to selectively and effectively activate NRF2, a transcription factor which is involved in several pathologies such as Huntington’s disease (HD). A library of linear peptides based on the NRF2-binding motifs was generated on the nonapeptide lead Ac-LDEETGEFL-NH2 spanning residues 76–84 of the Neh2 domain of NRF2

  抑制KEAP1-NRF2蛋白质-蛋白质相互作用被认为是有选择地和有效地激活NRF2的一种有前途的策略，NRF2是一种转录因子，涉及多种病理学，例如亨廷顿舞蹈病（HD）。在非肽铅Ac-LDEETGEFL-NH 2上生成了基于NRF2结合基序的线性肽库跨越NRF2 Neh2域的76-84位残基，目的是用非酸性氨基酸取代E78，E79和E82。基于结构的设计还旨在更深入地了解T80副口袋的功能和可及性。研究了使用不同种类的环肽以及与细胞穿透肽结合的提高细胞通透性的方法。这一见识将指导大环化合物，肽模拟物以及最重要的是中性小脑穿透分子的未来设计，以评估NRF2激活剂是否可用于HD。
• Oral hypoglycaemic agents
  申请人：——

  公开号：US20020132812A1

  公开（公告）日：2002-09-19

  Compounds of formula (I) which are optionally substituted 2-(&ohgr;,&ohgr;-diarylalkyl)-4,5-dihydro-1H-imidazoles and 2-(&ohgr;,&ohgr;-diarylalkyl)-1,4,5,6-tetrahydropyrimidines and salts thereof with inorganic and organic acids have interesting pharmacological properties. Thus, the compounds are useful in the treatment of type 2 diabetes.

  式(I)的化合物，它们是可选择取代的2-(&ohgr;，&ohgr;-二芳基烷基)-4,5-二氢-1H-咪唑和2-(&ohgr;，&ohgr;-二芳基烷基)-1,4,5,6-四氢嘧啶及其与无机和有机酸的盐具有有趣的药理特性。因此，这些化合物在治疗2型糖尿病方面是有用的。
• Chemical Probes Unravel an Antimicrobial Defense Response Triggered by Binding of the Human Opioid Dynorphin to a Bacterial Sensor Kinase
  作者：Megan H. Wright、Christian Fetzer、Stephan A. Sieber

  DOI：10.1021/jacs.7b01072

  日期：2017.5.3

  stress, levels of the human opioid peptide dynorphin are elevated, triggering virulence in the opportunistic pathogenic bacterium Pseudomonas aeruginosa via an unknown pathway. Here we apply a multilayered chemical biology strategy to unravel the mode of action of this putative interkingdom signal. We designed and applied dynorphin-inspired photoaffinity probes to reveal the protein targets of the peptide

  通过小分子信号进行宿主-微生物交流对于共生和致病关系都很重要，但在分子水平上往往知之甚少。在宿主压力条件下，人阿片肽强啡肽的水平升高，通过未知途径触发机会致病菌铜绿假单胞菌的毒力。在这里，我们应用多层化学生物学策略来揭示这种假定的界际信号的作用模式。我们设计并应用了强啡肽启发的光亲和探针，通过化学蛋白质组学揭示活细菌中肽的蛋白质靶标。ParS 是一种基本上没有特征的双组件系统膜传感器，被认为是最有希望的产品。随后的完整蛋白质组研究表明，强啡肽 (1-13) 在假单胞菌中诱导抗菌肽样反应，并特异性上调膜防御机制。在 parS 突变体中没有观察到这种反应，它对强啡肽诱导的毒性更敏感。因此，铜绿假单胞菌利用 ParS 传感机制来防御宿主以响应强啡肽作为信号。这项研究强调界际交流是一种潜在的基本策略，不仅可以诱导铜绿假单胞菌的毒力，而且可以在宿主的恶劣环境中维持生存能力。铜绿假单胞菌利用 ParS