Fmoc-N’,N’,N’-三甲基-L-赖氨酸氯化物 | 201004-29-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-N’,N’,N’-三甲基-L-赖氨酸氯化物
• 中文别名: N-芴甲氧羰基-N',N',N'-三甲基-L-赖氨酸氯化物；FMOC-N',N',N'-三甲基-L-赖氨酸氯化物；N-芴甲氧羰基-N',N',N'-三甲基-L-赖氨酸盐酸盐
• 英文名称: Fmoc-N-ε-(trimethyl)-L-lysine hydrochloride
• 英文别名: Fmoc-Lys(me₃)-OH chloride；N-[(1S)-1-carboxy-5-(trimethylazaniumyl)pentyl]-1-(9H-fluoren-9-ylmethoxy)methanimidate;hydrochloride
• CAS: 201004-29-7
• 化学式: C₂₄H₃₁N₂O₄*Cl
• 分子量: 446.974
• InChiKey: XUJRNPVABVHOAJ-FTBISJDPSA-N

物化性质

• 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)：
  0.86
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-lys(me)3-oh chloride
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-lys(me)3-oh chloride
CAS number: 201004-29-7

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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: C24H31N2O4.Cl
Molecular weight: 447.0

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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, hydrogen chloride.

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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

用途

Fmoc-Lys-(Me₃)-OH氯化物是一种氨基酸类化合物，常用于多肽合成和药物筛选。

反应信息

• 作为反应物：
  描述：

  Fmoc-N’,N’,N’-三甲基-L-赖氨酸氯化物 、 6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl]-3-[1-({3,5-dimethyl-7-[2-(methylamino)ethoxy]tricyclo[3.3.1.1^3,7]dec-1-yl}methyl)-5-methyl-1H-pyrazol-4-yl]pyridine-2-carboxylic acid 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 N-[(5S)-5-amino-6-{[2-({3-[(4-{6-[8-(1,3-benzothiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl]-2-carboxypyridin-3-yl}-5-methyl-1H-pyrazol-1-yl)methyl]-5,7-dimethyltricyclo[3.3.1.1^3,7]dec-1-yl}oxy)ethyl](methyl)amino}-6-oxohexyl]-N,N-dimethylmethanaminium
  参考文献：
  名称：

  [EN] ANTI-EGFR ANTIBODY DRUG CONJUGATES
  [FR] CONJUGUÉ ANTICORPS-MÉDICAMENT ANTI-EGFR

  摘要：

  本发明涉及抑制Bcl-xL的抗表皮生长因子受体（EGFR）抗体药物偶联物（ADCs），包括所述ADCs的组成和方法。公式（IIa），（IIb），（IIc）

  公开号：

  WO2017214282A1
• 作为产物：
  描述：

  叔丁氧甲酰基-N-ε-二甲基-L-赖氨酸 在 sodium carbonate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 13.0h， 生成 Fmoc-N’,N’,N’-三甲基-L-赖氨酸氯化物
  参考文献：
  名称：

  Development of a Fluorogenic Probe with a Transesterification Switch for Detection of Histone Deacetylase Activity

  摘要：

  Histone deacetylases (HDACs) are key enzymatic regulators of many cellular processes such as gene expression, cell cycle, and tumorigenesis. These enzymes are attractive targets for drug development. However, very few simple methods for monitoring HDAC activity have been reported. Here, we have developed a fluorogenic probe, K4(Ac)-CCB, which consists of the histone H3 peptide containing acetyl-Lys and a coumarin fluorophore with a carbonate ester. By the simple addition of the probe to a HDAC solution, enzyme activity was clearly detected through spontaneous intramolecular transesterification, which renders the probe fluorescent. In addition, K4(Ac)-CCB can be applied to the evaluation of HDAC inhibitor activity. This is the first report to demonstrate the monitoring of HDAC activity by using a one-step procedure. Thus, our novel fluorogenic probe will provide a powerful tool for epigenetic research and the discovery of HDAC-targeted drugs.

  DOI：

  10.1021/ja306045j

文献信息

• [EN] BCL XL INHIBITORY COMPOUNDS HAVING LOW CELL PERMEABILITY AND ANTIBODY DRUG CONJUGATES INCLUDING THE SAME<br/>[FR] COMPOSÉS INHIBITEURS DE BCL XL AYANT UNE FAIBLE PERMÉABILITÉ CELLULAIRE ET CONJUGUÉS ANTICORPS-MÉDICAMENT COMPRENANT CEUX-CI
  申请人：ABBVIE INC

  公开号：WO2016094509A1

  公开（公告）日：2016-06-16

  The present disclosure concerns Bcl-xL inhibitors having low cell permeability, antibody drug conjugates (ADCs) comprising the inhibitors, synthons useful for synthesizing the ADCs, compositions comprising the inhibitors or ADCs, and various methods of using the inhibitors and ADCs.

  本公开涉及具有低细胞渗透性的Bcl-xL抑制剂，包括这些抑制剂的抗体药物结合物（ADCs），用于合成ADCs的合成子，包括这些抑制剂或ADCs的组合物，以及使用这些抑制剂和ADCs的各种方法。
• NON-NUCLEOSIDE ANTI-HEPACIVIRUS AGENTS AND USES THEREOF
  申请人：Boyd A. Vincent

  公开号：US20070021434A1

  公开（公告）日：2007-01-25

  The present dislcosure provides amide-based, non-nucleoside compounds having antiviral activity against Hepacivirus, such as hepatitis C virus (HCV), methods and intermediates for synthesizing such compounds, and methods of using the compounds in a variety of contexts, including in the treatment and prevention of viral infections. The present dislcosure also provides methods for identifying amide-based, non-nucleoside compounds having antiviral activity.

  本公开提供了基于酰胺的非核苷类化合物，具有抗Hepacivirus活性，例如丙型肝炎病毒（HCV），合成这类化合物的方法和中间体，以及在各种情境中使用这些化合物的方法，包括在治疗和预防病毒感染中的应用。本公开还提供了识别具有抗病毒活性的基于酰胺的非核苷类化合物的方法。
• COMPOSITIONS AND METHODS FOR TREATING HYPERPROLIFERATIVE DISEASE
  申请人：Cameron Dale Russell

  公开号：US20080171783A1

  公开（公告）日：2008-07-17

  The present disclosure provides amide-based, non-nucleoside compounds having an inhibitory activity against endogenous polymerases, such as polymerase alpha and polymerase gamma. This disclosure further provides uses of treating hyperproliferative diseases or disorders, such as benign or malignant neoplasms, and more specifically cancers that are sensitive to inhibition of polymerase alpha and polymerase gamma.

  本公开提供了基于酰胺的非核苷类化合物，具有对内源聚合酶（如聚合酶α和聚合酶γ）的抑制活性。本公开进一步提供了用于治疗过度增殖性疾病或疾病的用途，例如良性或恶性肿瘤，更具体地是对聚合酶α和聚合酶γ抑制敏感的癌症。
• Synthesis and in Vitro and in Vivo Evaluation of SiFA-Tagged Bombesin and RGD Peptides as Tumor Imaging Probes for Positron Emission Tomography
  作者：Simon Lindner、Christina Michler、Stephanie Leidner、Christian Rensch、Carmen Wängler、Ralf Schirrmacher、Peter Bartenstein、Björn Wängler

  DOI：10.1021/bc400588e

  日期：2014.4.16

  arginine-glycine-aspartic acid) peptides as specific αvβ3 binders were synthesized and tagged with a silicon-fluorine-acceptor (SiFA) moiety. The SiFA synthon allows for a fast and highly efficient isotopic exchange reaction at room temperature giving the [18F]fluoride labeled peptides in up to 62% radiochemical yields (d.c.) and ≥99% radiochemical purity in a total synthesis time of less than 20 min. Using

  胃泌素释放肽（GRP） -受体和α v β 3个-intEGrins作为与正电子发射断层扫描（PET）成像肿瘤潜在目标结构广泛的讨论。由于肿瘤细胞表面受体的过度表达，使用高度特异性的放射性标记受体配体可以实现良好的成像特性。PEG化的铃蟾肽（PESIN）衍生物作为具体的GRP受体配体和RGD（精氨酸-甘氨酸-天门冬氨酸的单字母代码）肽作为具体α v β 3个结合物合成和标记的与硅-氟-受体（SIFA）部分。SiFA synthon可以在室温下进行快速高效的同位素交换反应，从而得到[ 18F]氟化物标记的肽，在不到20分钟的总合成时间内，放射化学产率（dc）高达62％，放射化学纯度≥99％。使用纳摩尔量的前体，可获得高达60 GBqμmol –1的高比活。为了补偿SiFA部分的高亲脂性，引入了各种亲水结构修饰，从而导致logD值显着降低。与PESIN衍生物竞争性置换的实验表明在32至6nm亲
• Chemical Synthesis of Cys-Containing Protein via Chemoselective Deprotection with Different Palladium Complexes
  作者：Naoki Kamo、Gosuke Hayashi、Akimitsu Okamoto

  DOI：10.1021/acs.orglett.9b03152

  日期：2019.10.18

  protecting groups using different palladium complexes to facilitate the efficient chemical protein synthesis. Utilizing the orthogonal deprotection pairs, we accomplished chemical synthesis of histone H3 containing trimethylated Lys through the combination of Pd(0)-mediated Alloc deprotection for one-pot multiple peptide ligation and Pd(II)Cl2-mediated Acm deprotection to recover native Cys residues after

  我们报告使用不同的钯配合物，以促进有效的化学蛋白质合成选择性去除N末端和内部Cys保护基团。利用正交脱保护对，我们通过Pd（0）介导的Alloc脱保护用于一锅多肽连接和Pd（II）Cl 2介导的Acm脱保护的结合，完成了包含三甲基化Lys的组蛋白H3的化学合成，以恢复天然Cys脱硫后的残留物。