2-((((9H-芴-9-基)甲氧基)羰基)(苄基)氨基)乙酸 | 141743-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 2-((((9H-芴-9-基)甲氧基)羰基)(苄基)氨基)乙酸
• 中文别名: Fmoc-N-苄基甘氨酸
• 英文名称: N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-benzylglycine
• 英文别名: 2-[benzyl-(9H-fluoren-9-ylmethoxycarbonyl)amino]acetic acid；2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(benzyl)amino)acetic acid；2-[benzyl(9H-fluoren-9-ylmethoxycarbonyl)amino]acetic acid
• CAS: 141743-13-7
• 化学式: C₂₄H₂₁NO₄
• 分子量: 387.435
• InChiKey: IZXYZVSMRGDEOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  604.0±44.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  适宜温度：2-8℃，需保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc,bzl-gly-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,bzl-gly-oh
CAS number: 141743-13-7

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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: C24H21NO4
Molecular weight: 387.4

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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：

  2-((((9H-芴-9-基)甲氧基)羰基)(苄基)氨基)乙酸 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (9H-fluoren-9-yl)methyl benzyl(2-chloro-2-oxoethyl)carbamate
  参考文献：
  名称：

  所罗门酰胺天然产物大环核心的连续扩环策略

  摘要：

  基于应用三个连续扩环反应的合成策略已用于合成所罗门酰胺天然产物大环核心的类似物。从一个简单、容易获得的四氢咔唑开始，氧化环扩展之后是两个进一步的 3 和 4 原子环扩展反应，从而能够将氨基酸和羟基酸衍生的线性片段插入 15 至 17 元环-扩大大周期产品。

  DOI：

  10.1055/a-1932-9717
• 作为产物：
  描述：

  N-苄基甘氨酸乙酯 在 盐酸 、 sodium hydroxide 、 TEA 、 水 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 2-((((9H-芴-9-基)甲氧基)羰基)(苄基)氨基)乙酸
  参考文献：
  名称：

  Solid-Phase Syntheses of Peptoids using Fmoc-ProtectedN-Substituted Glycines: The Synthesis of (Retro)Peptoids of Leu-Enkephalin and Substance P

  摘要：

  A particularly interesting class of oligomeric peptidomimetics is formed by the peptoids, which consist of N-substituted glycine residues. A solid-phase synthesis method for peptoids is presented in which these residues are introduced using their Fmoc derivatives. This "monomer" method allowed the monitored synthesis of relatively large quantities of pure peptoids as well as the translation of, in principle, any peptide into the corresponding peptoid. The required Fmoc-substituted glycines were accessible by convenient synthesis, and a number of monomers including those containing side chains with functional groups have been synthesized. The use of Fmoc monomers also allowed implementation of a solid-phase synthesis protocol on a commercial peptide synthesizer. The method was exemplified by the solid-phase syntheses of the (retro)peptoids of Leu-enkephalin and substance P. Mass spectrometric studies of (retro)peptoids were essential for their characterization, and the presence of the B- and Y "- type ions allows sequence analysis. Substance P (retro)-peptoids were biologically active. HPLC analysis showed an increased hydrophobicity, and pepsin treatment resulted in greatly reduced degradation compared with the corresponding peptide.

  DOI：

  10.1002/(sici)1521-3765(19980807)4:8<1570::aid-chem1570>3.0.co;2-2

文献信息

• An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes
  作者：Yutong Lin、Lara R. Malins

  DOI：10.1021/jacs.1c05718

  日期：2021.8.4

  amides are accessed in an efficient and epimerization-free approach by pairing an electrochemical oxidative decarboxylation with a tandem hydrolysis/reduction pathway. Resembling Nature’s dual enzymatic approach to bioactive primary α-amides, this method delivers secondary and tertiary amides bearing high-value functional motifs, including isotope labels and handles for bioconjugation. The protocol leverages

  通过将电化学氧化脱羧与串联水解/还原途径配对，以一种有效且无差向异构化的方法获得设计者 C 末端肽酰胺。类似于 Nature 对生物活性伯 α-酰胺的双重酶促方法，该方法提供具有高价值功能基序的仲和叔酰胺，包括同位素标记和用于生物偶联的手柄。该协议利用了 C 末端羧酸盐的固有反应性，与绝大多数蛋白质功能组兼容，并且在没有差向异构化的情况下进行，从而解决了与传统基于耦合的方法相关的主要限制。该方法的实用性通过合成天然产物 acidiphilamide A来举例说明关键的非对映选择性还原，以及生物活性肽和相关类似物，包括抗 HIV 先导肽和重磅炸弹癌症治疗剂亮丙瑞林。
• Tuning conformation and properties of peptidomimetic backbones through dual <i>N</i>/<i>C</i>_α-substitution
  作者：R. Kaminker、I. Kaminker、W. R. Gutekunst、Y. Luo、S. Lee、J. Niu、S. Han、C. J. Hawker

  DOI：10.1039/c8cc01356j

  日期：——

  Conformational space of peptides can be fine-tuned via chemical modifications of the backbone.

  肽的构象空间可以通过对骨架的化学修饰进行微调。
• Peptide/Peptoid Hybrid Oligomers: The Influence of Hydrophobicity and Relative Side-Chain Length on Antibacterial Activity and Cell Selectivity
  作者：Nicki Frederiksen、Paul R. Hansen、Fredrik Björkling、Henrik Franzyk

  DOI：10.3390/molecules24244429

  日期：——

  relationships within a subclass of oligomers displaying variation of three structural features: (i) cationic side-chain length, (ii) hydrophobic side-chain length, and (iii) type of residue that is of a flexible peptoid nature. Increased side-chain length of cationic residues led to reduced hydrophobicity till the side chains became more extended than the aromatic/hydrophobic side chains, at which point

  先前对肽/拟肽杂交体的优化研究通常包括比较显示不同寡聚体长度和不同侧链的结构相关类似物。目前的工作涉及系统构建的一系列 16 个密切相关的 12 聚体低聚物，具有交替的阳离子/疏水设计，代表了广泛的疏水性和相对侧链长度的差异。目的是探索和合理化显示三个结构特征变化的低聚物亚类内的结构 - 活性关系：（i）阳离子侧链长度，（ii）疏水侧链长度，以及（iii）残基类型具有灵活的拟肽性质。阳离子残基侧链长度的增加导致疏水性降低，直到侧链变得比芳香族/疏水性侧链更长，此时疏水性略有增加。抗菌活性评估表明，具有最低疏水性的类似物对大肠杆菌的活性降低，而具有最短阳离子侧链的低聚物对铜绿假单胞菌最有效。因此，与铜绿假单胞菌的膜破坏相互作用似乎是由低聚物的疏水表面（由保护阳离子侧链的芳族基团组成）促进的。具有短阳离子侧链的肽模拟物表现出增加的溶血特性以及降低 HepG2（肝母细胞瘤 G2 细胞系）细胞活力。
• Synthesis of Cyclic Peptide Mimetics by the Successive Ring Expansion of Lactams
  作者：Thomas C. Stephens、Mahendar Lodi、Andrew M. Steer、Yun Lin、Matthew T. Gill、William P. Unsworth

  DOI：10.1002/chem.201703316

  日期：2017.9.27

  successive ring‐expansion protocol is reported that enables the controlled insertion of natural and non‐natural amino acid fragments into lactams. Amino acids can be installed into macrocycles via an operationally simple and scalable iterative procedure, without the need for high dilution. This method is expected to be of broad utility, especially for the synthesis of medicinally important cyclic peptide

  据报道，有连续的扩环方案可以将天然和非天然氨基酸片段控制插入内酰胺中。可以通过操作简单且可扩展的迭代程序将氨基酸安装到大环化合物中，而无需进行高稀释。预期该方法具有广泛的用途，特别是对于合成具有医学重要性的环状肽模拟物而言。
• PEPTOID-BASED CHELATING LIGANDS FOR SELECTIVE METAL CHELATION
  申请人：Triad National Security, LLC

  公开号：US20200109173A1

  公开（公告）日：2020-04-09

  The present disclosure provides peptoid-based chelating ligands, corresponding cyclic peptoids, and methods of making thereof. Functional groups may be tailored for high metal binding affinity and selectivity. The side chains of a cyclic peptoid according to the present disclosure may be selected based on, for example, high affinity for actinide or other metal ions, selectivity for actinide or other metal ions, the ability to recover a metal once it is bound to the peptoid, and whether the overall peptoid should be hydrophobic or hydrophilic. Unlike siderophores, peptoid-based chelating ligands of the present disclosure are not readily hydrolyzed under physiological conditions. Therefore, peptoid-based chelating ligands may be, for example, used to treat actinide (e.g., iron and lead) poisoning in vivo. Moreover, peptoid-based chelating ligands of the present disclosure may be used for medical imaging, chelation therapy, drug delivery, and separation technologies, for example.

  本公开提供基于肽酰胺的螯合配体、相应的环状肽酰胺及其制备方法。功能基团可以根据高金属结合亲和力和选择性进行定制。根据本公开的环状肽酰胺的侧链可以根据，例如，对锕系元素或其他金属离子的高亲和力、对锕系元素或其他金属离子的选择性、一旦金属与肽酰胺结合后是否能够回收金属，以及整体肽酰胺是疏水性还是亲水性来进行选择。与铁载体不同，本公开的基于肽酰胺的螯合配体在生理条件下不容易水解。因此，基于肽酰胺的螯合配体可以用于治疗体内的锕系元素（例如铁和铅）中毒。此外，本公开的基于肽酰胺的螯合配体可以用于医学成像、螯合疗法、药物输送和分离技术等领域。