N-ALPHA-(9-芴甲氧羰基)-L-BETA-环戊基甘氨酸 | 220497-61-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-ALPHA-(9-芴甲氧羰基)-L-BETA-环戊基甘氨酸
• 中文别名: Fmoc-L-环戊基甘氨酸
• 英文名称: (2S)-2-cyclopentyl-2-[9H-fluoren-9-ylmethoxycarbonylamino]acetic acid
• 英文别名: Fmoc-L-cyclopentylglycine；Fmoc-Cpg-OH；Fmoc-Gly(cPent)-OH；(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-cyclopentylacetic acid；(2S)-2-cyclopentyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)acetic acid
• CAS: 220497-61-0
• 化学式: C₂₂H₂₃NO₄
• 分子量: 365.429
• InChiKey: JGWHUIQSEKGLAQ-FQEVSTJZSA-N

物化性质

• 沸点：
  590.5±33.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  -15°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-cyclopentyl-Gly-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-cyclopentyl-Gly-OH
CAS number: 220497-61-0

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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: C22H23NO4
Molecular weight: 365.4

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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 CPG OH是甘氨酸（HY-Y0966）的衍生物。

反应信息

• 作为反应物：
  描述：

  N-ALPHA-(9-芴甲氧羰基)-L-BETA-环戊基甘氨酸 在 三乙基硅烷 、 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 20.0h， 生成 (2S)-2-cyclopentyl-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]acetic acid
  参考文献：
  名称：

  JP6880352

  摘要：

  公开号：
• 作为产物：
  描述：

  碘代环戊烷 在 palladium dichloride 氢气 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 六甲基磷酰三胺 、 水 为溶剂， -78.0~40.0 ℃ 、413.68 kPa 条件下， 反应 48.0h， 生成 N-ALPHA-(9-芴甲氧羰基)-L-BETA-环戊基甘氨酸
  参考文献：
  名称：

  通过甘氨酸烯醇盐等效物的非对映选择性烷基化有效合成Fmoc-1-环戊基甘氨酸

  摘要：

  用环戊基碘化物将苄基（2 R，3 S）-（-）-6-氧代-2,3-二苯基-4-吗啉羧酸酯（1）衍生的烯醇化物进行立体选择性烷基化，得到抗α-单取代产物苄基（2 R，3 S，5 S）-（-）-6-氧代-2,3-二苯基-5-环戊基-4-吗啉代羧酸盐（3），产率为60％。在PdCl 2上的催化氢解裂解了辅助环系统，以84％的产率得到了1-环戊基甘氨酸（4）。随后用Fmoc-OSu保护α-氨基官能团以高收率得到了Fmoc-1-环戊基甘氨酸（5）。

  DOI：

  10.1016/s0040-4039(03)00370-8

文献信息

• [EN] EPHA4 CYCLIC PEPTIDE ANTAGONISTS AND METHODS OF USE THEREOF<br/>[FR] ANTAGONISTES PEPTIDIQUES CYCLIQUES DE L'EPHA4 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：IRON HORSE THERAPEUTICS INC

  公开号：WO2019213620A1

  公开（公告）日：2019-11-07

  Disclosed herein are compounds and methods of use thereof for the modulation of EphA4 receptor activity. In an aspect, is provided a method of treating or preventing a disease or disorder mediated by EphA4, comprising administering to a subject in need thereof a therapeutically effective amount of a compound as described herein, including certain embodiments, or the structural Formula (I), (l-A), (II), (III), (IV), (IV-1), (V), (Vl-A), (Vl-B), (VII-1), (VII-2), (VIII-1), or (VIII-2), or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof; or a pharmaceutically acceptable salt, solvate, or hydrate thereof.

  本文揭示了化合物及其使用方法，用于调节EphA4受体活性。在一个方面，提供了一种治疗或预防由EphA4介导的疾病或紊乱的方法，包括向需要的受试者施用本文描述的化合物的治疗有效量，包括某些实施例，或结构式(I)，(l-A)，(II)，(III)，(IV)，(IV-1)，(V)，(Vl-A)，(Vl-B)，(VII-1)，(VII-2)，(VIII-1)，或(VIII-2)，或其对映体，对映体混合物，两个或更多对映异构体混合物，或其同位素变体；或其药学上可接受的盐，溶剂合物或水合物。
• [EN] SMALL MOLECULE DCN1 INHIBITORS AND THERAPEUTIC METHODS USING THE SAME<br/>[FR] INHIBITEURS DE DCN1 À PETITES MOLÉCULES ET PROCÉDÉS THÉRAPEUTIQUES LES UTILISANT
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2018183411A1

  公开（公告）日：2018-10-04

  Compounds of formula (I) as inhibitors of DCNl and compositions containing the same are disclosed. Methods of using the DCNl inhibitors in the treatment of diseases and conditions wherein inhibition of DCNl provides a benefit, like oxidative stress-related diseases and conditions, neurodegenerative diseases and conditions, metabolic disorders, and muscular nerve degeneration, also are disclosed.

  公式（I）的化合物被披露为DCNl的抑制剂，以及含有这些化合物的组合物。还披露了在治疗疾病和病况中使用DCNl抑制剂的方法，其中DCNl的抑制提供益处，如氧化应激相关的疾病和病况、神经退行性疾病和病况、代谢紊乱以及肌肉神经退化。
• Optimization of Ligands Using Focused DNA-Encoded Libraries To Develop a Selective, Cell-Permeable CBX8 Chromodomain Inhibitor
  作者：Sijie Wang、Kyle E. Denton、Kathryn F. Hobbs、Tyler Weaver、James M. B. McFarlane、Katelyn E. Connelly、Michael C. Gignac、Natalia Milosevich、Fraser Hof、Irina Paci、Catherine A. Musselman、Emily C. Dykhuizen、Casey J. Krusemark

  DOI：10.1021/acschembio.9b00654

  日期：2020.1.17

  obstacle in developing selective CBX ChD inhibitors. Here we report the selection of small, focused, DNA-encoded libraries (DELs) against multiple homologous ChDs to identify modifications to a parental ligand that confer both selectivity and potency for the ChD of CBX8. This on-DNA, medicinal chemistry approach enabled the development of SW2_110A, a selective, cell-permeable inhibitor of the CBX8 ChD. SW2_110A

  聚梳抑制复合物1（PRC1）对于在发育过程中介导基因表达至关重要。五个色盒（CBX）同源蛋白CBX2，CBX4，CBX6，CBX7和CBX8被整合到PRC1复合物中，它们通过N端染色体结构域（ChD）介导对组蛋白H3（H3K27me3）的三甲基赖氨酸27的靶向作用。个别的CBX旁系同源物已被认为是癌症的药物靶标。然而，CBX ChD之间序列和结构的高度相似性为开发选择性CBX ChD抑制剂提供了主要障碍。在这里，我们报告针对多个同源ChD的小型，集中，DNA编码文库（DEL）的选择，以鉴定对亲本配体的修饰，从而赋予CBX8 ChD选择性和效力。这种基于DNA的药物化学方法使SW2_110A（一种选择性的，CBX8 ChD的细胞可渗透抑制剂。SW2_110A以800 nM的Kd结合CBX8 ChD，在体外对CBX8 ChD的选择性是其他所有CBX同源物的5倍。SW2_110A特异性抑制细胞中
• Structural and mechanistic insights into the inhibition of amyloid-β aggregation by Aβ39-42 fragment derived synthetic peptides
  作者：Akshay Kapadia、Krishna K. Sharma、Indresh Kumar Maurya、Varinder Singh、Madhu Khullar、Rahul Jain

  DOI：10.1016/j.ejmech.2020.113126

  日期：2021.2

  permeability and offered proteolytic stability to the synthetic peptides. Several peptides exhibited promising protection against Aβ aggregation-mediated-neurotoxicity in PC-12 cells at doses ranged between 10 μM and 0.1 μM, further confirmed by the thioflavin-T fluorescence assay. CD study illustrate that these peptides restrict the β-sheet formation, and the non-appearance of Aβ42 fibrillar structures in

  淀粉样-β（Aβ）聚集的抑制是治疗阿尔茨海默氏病（AD）的有前途的方法。合成了基于亲本Aβ肽的Aβ39-42 C末端片段的38个四肽。使用非天然氨基酸的顺序替换/修饰赋予了支架多样性，增强的活性，增强的血脑屏障通透性并为合成肽提供了蛋白水解稳定性。硫黄素-T荧光测定进一步证实了几种肽在PC-12细胞中对Aβ聚集介导的神经毒性具有有希望的保护作用，剂量范围为10μM至0.1μM。CD研究表明，这些肽限制了β-折叠的形成以及Aβ42的不出现电镜中的原纤维结构证实了对Aβ42聚集的抑制。HRMS和ANS荧光光谱分析提供了更多的机理见解。两种选择的前导肽5和16表现出增强的血脑渗透性以及对血清和蛋白水解酶的稳定性。通过计算研究了在Aβ的单体和原纤维单元上的配体-Aβ相互作用的结构见解。前导肽的潜在抑制潜力和短序列为AD的肽衍生疗法的发展提供了新途径。
• SUBSTITUTED-6,8-DIOXABICYCLO[3.2.1]OCTANE-2,3-DIOL COMPOUNDS AS TARGETING AGENTS OF ASGPR
  申请人：Pfizer Inc.

  公开号：US20150329555A1

  公开（公告）日：2015-11-19

  Compounds of Formula (A) are described herein and the uses thereof for the treatment of diseases, conditions and/or disorders mediated by pharmaceutical compositions and the uses thereof as asialoglycoprotein receptor (ASGPR) targeting agents.

  公式（A）的化合物在本文件中被描述，以及它们用于治疗由药物组合物介导的疾病、状况和/或紊乱的使用，以及它们作为阿索糖蛋白受体（ASGPR）靶向剂的使用。