N-[芴甲氧羰基]-D-谷氨酸 5-(2-丙烯基)酯 | 204251-33-2

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 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: N-[芴甲氧羰基]-D-谷氨酸 5-(2-丙烯基)酯
• 中文别名: N-[芴甲氧羰基]-D-谷氨酸5-(2-丙烯基)酯；N-芴甲氧羰基-D-谷氨酸5-烯丙基酯；FMOC-D-谷氨酸(烯丙酯)
• 英文名称: Fmoc-D-Glu(OAll)-OH
• 英文别名: (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid
• CAS: 204251-33-2
• 化学式: C₂₃H₂₃NO₆
• 分子量: 409.439
• InChiKey: LRBARFFNYOKIAX-HXUWFJFHSA-N

物化性质

• 沸点：
  650.1±55.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-d-glu(oall)-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-d-glu(oall)-oh
CAS number: 204251-33-2

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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: C23H23NO6
Molecular weight: 409.4

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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：

  N-[芴甲氧羰基]-D-谷氨酸 5-(2-丙烯基)酯 在 四(三苯基膦)钯 苯硅烷 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-芴甲氧羰基-D-谷氨酸1-甲酯
  参考文献：
  名称：

  基于结节蛋白和微囊藻毒素毒素结构的丝氨酸-苏氨酸蛋白磷酸酶抑制剂的设计和制备。第三部分

  摘要：

  结节菌素和微囊藻毒素是复杂的天然环状异肽肝毒素，可作为真核丝氨酸-苏氨酸蛋白磷酸酶PP1和PP2A的亚纳摩尔抑制剂，这些酶密切参与控制细胞代谢。以前，我们描述了剥离的结核菌素类似物的溶液相合成。环[-β-Ala-（R）-Glu-α-OMe-γ-Sar-（R）-Asp-α-OMe-β-（S）-Phe-] 3和环[-（3 R）- 3-羟甲基-β-Ala-（R）-Glu-α-OMe-γ-Sar-（R）-Asp-α-OMe-β-（S）-Phe-] 5。综合策略旨在允许宏环化后的阐述。在这里，我们研究了引入多样性并实现大环内酰胺化的替代方法，并比较了大环化合物的固相和固相肽合成的相对效率。大环环{-[（（2 R）-α-4-苄基哌啶基酰胺基-Asp] -β-[（R）-Glu ] -Sar -[（R -Asp ）-β-]大环的合成及生物学活性（S）-Phe-} 29和环{-（2 S）-Phe-[（2 R

  DOI：

  10.1039/b100401h
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 γ-allyl (2R)-glutamate hydrochloride 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以100%的产率得到N-[芴甲氧羰基]-D-谷氨酸 5-(2-丙烯基)酯
  参考文献：
  名称：

  基于结节蛋白和微囊藻毒素毒素结构的丝氨酸-苏氨酸蛋白磷酸酶抑制剂的设计和制备。第三部分

  摘要：

  结节菌素和微囊藻毒素是复杂的天然环状异肽肝毒素，可作为真核丝氨酸-苏氨酸蛋白磷酸酶PP1和PP2A的亚纳摩尔抑制剂，这些酶密切参与控制细胞代谢。以前，我们描述了剥离的结核菌素类似物的溶液相合成。环[-β-Ala-（R）-Glu-α-OMe-γ-Sar-（R）-Asp-α-OMe-β-（S）-Phe-] 3和环[-（3 R）- 3-羟甲基-β-Ala-（R）-Glu-α-OMe-γ-Sar-（R）-Asp-α-OMe-β-（S）-Phe-] 5。综合策略旨在允许宏环化后的阐述。在这里，我们研究了引入多样性并实现大环内酰胺化的替代方法，并比较了大环化合物的固相和固相肽合成的相对效率。大环环{-[（（2 R）-α-4-苄基哌啶基酰胺基-Asp] -β-[（R）-Glu ] -Sar -[（R -Asp ）-β-]大环的合成及生物学活性（S）-Phe-} 29和环{-（2 S）-Phe-[（2 R

  DOI：

  10.1039/b100401h

文献信息

• [EN] NOVEL RADIOLABELLED CXCR4-TARGETING COMPOUNDS FOR DIAGNOSIS AND THERAPY<br/>[FR] NOUVEAUX COMPOSÉS RADIOMARQUÉS DIAGNOSTIQUES ET THÉRAPEUTIQUES CIBLANT CXCR4
  申请人：PROVINCIAL HEALTH SERVICES AUTHORITY

  公开号：WO2020210919A1

  公开（公告）日：2020-10-22

  This application relates to compounds of Formula (I): [targeting peptide]-N(R1)-X1(R2)L1-[linker]-RX n1 (I). The targeting peptide is cyclo[L-Phe-L-Tyr-L-Lys(iPr)-D-Arg-L-2-Nal-Gly-D-Glu]-L-Lys(iPr). R1 is H or methyl. X1 is an optionally substituted C1-C15 hydrocarbon optionally comprising heteroatoms. R2 is C(O)OH or C(O)NH2. L1 is a linkage (thiolether, amide, maleimide-thiol, triazole). The linker has a net negative charge at physiological pH and is a linear or branched chain of 1-10 units of X2L2 and/or X2(L2)2, wherein: each X2 is, independently, an optionally substituted C1-C15 hydrocarbon optionally comprising heteroatoms; and each L2 is a linkage. The linker optionally further comprises an albumin binder bonded to an L2. Each RX is a radiolabelling group linked through a separate L2, selected from: a metal chelator; a prosthetic group containing trifluoroborate (BF3); or a prosthetic group containing a silicon-fluorine-acceptor moiety. The compounds may be useful for imaging CXCR4-expressing tissues or for treating CXCR4-associated diseases or conditions (e.g. cancer).

  这个应用涉及到Formula (I)的化合物：[靶向肽]-N(R1)-X1(R2)L1-[连接物]-RX n1 (I)。靶向肽是cyclo[L-Phe-L-Tyr-L-Lys(iPr)-D-Arg-L-2-Nal-Gly-D-Glu]-L-Lys(iPr)。R1是H或甲基。X1是一个可选择地取代的含有杂原子的C1-C15烃。R2是C(O)OH或C(O)NH2。L1是一个连接物（硫醚、酰胺、马来酰亚胺-硫醇、三唑）。连接物在生理pH下具有净负电荷，是由1-10个X2L2和/或X2(L2)2的线性或支链构成，其中：每个X2独立地是一个可选择地取代的含有杂原子的C1-C15烃；每个L2是一个连接物。连接物可选择地进一步包括与L2结合的白蛋白结合剂。每个RX是通过单独的L2连接的放射标记基团，选自：金属螯合剂；含三氟硼酸盐（BF3）的假体基团；或含硅-氟受体基团的假体基团。这些化合物可能对于成像CXCR4表达组织或治疗与CXCR4相关的疾病或症状（如癌症）有用。
• Antifungal and Antibiofilm Activity of Cyclic Temporin L Peptide Analogues against Albicans and Non-Albicans Candida Species
  作者：Rosa Bellavita、Angela Maione、Francesco Merlino、Antonietta Siciliano、Principia Dardano、Luca De Stefano、Stefania Galdiero、Emilia Galdiero、Paolo Grieco、Annarita Falanga

  DOI：10.3390/pharmaceutics14020454

  日期：——

  Temporins are one of the largest families of antimicrobial peptides with both anti-inflammatory and antimicrobial activity. Herein, for a panel of cyclic temporin L isoform analogues, the antifungal and antibiofilm activities were determined against representative Candida strains, including C. albicans, C. glabrata, C. auris, C. parapsilosis and C. tropicalis. The outcomes indicated a significant anti-candida

  Temporins 是最大的抗菌肽家族之一，具有抗炎和抗菌活性。在此，对于一组环状 temporin L 同工型类似物，针对代表性念珠菌菌株（包括白色念珠菌、光滑念珠菌、耳念珠菌、近平滑念珠菌和热带念珠菌）测定了抗真菌和抗生物膜活性。结果表明四种肽（3、7、15 和 16）对浮游和生物膜生长具有显着的抗念珠菌活性。使用大毒蛾幼虫在体内评估了高浓度无毒性和感染后的存活率，并通过荧光测定和圆二色性 (CD) 研究了构象和细胞毒性之间的相关性。通过结合荧光光谱、CD、动态光散射、共聚焦和原子力显微镜，假设了四种类似物的作用方式。结果表明，肽 3 以无毒化合物的形式出现，显示出有效的抗生物膜活性，代表了一种有前途的生物医学应用化合物。
• [EN] NOVEL CXCR4-TARGETING COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS CIBLANT CXCR4
  申请人：PROVINCIAL HEALTH SERVICES AUTHORITY

  公开号：WO2022082312A1

  公开（公告）日：2022-04-28

  The present disclosure relates to peptidic compounds of Formula A, A-II, A-III, B, or C, or salt or solvate thereof, compositions thereof, and methods of use thereof. The compounds of the present disclosure are useful for targeting CXCR4 for purposes such as imaging and/or therapeutics.

  本公开涉及A，A-II，A-III，B或C的肽化合物，或其盐或溶剂，以及其组合物和使用方法。本公开的化合物可用于针对CXCR4进行成像和/或治疗等目的。
• [EN] CD38-BINDING AGENTS AND USES THEREOF<br/>[FR] AGENT DE LIAISON À CD38 ET UTILISATIONS ASSOCIÉES
  申请人：KLEO PHARMACEUTICALS INC

  公开号：WO2021003050A3

  公开（公告）日：2021-02-11
• In silico scaffold evaluation and solid phase approach to identify new gelatinase inhibitors
  作者：Alessandra Topai、Perla Breccia、Franco Minissi、Alessandro Padova、Stefano Marini、Ilaria Cerbara

  DOI：10.1016/j.bmc.2012.02.010

  日期：2012.4

  Among matrix metalloproteinases (MMPs), gelatinases MMP-2 (gelatinase A) and MMP-9 (gelatinase B) play a key role in a number of physiological processes such as tissue repair and fibrosis. Many evidences point out their involvement in a series of pathological events, such as arthritis, multiple sclerosis, cardiovascular diseases, inflammatory processes and tumor progression by degradation of the extracellular matrix. To date, the identification of non-specific MMP inhibitors has made difficult the selective targeting of gelatinases. In this work we report the identification, design and synthesis of new gelatinase inhibitors with appropriate drug-like properties and good profile in terms of affinity and selectivity. By a detailed in silico protocol and innovative and versatile solid phase approaches, a series of 4-thiazolydinyl-N-hydroxycarboxyamide derivatives were identified. In particular, compounds 9a and 10a showed a potent inhibitory activity against gelatinase B and good selectivity over the other MMP considered in this study. The identified compounds could represent novel potential candidates as therapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.