L-(+)-Fmoc-鸟氨酸盐酸盐 | 201046-57-3

• 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: L-(+)-Fmoc-鸟氨酸盐酸盐
• 中文别名: L-(+)-芴甲氧羰基鸟氨酸盐酸盐；L(+)-Fmoc-鸟氨酸盐酸盐
• 英文名称: N^α-Fmoc-N^δ-L-ornithine hydrochloride
• 英文别名: Fmoc-Orn-OH hydrochloride；(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-aminopentanoic acid hydrochloride；(2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;hydrochloride
• CAS: 201046-57-3
• 化学式: C₂₀H₂₂N₂O₄*ClH
• 分子量: 390.867
• InChiKey: RGRQRWUUJPISQG-FERBBOLQSA-N

物化性质

• 熔点：
  97.86 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102
• 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: L(+)-Fmoc-ornithine HCl
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: L(+)-Fmoc-ornithine HCl
CAS number: 201046-57-3

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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, refrigerated.
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: C20H22N2O4.ClH
Molecular weight: 390.9

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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

反应信息

• 作为反应物：
  描述：

  L-(+)-Fmoc-鸟氨酸盐酸盐 在 1H-咪唑-1-磺酰叠氮盐酸盐 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 以53%的产率得到(S)-5-叠氮-2-(芴甲氧羰基-氨基)戊酸
  参考文献：
  名称：

  水溶性，稳定且可与叠氮化物反应的应变二炔，用于生物相容性双应变促进的咔嗒化学反应。

  摘要：

  Sondheimer二炔被广泛用于双应变促进的叠氮化物-炔烃环加成反应中。该试剂的水溶性差，并且在水溶液中迅速分解。这从本质上限制了它在生物系统中的应用，目前还没有有效的解决方案。在这里，我们报告了新型的高度水溶性，稳定和叠氮化物反应性应变二炔试剂的发展。为了证明其广泛的用途，我们将我们的新型二炔应用于双重菌株促进的大环化策略，以生成功能化的基于p53的钉合肽，以抑制致癌性p53-MDM2相互作用。这些功能化的固定肽以低纳摩尔亲和力结合MDM2，并在细胞环境中显示p53激活。总的来说，我们的溶解度高

  DOI：

  10.1039/c9ob01745c
• 作为产物：
  描述：

  L-鸟氨酸盐酸盐 在 盐酸 、 sodium hydroxide 、 copper diacetate 、 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 47.5h， 生成 L-(+)-Fmoc-鸟氨酸盐酸盐
  参考文献：
  名称：

  Masiukiewicz, Elzbieta; Wiejak, Stanislaw; Rzeszotarska, Barbara, Organic Preparations and Procedures International, 2002, vol. 34, # 5, p. 531 - 537

  摘要：

  DOI：

文献信息

• Oxime Side-Chain Cross-Links in an α-Helical Coiled-Coil Protein: Structure, Thermodynamics, and Folding-Templated Synthesis of Bicyclic Species
  作者：Conor M. Haney、W. Seth Horne

  DOI：10.1002/chem.201300506

  日期：2013.8.19

  method to control peptide folding, particularly when α‐helical secondary structure is the target. Here, we examine the application of oxime bridges, formed by the chemoselective reaction between aminooxy and aldehyde side chains, for the stabilization of a helical peptide involved in a protein–protein complex. A series of sequence variants of the dimeric coiled coil GCN4‐p1 bearing oxime bridges at

  共价侧链交联是控制肽折叠的一种通用方法，尤其是当以α螺旋二级结构为目标时。在这里，我们研究了由氨氧基和醛侧链之间的化学选择性反应形成的肟桥对稳定参与蛋白质-蛋白质复合物的螺旋肽的作用。制备了一系列二聚体卷曲螺旋GCN4-p1在肟暴露位置带有肟桥的序列变体，并对其进行了生物学上的表征。在折叠后的蛋白质复合物中，在pH 7时，触发的侧链醛基团的原位暴露和随后的环化反应迅速而干净地进行。一系列不同的肟桥之间的折叠热力学比较表明，交叉链始终稳定在盘绕的线圈上，稳定程度对大环的确切大小和结构敏感。X射线晶体学分析对具有最佳交联位置的螺旋形线圈及其线性前驱体的第二种结构进行了研究，结果表明该桥是如何容纳在α螺旋中的。通过同时在原位同时形成两个键来制备双环低聚物，证明了潜在地利用触发的肟形成来捕获和稳定结合状态下的特定肽折叠构象。
• Preparation of novel alkylated arginine derivatives suitable for click-cycloaddition chemistry and their incorporation into pseudosubstrate- and bisubstrate-based kinase inhibitors
  作者：Jeroen van Ameijde、Alex J. Poot、Loek T. M. van Wandelen、Angelique E. M. Wammes、Rob Ruijtenbeek、Dirk T. S. Rijkers、Rob M. J. Liskamp

  DOI：10.1039/b922928k

  日期：——

  Efficient strategies for the introduction of arginine residues featuring acetylene or azide moieties in their side chains are described. The substituents are introduced in a way that maintains the basicity of the guanidine moiety. The methodology can be used e.g. for non-invasive labeling of arginine-containing peptides. Its applicability is demonstrated by the introduction of ‘click’ handles into a Protein Kinase C (PKC) pseudosubstrate peptide, and the subsequent preparation and evaluation of a novel bisubstrate-based inhibitor based on such a peptide.

  本文介绍了在精氨酸残基侧链中引入乙炔或叠氮取代基的有效策略。取代基的引入可保持胍基的碱性。该方法可用于含精氨酸肽的非侵入性标记。通过在蛋白激酶 C (PKC) 伪底物多肽中引入 "点击 "处理，以及随后制备和评估基于这种多肽的新型双底物抑制剂，证明了该方法的适用性。
• Recognition of shorter and longer trimethyllysine analogues by epigenetic reader proteins
  作者：Abbas H. K. Al Temimi、Roman Belle、Kiran Kumar、Jordi Poater、Peter Betlem、Bas J. G. E. Pieters、Robert S. Paton、F. Matthias Bickelhaupt、Jasmin Mecinović

  DOI：10.1039/c8cc01009a

  日期：——

  Combined thermodynamic data, molecular dynamics simulations, and quantum chemical studies reveal that epigenetic reader proteins efficiently bind trimethylornithine and trimethylhomolysine.

  结合热力学数据、分子动力学模拟和量子化学研究揭示了表观遗传读取蛋白高效地结合了三甲基鸟氨酸和三甲基同赖氨酸。
• Histidine Analog Amino Acids Providing Metal-Binding Sites Derived from Bioinorganic Model Systems
  作者：André Nadler、Christina Hain、Ulf Diederichsen

  DOI：10.1002/ejoc.200900472

  日期：2009.9

  Metalloproteins are of utmost importance for nearly all biological processes. Valuable information about their functionalities came from mutagenesis studies and led to the de novo design of artificial proteins. Advances in peptide chemistry enable the total synthesis of complete proteins and allow the incorporation of non-proteinogenic amino acids. Chelating amino acids utilized to introduce artificial

  金属蛋白对于几乎所有的生物过程都至关重要。关于其功能的宝贵信息来自诱变研究，并导致了人工蛋白质的从头设计。肽化学的进步使完整蛋白质的全合成成为可能，并允许掺入非蛋白氨基酸。用于将人工金属结合位点引入蛋白质的螯合氨基酸应模拟天然残基的侧链，以尽量减少目标蛋白质内的结构后果。在本文中，描述了一种合成方法，用于制备带有通过三唑形成连接到 β-碳的金属配体系统的氨基酸。因此，产生了一个组氨酸异构体，在肽骨架附近有一个额外的金属结合位点。
• An Efficient and Economical Method for the Preparation of Fmoc-Argω,ω′(Boc)2-OH
  作者：Ruixin Zhu、Ming Xie、Fei Wang、Qi Liu、Tingguo Kang

  DOI：10.1002/cjoc.201090257

  日期：——

  The arginine derivative Fmoc‐Argω,ω′(Boc)2‐OH has been prepared in perfect yield starting from Fmoc‐Orn·HCl and N,N′‐di‐Boc‐N′′‐triflyguanidine with the presence of diisopropylethylamine (DIEA). This work provides an efficient and economical method for the preparation of this compound.

  精氨酸衍生物的Fmoc精氨酸ω，ω '（BOC）2 -OH已经完善收率由Fmoc-ORN·HCl和开始制备Ñ，N' -二-制备Boc- N'' -triflyguanidine与二异丙基乙胺的存在下（ DIEA）。这项工作为制备该化合物提供了一种有效而经济的方法。