N-芴甲氧羰基-D-瓜氨酸 | 200344-33-8

• 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: N-芴甲氧羰基-D-瓜氨酸
• 中文别名: FMOC-氨基酸FMOC-D-CIT-OH；FOMC-D-瓜氨酸；Fmoc-D-瓜氨酸；FMOC-氨基酸
• 英文名称: Fmoc-D-Cit-OH
• 英文别名: (2R)-5-(carbamoylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
• CAS: 200344-33-8
• 化学式: C₂₁H₂₃N₃O₅
• mdl: MFCD00151942
• 分子量: 397.431
• InChiKey: NBMSMZSRTIOFOK-GOSISDBHSA-N

物化性质

• 沸点：
  671.5±55.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储于室温下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-d-cit-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-cit-oh
CAS number: 200344-33-8

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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: C21H23N3O5
Molecular weight: 397.4

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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-瓜氨酸 在 N-甲基吗啉 、 三乙基硅烷 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.83h， 生成 H-Dmt-D-Cit-Aba-β-Ala-NMe-Bn
  参考文献：
  名称：

  Synthesis and biological evaluation of compact, conformationally constrained bifunctional opioid agonist – Neurokinin-1 antagonist peptidomimetics

  摘要：

  A reported mixed opioid agonist neurokinin 1 receptor (NK1R) antagonist 4 (Dmt-D-Arg-Aba-Gly-(3 ',5 '-(CF3)(2))NMe-benzyl) was modified to identify important features in both pharmacophores. The new dual ligands were tested in vitro and subsequently two compounds (lead structure 4 and one of the new analogues 22, Dmt-D-Arg-Aba-beta-Ala-NMe-Bn) were selected for in vivo behavioural assays, which were conducted in acute (tail-flick) and neuropathic pain models (cold plate and von Frey) in rats. Compared to the parent opioid compound 33 (without NK1R pharmacophore), hybrid 22 was more active in the neuropathic pain models. Attenuation of neuropathic pain emerged from NK1R antagonism as demonstrated by the pure NK1R antagonist 6. Surprisingly, despite a lower in vitro activity at NK1R in comparison with 4, compound 22 was more active in the neuropathic pain models. Although potent analgesic effects were observed for 4 and 22, upon chronic administration, both manifested a tolerance profile similar to that of morphine and cross tolerance with morphine in a neuropathic pain model in rat. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.033

文献信息

• Methods for the production of peptide derivatives
  申请人：Tovi Avi

  公开号：US20060276626A1

  公开（公告）日：2006-12-07

  The invention relates to methods for the preparation of peptides which are a C-terminal amide derivatives by a combination of solid-phase synthesis and post assembly solution phase synthesis. The peptides which are a C-terminal amide derivatives are further converted to peptide acetates. The invention also relates to pure peptide acetates and to protected peptide precursors.

  这项发明涉及一种通过固相合成和后组装溶液相合成相结合的方法制备C-末端酰胺衍生物的肽。这些C-末端酰胺衍生物的肽进一步转化为肽醋酸酯。该发明还涉及纯肽醋酸酯和受保护的肽前体。
• Identification of the Natural Product Rotihibin A as a TOR Kinase Signaling Inhibitor by Unbiased Transcriptional Profiling
  作者：Vivek Halder、Julian Oeljeklaus、Geronimo Heilmann、Jan H. Krahn、Yanlin Liu、Yan Xiong、Markus Schlicht、Jasmin Schillinger、Barbara Kracher、Michael Ehrmann、Erich Kombrink、Farnusch Kaschani、Markus Kaiser

  DOI：10.1002/chem.201802647

  日期：2018.8.27

  a rapid, label‐free, and compound economic evaluation of a natural product′s bioactivity profile in a complex multicellular organism. To this end, we established a chemical synthesis of Rotihibin A as well as that of structural analogues, followed by transcriptional profiling‐guided identification and validation of Rotihibin A as a TOR signaling inhibitor (TOR=target of rapamycin). These findings illustrate

  具有生物活性的天然产物是开发用于生物学研究的化学工具的重要起点。为了阐明其生物活性特征，通常使用具有简洁复杂性的生物系统（例如细胞培养系统），而仅在较复杂的多细胞系统中进行无偏研究的情况很少。在这里，我们用天然产物Rotihibin A和植物研究模型系统拟南芥（Arabidopsis thaliana）进行了演示。无偏见的转录谱分析可以对复杂的多细胞生物中的天然产物的生物活性进行快速，无标记的复合经济评估。为此，我们建立了Rotihibin A和结构类似物的化学合成方法，然后进行转录谱分析指导鉴定和验证Rotihibin A作为TOR信号抑制剂（TOR =雷帕霉素的靶标）。这些发现表明，转录谱分析和天然产物研究的组合方法可能代表一种简化了天然产物化学工具开发的技术简单方法，即使对于生物复杂的多细胞生物系统也是如此。
• PROCESS FOR THE PREPARATION OF CETRORELIX ACETATE
  申请人：BIOPHORE INDIA PHARMACEUTICALS PRIVATE LIMITED

  公开号：US20190382447A1

  公开（公告）日：2019-12-19

  The present invention relates to an improved process for the preparation of Cetrorelix acetate (1). More particularly, the present invention relates to the purification of Cetrorelix acetate (1) by simple method.

  本发明涉及一种改进的制备醋酸色素雷利珠的过程。更具体地说，本发明涉及一种简单方法对醋酸色素雷利珠进行纯化。
• A Cyclic Tetrapeptide (“Cyclodal”) and Its Mirror-Image Isomer Are Both High-Affinity μ Opioid Receptor Antagonists
  作者：Grazyna Weltrowska、Thi M.-D. Nguyen、Nga N. Chung、JodiAnne Wood、Xiaoyu Ma、Jason Guo、Brian C. Wilkes、Yang Ge、André Laferrière、Terence J. Coderre、Peter W. Schiller

  DOI：10.1021/acs.jmedchem.6b01200

  日期：2016.10.13

  opioid receptor (MOR) agonist [Dmt1]DALDA (H-Dmt-d-Arg-Phe-Lys-NH2 (9; Dmt = 2′,6′-dimethyltyrosine) resulted in a highly active, selective MOR antagonist, c[-d-Arg-Phe-Lys-Dmt-] (1) (“cyclodal”), with subnanomolar binding affinity. A docking study of cyclodal using the crystal structure of MOR in the inactive form showed a unique binding mode with the two basic residues of the ligand forming salt

  μ阿片受体激动剂[Dmt 1 ] DALDA（H-Dmt- d -Arg-Phe-Lys-NH 2（9 ; Dmt = 2'，6'-二甲基酪氨酸）从头到尾环化导致一种具有高活性的选择性MOR拮抗剂c [ -d -Arg-Phe-Lys-Dmt-]（1）（“环糊精”），具有亚纳摩尔结合亲和力。形式显示出独特的结合模式，配体的两个基本残基与Asp 127和Glu 229形成盐桥受体残基。静脉注射时，摆线针显示出较高的血浆稳定性，并能够穿过血脑屏障以逆转吗啡诱导的中央介导的镇痛作用。出乎意料的是，环化的c [-Arg- d -Phe- d -Lys- d -Dmt-]（2）的镜像异构体（光学对映体）也被证明是具有1 nM结合亲和力的选择性MOR拮抗剂。因此，这两种化合物代表了镜像阿片受体配体的第一个实例，其两个光学对映体均具有高结合亲和力。灭环蛋白中Lys-Dmt肽键的还原产生了具有MOR激动剂活性的类似物c
• WO2020157128A5
  申请人：——

  公开号：WO2020157128A5

  公开（公告）日：2022-12-23