4-叠氮基-l-苯丙氨酸 | 33173-53-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-叠氮基-l-苯丙氨酸
• 中文别名: 4-叠氮基-L-苯丙氨酸
• 英文名称: 4-azido-L-phenylalanine
• 英文别名: p-azido-L-phenylalanine；(2S)-2-azaniumyl-3-(4-azidophenyl)propanoate
• CAS: 33173-53-4
• 化学式: C₉H₁₀N₄O₂
• 分子量: 206.204
• InChiKey: NEMHIKRLROONTL-QMMMGPOBSA-N

物化性质

• 溶解度：
  水：6.2 mg/mL（30.07 mM；超声并用 HCl 将 pH 调节至 6）；DMSO：6 mg/mL（29.10 mM；超声并用 HCl 将 pH 调节至 6）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2929909090
• 储存条件：
  | 2-8℃ |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Azido-l-phenylalanine
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: 4-Azido-l-phenylalanine
CAS number: 33173-53-4

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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: C9H10N4O2
Molecular weight: 206.2

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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

制备方法与用途

生物活性

4-氨基-L-苯丙氨酸是一种非天然氨基酸，能够报告局部蛋白质环境。

体外研究

在细胞自由蛋白质合成（CFPS）方法中，含有4-氨基-L-苯丙氨酸或p-丙氧基-L-苯丙氨酸（pPaF）的0.9-1.7 mg/mL修饰可溶性超级折叠绿色荧光蛋白（sfGFP）会在CFPS溶液中累积。

用途

一种非天然氨基酸衍生物。

反应信息

• 作为反应物：
  描述：

  4-叠氮基-l-苯丙氨酸 在 三甲基氯硅烷 、 copper diacetate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 14.17h， 生成 3-[4-(5-formyl-thiazol-2-yl)-phenyl]-2-(2,4,6-trimethyl-benzoylamino)-propionic acid methyl ester
  参考文献：
  名称：

  WO2007/131764

  摘要：

  公开号：
• 作为产物：
  描述：

  4-iodo-L-phenylalanine 在 三乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 硫酸 、 水 、 乙酸乙酯 为溶剂， 反应 42.0h， 生成 4-叠氮基-l-苯丙氨酸
  参考文献：
  名称：

  4-叠氮基-1-苯丙氨酸的合成和爆炸危险

  摘要：

  描述了一种从1-苯丙氨酸开始的可靠，可扩展，成本有效且无色谱的4-叠氮基-1-苯丙氨酸的合成方法。对合成安全性的研究表明，类似Ullman的Cu（I）催化的叠氮化步骤并不构成重大风险。但是，分离出的4-叠氮基-1-苯丙氨酸产物具有以前未记录的爆炸特性。

  DOI：

  10.1021/acs.joc.8b00270

文献信息

• TUBULYSIN ANALOGS AND METHODS OF MAKING AND USE
  申请人：Bristol-Myers Squibb Company

  公开号：US20160130299A1

  公开（公告）日：2016-05-12

  Tubulysin analogs of the formula (I) where R 1 , R 2 R 3 , R 4 , R 5 , R 6 , R 7 , and Y are as defined herein, are anti-mitotic agents that can be used in the treatment of cancer, especially when conjugated to a targeting moiety.

  管素类似物公式(I)，其中R1、R2、R3、R4、R5、R6、R7和Y如本文所述定义，是一种抗有丝分裂剂，可用于癌症治疗，特别是在与靶向部分结合时。
• Modified Human Apolipoprotein A-1 and Their Uses
  申请人：Knudsen Nick

  公开号：US20110178029A1

  公开（公告）日：2011-07-21

  Modified human apolipoprotein A-I polypeptides and uses thereof are provided.

  提供了改良的人类载脂蛋白A-I多肽及其用途。
• MODIFIED RELAXIN POLYPEPTIDES AND THEIR USES
  申请人：KRAYNOV Vadim

  公开号：US20120046229A1

  公开（公告）日：2012-02-23

  Modified relaxin polypeptides and their uses thereof are provided

  修改后的弛缓素多肽及其用途
• Modified Leptin Polypeptides and Their Uses
  申请人：Kraynov Vadim

  公开号：US20120149636A1

  公开（公告）日：2012-06-14

  Modified human leptin polypeptides and uses thereof are provided.

  提供了改良的人类瘦素多肽及其用途。
• [EN] MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS<br/>[FR] CATALYSEURS À BASE DE MYOGLOBINE POUR RÉACTIONS DE TRANSFERT DE CARBÈNE
  申请人：UNIV ROCHESTER

  公开号：WO2016086015A1

  公开（公告）日：2016-06-02

  Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).

  提供了一种方法来进行碳烯转移反应，如烯烃环丙烷化反应，碳烯杂原子-H插入反应（杂原子= N，S，Si），σ迁移重排反应和醛烯化反应，通过使用一种新型的基于肌红蛋白的生物催化剂，可以高效和选择性地进行。这些方法对于合成含有一个或多个新碳-碳或碳-杂原子（N，S或Si）键的各种有机化合物非常有用。这些方法可以应用于体外（即使用分离形式的生物催化剂）和体内（即在整个细胞系统中使用生物催化剂）进行这些转化。