N6-[叔丁氧羰基]-N2-[芴甲氧羰基]-L-赖氨酸 2,5-二氧代-1-吡咯烷基酯 | 132307-50-7

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N6-[叔丁氧羰基]-N2-[芴甲氧羰基]-L-赖氨酸 2,5-二氧代-1-吡咯烷基酯
• 中文别名: N6-[叔丁氧羰基]-N2-[芴甲氧羰基]-L-赖氨酸2,5-二氧代-1-吡咯烷基酯；芴甲氧羰基-N'-叔丁酯-L-赖氨酸琥珀酰亚胺酯
• 英文名称: 2,5-dioxopyrrolidin-1-yl N²-(((9H-fluoren-9-yl)methoxy)carbonyl)-N⁶-(tert-butoxycarbonyl)-L-lysinate
• 英文别名: Fmoc-Lys(Boc)-OSu；(2,5-dioxopyrrolidin-1-yl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 132307-50-7
• 化学式: C₃₀H₃₅N₃O₈
• mdl: MFCD00153359
• 分子量: 565.623
• InChiKey: HONZVSWDWBWWMH-DEOSSOPVSA-N

物化性质

• 熔点：
  147-150°C
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、二甲基甲酰胺（轻微、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.433
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 储存条件：
  存储条件：2-8°C，需密封并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-Lys(Boc)-OSu
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(Boc)-OSu
CAS number: 132307-50-7

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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, under −20◦C.
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: C30H35N3O8
Molecular weight: 565.6

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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：

  N6-[叔丁氧羰基]-N2-[芴甲氧羰基]-L-赖氨酸 2,5-二氧代-1-吡咯烷基酯 在 哌啶 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.25h， 生成 H2N-Lys(Boc)-propargyl amide
  参考文献：
  名称：

  [EN] TUNABLE FLUORESCENCE USING CLEAVABLE LINKERS
  [FR] FLUORESCENCE RÉGLABLE À L'AIDE DE LIEURS CLIVABLES

  摘要：

  这项发明涉及可切割化学反应，特别是利用存在于荧光染料-猝灭剂共轭物中的可切割连接物来实现可调节荧光。

  公开号：

  WO2014171899A1
• 作为产物：
  描述：

  N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 在 N,N'-二环己基碳二亚胺 作用下， 生成 N6-[叔丁氧羰基]-N2-[芴甲氧羰基]-L-赖氨酸 2,5-二氧代-1-吡咯烷基酯
  参考文献：
  名称：

  DRUG-LOADED EMULSION

  摘要：

  本发明涉及一种药物负载乳液，包括以下配方：一种经修饰的疏水助剂，其化学式如下，一种疏水性药物和一种表面活性剂：其中R是一种具有1-3个羟基的疏水性天然化合物或疏水性合成化合物（n=1-3）；R1是α-氨基保护基，R2是氨基酸侧链。当m=0时，R通过酯化与带有保护基的氨基酸衍生物反应，形成携带带有保护基的氨基酸衍生物的疏水助剂；当m=1时，R首先通过酯基与不同链长（l=1、2、4、6）的氨基酸连接臂反应，然后再与带有保护基的氨基酸衍生物反应。

  公开号：

  US20220111056A1

文献信息

• A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols
  作者：Sandip V. Jadhav、Anupam Bandyopadhyay、Sushil N. Benke、Sachitanand M. Mali、Hosahudya N. Gopi

  DOI：10.1039/c0ob01226b

  日期：——

  for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals

  一种简便，高效且无外消旋的方法，使用该方法合成N保护的β-氨基醇和肽醇N-羟基琥珀酰亚胺描述了活性酯。使用这种方法，可以高产率分离出二肽，三肽和五肽醇。分析了β-氨基醇，二肽和三肽醇的晶体构象，在三肽醇晶体中观察到了明确定义的III型β角。发现该方法与Fmoc-，Boc-和其他侧链保护基相容。
• Site-Specific Incorporation of Multiple Thioamide Substitutions into a Peptide Backbone via Solid Phase Peptide Synthesis
  作者：Jinhua Yang、Changliu Wang、Chaochao Yao、Chunqiu Chen、Yafang Hu、Guifeng He、Junfeng Zhao

  DOI：10.1021/acs.joc.9b02486

  日期：2020.2.7

  as novel thioacylating reagents in solid phase peptide synthesis. This method is amenable for 19 of 20 proteinogenic amino acids, His being the exception. One to multiple thioamide substitutions could be incorporated into a growing peptide with no epimerization or a low level of epimerization. By using this method, a fully thioamide-substituted hexapeptide containing up to five continuous thioamide

  在各种肽修饰策略中，通过用硫原子取代酰胺键的羰基氧原子进行硫酰胺取代，对于化学生物学而言是不可估量的工具，可用于肽药物发现和蛋白质结构功能研究。然而，由于缺乏用于位点特异性地将硫酰胺键结合到肽主链中，特别是将多个硫酰胺取代引入到固体支持物上的肽的合成方法，所以尚未对硫酰胺取代作用进行很好的研究。在此，我们报告了一种高效的方法，该方法通过使用α-硫代酰氧基烯酰胺（通过添加N保护的单硫代氨基酸和乙酰胺形成）以位点特异性的方式将硫酰胺键结合到肽主链中，作为固相肽合成中的新型硫酰化试剂。此方法适用于20个蛋白原氨基酸中的19个，His是一个例外。可以将一个至多个硫酰胺取代基掺入正在生长的肽中，而没有差向异构化或低水平的差向异构化。通过使用该方法，可以平滑地合成包含多达五个连续硫代酰胺键的完全硫代酰胺取代的六肽。这种合成方法将刺激硫酰胺取代工具在蛋白质工程和肽药物发现中的应用。可以顺利合成含多达五个
• Hydrogelation and Self-Assembly of Fmoc-Tripeptides: Unexpected Influence of Sequence on Self-Assembled Fibril Structure, and Hydrogel Modulus and Anisotropy
  作者：G. Cheng、V. Castelletto、C. M. Moulton、G. E. Newby、I. W. Hamley

  DOI：10.1021/la903678e

  日期：2010.4.6

  buffer, the former peptide forms highly anisotropic fibrils which show local alignment, and the hydrogels show flow-aligning properties. In contrast, Fmoc-K(Boc)LV forms highly branched fibrils that produce isotropic hydrogels with a much higher modulus (G′ > 104 Pa), and lower concentration for hydrogel formation. The distinct self-assembled structures are ascribed to conformational differences, as

  在硼酸盐缓冲液和其他碱性溶液中，研究了两种Fmoc-三肽[Fmoc = N-（芴基-9-甲氧羰基）]的自组装和水凝胶化性质。在自组装性能的显着的差异，观察比较的Fmoc-VLK（BOC）与Fmoc-K（BOC）LV，既包含K保护由Ñ ε -叔-butyloxycarbonate（BOC）。在硼酸盐缓冲液中，前一种肽形成高度各向异性的原纤维，该原纤维显示局部排列，而水凝胶显示出流动排列特性。相反，Fmoc-K（Boc）LV形成高度支化的原纤维，这些原纤维产生具有更高模量的各向同性水凝胶（G '> 10 4Pa），并降低形成水凝胶的浓度。二级结构探针（CD，FTIR，拉曼光谱）和X射线衍射表明，不同的自组装结构具有构象差异。Fmoc-VLK（Boc）形成定义良好的β片，具有交叉的X射线X射线衍射图，而Fmoc-KLV（Boc）形成未定向的组件，具有多个堆叠的片。当反转三肽序列时，K和V残基的互
• Fluorescent Probes for Single-Step Detection and Proteomic Profiling of Histone Deacetylases
  作者：Yusheng Xie、Jingyan Ge、Haipeng Lei、Bo Peng、Huatang Zhang、Danyang Wang、Sijun Pan、Ganchao Chen、Lanfang Chen、Yi Wang、Quan Hao、Shao Q. Yao、Hongyan Sun

  DOI：10.1021/jacs.6b07334

  日期：2016.12.7

  moiety, resulting in turn-on fluorescence. These designed probes are capable of detecting HDAC activity in a continuous fashion, thereby eliminating the extra step of fluorescence development. Remarkably, the amount of turn-on fluorescence can be as high as 50-fold, which is superior to the existing one-step HDAC fluorescent probes. Inhibition experiments further proved that the probes can serve as useful

  组蛋白去乙酰化酶 (HDAC) 在调节各种生理和病理过程中发挥重要作用。开发能够检测 HDAC 活性的荧光探针有助于进一步阐明 HDAC 在生物学中的作用。在这项研究中，我们首先通过结合 Kac 残基和 O-NBD 基团开发了一组基于活性的荧光探针。在酶促去除 Kac 残基中的乙酰基后，释放的游离胺与 O-NBD 部分发生分子内反应，导致荧光开启。这些设计的探针能够以连续方式检测 HDAC 活性，从而消除荧光发展的额外步骤。值得注意的是，开启荧光量可高达50倍，优于现有的一步式HDAC荧光探针。抑制实验进一步证明，这些探针可以作为筛选 HDAC 抑制剂的有用工具。在这些结果的基础上，我们通过在探针中引入二氮嗪光交联剂，设计了一种双用途荧光探针。由此产生的探针不仅能够报告酶活性，而且能够从复杂的细胞环境中直接识别和捕获蛋白质靶标。通过结合荧光法和凝胶内荧光扫描技术，我们发现使用单个探针可以轻
• 一种改性疏水辅料及其制备方法及其应用
  申请人：浙江智达药业有限公司

  公开号：CN112110834B

  公开（公告）日：2022-10-21

  本发明涉及新型药用辅料和载药脂肪乳的制备，提供了一种疏水辅料，分子式如下：R为带一个到三个羟基(n＝1‑3)的疏水天然化合物或合成化合物；R1为α‑氨基保护基团，R2为氨基酸侧链，其中m＝0，此时R通过酯化与带保护基团的氨基酸衍生物发生反应，形成携带具有保护基团的氨基酸衍生物的疏水辅料；或m＝1，此时R先通过酯基引入一个不同链长的氨基酸连接臂(l＝1，2，4，6)，再引入带保护基团的氨基酸衍生物，形成携带具有保护基团的氨基酸衍生物多肽的疏水辅料。通过上述方法在疏水辅料上引入带芳香或烷氧羰基类或酰基类氨基保护基团的氨基酸衍生物，有利于增加药物在疏水辅料中的溶解度以及提高载药脂肪乳的稳定性。