FMOC-N-D-2-氨基-5-甲基己酸 | 204320-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-N-D-2-氨基-5-甲基己酸
• 中文别名: N-[(9H-芴-9-基甲氧基)羰基]-5-甲基-D-正亮氨酸；FMOC-D-高亮氨酸
• 英文名称: (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-methylhexanoic acid
• 英文别名: Fmoc-D-homoleucine；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methylhexanoic acid
• CAS: 204320-60-5
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: UJOQOPBFLFQOJJ-HXUWFJFHSA-N

物化性质

• 沸点：
  568.1±33.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• 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

• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储条件：2-8℃，请干燥密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-d-homoleucine
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-d-homoleucine
CAS number: 204320-60-5

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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: C22H25NO4
Molecular weight: 367.4

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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

反应信息

• 作为反应物：
  描述：

  FMOC-N-D-2-氨基-5-甲基己酸 、 3-甲氧基-4-(1,3-噁唑)苯胺 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 84.0h， 生成 (R)-2-amino-N-(3-methoxy-4-(oxazol-5-yl)phenyl)-5-methylhexanamide trifluoroacetate
  参考文献：
  名称：

  新型芳基酰胺作为脑渗透接头蛋白 2 相关激酶 1 (AAK1) 抑制剂治疗神经性疼痛的发现、结构-活性关系和体内评价

  摘要：

  有效治疗慢性疼痛，特别是神经性疼痛，没有通常伴随当前可用治疗选择的副作用，是一个显着未满足的医疗需求领域。小鼠基因敲除的表型筛选导致发现接头蛋白 2 相关激酶 1 (AAK1) 是神经性疼痛的潜在治疗靶点。一系列基于芳基酰胺的 AAK1 抑制剂的构效关系的合成和优化导致59的鉴定，这是一种脑渗透性 AAK1 选择性抑制剂，被证明是一种有价值的工具化合物。在小鼠中评估了化合物59对 μ2 磷酸化的抑制。对59 人进行的研究在疼痛模型中证明该化合物在持续性疼痛的 II 期福尔马林模型和大鼠神经性疼痛的慢性收缩损伤诱导模型中是有效的。这些结果表明 AAK1 抑制是治疗神经性疼痛的一种有前途的方法。

  DOI：

  10.1021/acs.jmedchem.1c00472

文献信息

• Polymyxins with Potent Antibacterial Activity against Colistin-Resistant Pathogens: Fine-Tuning Hydrophobicity with Unnatural Amino Acids
  作者：Johan Storm Jørgensen、Elnaz Harifi Mood、Anne Sofie Holst Knap、Simone Eidnes Nielsen、Peter E. Nielsen、Dorota Żabicka、Carina Matias、Ilona Domraceva、Fredrik Björkling、Henrik Franzyk

  DOI：10.1021/acs.jmedchem.3c01908

  日期：2024.1.25

  discernible correlation with their antimicrobial activity. This trend was particularly pronounced for colistin-resistant pathogens. The most active compounds demonstrated competitive activity against a panel of Gram-negative pathogens, while exhibiting low in vitro cytotoxicity. Importantly, most of these hits also retained (or even had increased) potency against colistin-susceptible strains. These findings

  鉴于人类病原体中抗菌素耐药性的普遍性增加，迫切需要针对多重耐药 （MDR） 细菌的抗生素。特别是，对用于治疗严重革兰阴性 MDR 感染的最后手段抗生素粘菌素迅速出现的耐药性至关重要。在这里，探索了一系列含有非天然氨基酸的多粘菌素，一些类似物对大肠杆菌、肺炎克雷伯菌、鲍曼不动杆菌和铜绿假单胞菌表现出优异的抗菌活性。该系列化合物的疏水性（通过在反相分析 HPLC 中的保留性测量）与其抗菌活性表现出明显的相关性。这种趋势对于粘菌素耐药病原体尤为明显。最活跃的化合物对一组革兰氏阴性病原体表现出竞争活性，同时表现出低体外细胞毒性。重要的是，这些命中中的大多数还保留（甚至增加了）对粘菌素敏感菌株的效力。这些发现推断，微调疏水性可能使设计出具有良好活性特征的多粘菌素类似物。
• Discovery, Structure–Activity Relationships, and In Vivo Evaluation of Novel Aryl Amides as Brain Penetrant Adaptor Protein 2-Associated Kinase 1 (AAK1) Inhibitors for the Treatment of Neuropathic Pain
  作者：Richard A Hartz、Vijay T. Ahuja、Susheel J. Nara、C.M. Vijaya Kumar、Jeffrey M. Brown、Linda J. Bristow、Ramkumar Rajamani、Jodi K. Muckelbauer、Daniel Camac、Susan E. Kiefer、Lisa Hunihan、Michael Gulianello、Martin Lewis、Amy Easton、Jonathan S. Lippy、Neha Surti、Sreenivasulu N. Pattipati、Manoj Dokania、Saravanan Elavazhagan、Kumaran Dandapani、Brian D. Hamman、Jason Allen、Walter Kostich、Joanne J. Bronson、John E. Macor、Carolyn D. Dzierba

  DOI：10.1021/acs.jmedchem.1c00472

  日期：2021.8.12

  Effective treatment of chronic pain, in particular neuropathic pain, without the side effects that often accompany currently available treatment options is an area of significant unmet medical need. A phenotypic screen of mouse gene knockouts led to the discovery that adaptor protein 2-associated kinase 1 (AAK1) is a potential therapeutic target for neuropathic pain. The synthesis and optimization

  有效治疗慢性疼痛，特别是神经性疼痛，没有通常伴随当前可用治疗选择的副作用，是一个显着未满足的医疗需求领域。小鼠基因敲除的表型筛选导致发现接头蛋白 2 相关激酶 1 (AAK1) 是神经性疼痛的潜在治疗靶点。一系列基于芳基酰胺的 AAK1 抑制剂的构效关系的合成和优化导致59的鉴定，这是一种脑渗透性 AAK1 选择性抑制剂，被证明是一种有价值的工具化合物。在小鼠中评估了化合物59对 μ2 磷酸化的抑制。对59 人进行的研究在疼痛模型中证明该化合物在持续性疼痛的 II 期福尔马林模型和大鼠神经性疼痛的慢性收缩损伤诱导模型中是有效的。这些结果表明 AAK1 抑制是治疗神经性疼痛的一种有前途的方法。