FMOC-7-氨基庚酸 | 127582-76-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - FMOC-氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: FMOC-7-氨基庚酸
• 中文别名: 7-(芴甲氧羰基-氨基)庚酸
• 英文名称: Fmoc-7-aminoheptanoic acid
• 英文别名: 7-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)heptanoic acid；Fmoc-aminoheptanoic acid；7-(Fmoc-amino)heptanoic acid；7-(9H-fluoren-9-ylmethoxycarbonylamino)heptanoic acid
• CAS: 127582-76-7
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: FRPYXTFBPCYALT-UHFFFAOYSA-N

物化性质

• 沸点：
  590.0±33.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  10
• 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

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• WGK Germany：
  3
• 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：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-7-amino-heptanoic acid
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-7-amino-heptanoic acid
CAS number: 127582-76-7

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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-7-氨基庚酸 在 哌啶 、 sodium hydroxide 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 108.5h， 生成 (S)-3-phenyl-2-(3-{2-[6-(tetrahydro-pyran-2-yloxycarbamoyl)-hexyl-carbamoyl]-1H-indol-5-yl}-propionylamino)-propionic acid cyclopentyl ester
  参考文献：
  名称：

  WO2006/117549

  摘要：

  公开号：
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 7-氨基庚酸 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 以89%的产率得到FMOC-7-氨基庚酸
  参考文献：
  名称：

  固定在树脂上的异羟肟酸 (HAIR)：用于合成双靶向 HDAC 抑制剂和 HDAC 降解剂 (PROTAC) 的工具箱。

  摘要：

  通过多靶点药物抑制多个癌症相关途径是现代抗癌药物发现中的一种新兴方法。在这里，基于组蛋白脱乙酰酶抑制剂 (HDACi) 和烷化剂之间已确立的协同作用，我们提出了一系列使用药效团连接策略的烷化 HDACi 的发现。为了并行合成目标化合物，我们开发了一种有效的固相支持方案，使用固定在树脂上的异羟肟酸（HAIR）作为稳定且通用的构建块来制备功能化 HDACi。最有前途的化合物3 n在细胞凋亡诱导、半胱天冬酶 3/7 激活和 DNA 损伤 (γ-H2AX) 形成方面的活性明显高于任一活性成分单独的活性总和。此外，为了证明我们预装树脂的实用性，HAIR 方法成功扩展到概念验证蛋白水解靶向嵌合体 (PROTAC) 的合成，该嵌合体可有效降解组蛋白脱乙酰酶。

  DOI：

  10.1002/anie.202006725

文献信息

• VLA-4 inhibitor compounds
  申请人：Daiichi Pharmaceutical Co., LTD.

  公开号：US20030078249A1

  公开（公告）日：2003-04-24

  Compounds that selectively inhibit the binding of ligands to &agr;4&bgr;1 integrin (VLA-4) and methods for their preparation are disclosed. In one embodiment, compounds of the invention are represented by Formula I: 1 As selective inhibitors of VLA-4 mediated cell adhesion, compounds of the present invention are useful in the treatment of conditions associated with such adhesion, including, but not limited to, such conditions as inflammatory and autoimmune responses, diabetes, asthma, psoriasis, inflammatory bowel disease, transplantation rejection, and tumor metastasis. Also disclosed are pharmaceutical compositions, methods of inhibiting VLA-4 mediated cell adhesion and methods of treating conditions associated with LA-4 mediated cell adhesion, which involve compounds of Formula I.

  本发明公开了选择性抑制配体与α4β1整合素（VLA-4）结合的化合物及其制备方法。在一个实施例中，本发明的化合物由式I表示： 1 作为VLA-4介导的细胞粘附的选择性抑制剂，本发明的化合物可用于治疗与该粘附相关的疾病，包括但不限于炎症和自身免疫反应、糖尿病、哮喘、银屑病、炎症性肠病、移植排斥和肿瘤转移。还公开了包含式I化合物的药物组合物、抑制VLA-4介导的细胞粘附的方法以及治疗与VLA-4介导的细胞粘附相关疾病的方法。
• Optimization of axial ligands to promote the photoactivation of BODIPY-conjugated platinum(<scp>iv</scp>) anticancer prodrugs
  作者：Houzong Yao、Yuliana F. Gunawan、Gongyuan Liu、Man-Kit Tse、Guangyu Zhu

  DOI：10.1039/d1dt02362d

  日期：——

  photoabsorber at the axial position to photoactivate carboplatin-based platinum(IV) complexes. However, the influence of the axial ligands on the photoactivation rate of the platinum center and the subsequent biological activity are still unknown. In this study, we report the design and synthesis of a series of carboplatin-based photoactivable platinum(IV) prodrugs containing BODIPY axial ligands with

  含有轴向羧酸盐的基于卡铂的铂 ( IV ) 前药相对难以还原释放活性铂 ( II ) 物质并杀死癌细胞。为了促进活化过程，二吡咯亚甲基硼 (BODIPY) 配体被用作轴向位置的光吸收剂，以光活化卡铂基铂 ( IV ) 配合物。然而，轴向配体对铂中心光活化速率和随后的生物活性的影响仍然未知。在本研究中，我们报道了一系列含有不同长度的BODIPY轴向配体的卡铂基光活化铂( IV )前药的设计和合成。所得的 BODIPY 共轭铂 ( IV ) 前药OH2C–OH8C在相反的轴向位置带有羟基配体，在黑暗中比相应的含有乙酰基配体的前药AC2C–AC8C稳定性稍差。前药OH3C-OH8C在照射下可在8分钟内光活化，前药AC3C-AC8C的光活化速率进一步提高，仅需20秒。此外，前药AC3C ，其中BODIPY光吸收剂和铂中心之间的连接体具有适当的长度，在乙酰化前药AC2C-AC8C中光活化最快。高细胞
• Small Multivalent Architectures Mimicking Homotrimers of the TNF Superfamily Member CD40L:  Delineating the Relationship between Structure and Effector Function
  作者：Nathalie Trouche、Sébastien Wieckowski、Weimin Sun、Olivier Chaloin、Johan Hoebeke、Sylvie Fournel、Gilles Guichard

  DOI：10.1021/ja073169m

  日期：2007.11.1

  Synthetic multivalent ligands, owing to the presence of multiple copies of a recognition motif attached to a central scaffold, can mediate clustering of cell surface receptors and thereby function as effector molecules. This paper dissects the relationship between structure and effector function of synthetic multivalent ligands targeting CD40, a cell surface receptor of the tumor necrosis factor receptor

  合成的多价配体，由于存在与中央支架相连的识别基序的多个拷贝，可以介导细胞表面受体的聚集，从而起到效应分子的作用。本文剖析了靶向 CD40 的合成多价配体的结构和效应子功能之间的关系，CD40 是肿瘤坏死因子受体 (TNF-R) 超家族的细胞表面受体。在体内触发 CD40 信号可用于增强对细胞内病原体或肿瘤的免疫力。通过系统地改变中央支架的形状和价态、接头的性质和长度以及受体结合基序的序列，已经制备了一系列多聚体分子。此处报告的数据 (i) 表明 CD40 结合单位的径向分布和 C3 对称性是与 CD40 和信号传导的最佳结合的首选，(ii) 强调选择合适的接头将受体结合基序连接到中心的重要性支架，以及 (iii) 展示了平面环状 α 和 β 肽作为 CD40L 模拟物设计模板的多功能性。特别是，(Ahx)3-B 三聚体支架-接头组合同样容纳了来自不同 CD40L 热点区域的结合元件，包括 AA"
• Peptidomimetic inhibitors of<i>N</i>-myristoyltransferase from human malaria and leishmaniasis parasites
  作者：Tayo O. Olaleye、James A. Brannigan、Shirley M. Roberts、Robin J. Leatherbarrow、Anthony J. Wilkinson、Edward W. Tate

  DOI：10.1039/c4ob01669f

  日期：——

  Peptidomimetic inhibitors ofN-myristoyltransferase from malaria and leishmaniasis parasites have been designed with nanomolar potency, and reveal the first direct structural evidence for a ternary NMT/CoA/myristoyl peptide product complex.

  肽类模拟抑制剂已经被设计出来，针对疟疾和利什曼病寄生虫中的N-肟基转移酶，具有纳摩尔级的效力，并展示了第一个直接的结构证据，证明了一个三元复合物NMT/CoA/myristoyl肽产物的存在。
• Arginine-linked neomycin B dimers: synthesis, rRNA binding, and resistance enzyme activity
  作者：Yi Jin、Derrick Watkins、Natalya N. Degtyareva、Keith D. Green、Meredith N. Spano、Sylvie Garneau-Tsodikova、Dev P. Arya

  DOI：10.1039/c5md00427f

  日期：——

  important for maintaining translational fidelity. The bacterial A-site has a small base variation as compared with the human analogue, allowing aminoglycoside (AG) antibiotics to selectively bind within this region of the ribosome and negatively affect microbial protein synthesis. Here, by using a fluorescence displacement screening assay, we demonstrate that neomycin B (NEO) dimers connected by L-arginine-containing

  组成核糖体解码中心的核苷酸是高度保守的，因为它们对于维持翻译保真度很重要。与人类类似物相比，细菌A位点的碱基变异较小，从而使氨基糖苷（AG）抗生素能够选择性地结合在核糖体的该区域内，并对微生物蛋白质的合成产生负面影响。这里，通过使用荧光位移筛选试验，我们表明，新霉素B（NEO）由连接的二聚物大号不同长度和组合物结合的连接体与相比于NEO模型A位的RNA更高的亲和力，与IC含精氨酸- 50值范围在〜40–70 nM之间，并且一定范围的接头长度表明，细菌A位RNA明显优于人类类似物。此外，AG修饰酶（AMEs），例如AG O-磷酸转移酶，在许多类型的传染性细菌中赋予抗生素抗性，它们在体外显示出对某些L-精氨酸连接的NEO二聚体的活性显着降低。这些二聚体对几种细菌菌株的抗微生物活性比其母体NEO弱。