N-氯乙酰基-L-色氨酸 | 64709-57-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 色氨酸类衍生物
• 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: N-氯乙酰基-L-色氨酸
• 中文别名: 氯乙酰基-L-色氨酸；氯乙酰-L-色氨酸
• 英文名称: N-(chloroacetyl)tryptophan
• 英文别名: N²-(chloroacetyl)-L-tryptophan；N-chloroacetyl-L-tryptophan；2-(2-chloroacetamido)-3-(1H-indol-3-yl)propanoic acid；2-chloracetyl tryptophan；N^α-chloroacetyl-L-tryptophan；N^α-Chloracetyl-L-tryptophan；(2S)-2-[(2-chloroacetyl)amino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 64709-57-5
• 化学式: C₁₃H₁₃ClN₂O₃
• mdl: MFCD00065977
• 分子量: 280.711
• InChiKey: PGTJUXHMJYBSBW-NSHDSACASA-N

物化性质

• 熔点：
  163 °C
• 沸点：
  610.2±55.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在指定条件下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 储存条件：
  存放在密封容器内，并置于阴凉、干燥处。建议在-20°C下保存。

SDS

Chloroacetyl-L-tryptophan
SAFETY DATA SHEET

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Section 1. IDENTIFICATION OF THE SUBSTANCE OR MIXTURE AND OF THE SUPPLIER
Product name: Chloroacetyl-L-tryptophan

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
Pictograms or hazard symbols
Signal word Warning
Hazard statement Causes skin irritation
Causes serious eye irritation
Precautionary statements
[Prevention] Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
[Response] IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): Chloroacetyl-L-tryptophan
Percent: >98.0%(T)
CAS Number: 64709-57-5
Chemical Formula: C13H13ClN2O3

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Chloroacetyl-L-tryptophan

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Section 4. FIRST AID MEASURES
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Keep container tightly closed. Store in a cool and dark place.
Storage conditions:
Store away from incompatible materials such as oxidizing agents.
Law is followed.
Packaging material:

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: crystal - powder
Color: Very pale yellow - Yellow
Odor: No data available
pH: No data available
Melting point/freezing point:163 °C
Boiling Point/Range: No data available
Chloroacetyl-L-tryptophan

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Flash Point: No data available
Explosive limits
Lower: No data available
No data available
Upper:
Density: No data available
No data available
Solubility:

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Section 10. STABILITY AND REACTIVITY
Stability: Stable under proper conditions.
Reactivity: No special reactivity has been reported.
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen chloride
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not Listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.
Chloroacetyl-L-tryptophan

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-氯乙酰基-L-色氨酸 以25%的产率得到
  参考文献：
  名称：

  MASCAL, MARK;MOODY, CHRISTOPHER J., J. CHEM. SOC. CHEM. COMMUN.,(1988) N 9, 587-588

  摘要：

  DOI：
• 作为产物：
  描述：

  氯乙酰氯 、 L-色氨酸 在 sodium hydroxide 作用下， 反应 0.17h， 以81%的产率得到N-氯乙酰基-L-色氨酸
  参考文献：
  名称：

  通过光环化反应合成3,4-桥联的吲哚。第1部分。卤代乙酰色氨酸衍生物的光环化

  摘要：

  虽然照射Ñ在photocyclisation的产量很低，以吲哚4-位由于竞争环化至C-2 -chloroacetyltryptophan结果，（二氯乙酰基）色氨酸衍生物的photocyclisation给出，添加亲核试剂的后在后处理，7-以高收率和反立体特异性取代取代的吡咯并苯甲恶唑啉。N-（三氯乙酰基）色氨酸衍生物也经过光环化反应，生成3,4-桥连吲哚。所述azocinoindoles的结构13，21，22和35，以及azepinoindole 15进行了X射线晶体学确认。在一种情况下，制备环烷基[ c，d ]吲哚可以通过吲哚-3-基链烷酸的α-氯酰胺的照射而形成。

  DOI：

  10.1039/p19920000797

文献信息

• PCl₃-mediated synthesis of green/cyan fluorescent protein chromophores using amino acids
  作者：Thokchom Prasanta Singh、Raja Shunmugam

  DOI：10.1039/c5nj03144c

  日期：——

  An efficient synthesis of green and cyan fluorescent protein chromophores froml-tyrosine andl-tryptophan using PCl₃has been successfully developed.

  一种高效合成绿色和青色荧光蛋白色素的方法已成功开发，使用的原料包括L-酪氨酸和L-色氨酸，并利用PCl3进行反应。
• Chemical and Ribosomal Synthesis of Topologically Controlled Bicyclic and Tricyclic Peptide Scaffolds Primed by Selenoether Formation
  作者：Yizhen Yin、Qianran Fei、Weidong Liu、Zhuoru Li、Hiroaki Suga、Chuanliu Wu

  DOI：10.1002/anie.201813827

  日期：2019.4

  chemical and ribosomal synthesis of topologically controlled bicyclic and tricyclic peptide scaffolds. Our strategy involves the combination of selenoether cyclization followed by disulfide or thioether cyclization, yielding desirable bicyclic and tricyclic peptides. This work thus lays the foundation for developing peptide libraries with controlled topology of multicyclic scaffolds for in vitro display

  双环和三环肽已成为开发蛋白结合剂和新疗法的有前途的候选者。但是，仍然需要大量方便，有效的策略来从完全未保护的肽生成拓扑控制的双环和三环肽支架，特别是对于那些适合于生物合成文库设计的策略。在这项工作中，我们报告了拓扑受控的双环和三环肽支架的可靠的化学和核糖体合成。我们的策略包括结合硒醚环化，然后进行二硫键或硫醚环化，从而产生所需的双环和三环肽。因此，这项工作为开发具有受控多环支架拓扑结构的肽库奠定了基础，以用于体外展示技术。
• [Gd(Try-TTDA)(H2O)]2−: A new MRI contrast agent for copper ion sensing
  作者：Dayananda Kasala、Tsung-Sheng Lin、Chiao-Yun Chen、Gin-Chung Liu、Chai-Lin Kao、Tian-Lu Cheng、Yun-Ming Wang

  DOI：10.1039/c1dt10033e

  日期：——

  In this study, we have developed two new L-tryptophan based contrast agents [Gd(Try-TTDA)(H2O)]2− and [Gd(Try-ac-DOTA)(H2O)]−. Upon addition of Cu(II) to [Gd(Try-TTDA)(H2O)]2−, significant increases in the relaxivity (r1) and hydration number of [Gd(Try-TTDA)(H2O)]2− were observed. However, it only induced a minute increase in the relaxivity (r1) in the case of [Gd(Try-ac-DOTA)(H2O)]−. Furthermore, the interaction of Cu(II) with the indole ring of Gd(III) complexes was explored by measuring the intrinsic fluorescence of the tryptophan of the Gd(III) complex. With the addition of one equivalent of Cu(II) to [Gd(Try-TTDA)(H2O)]2− the indole fluorescence was completely quenched. Moreover, the [Gd(Try-TTDA)(H2O)]2− complex shows excellent selectivity towards Cu(II) over other metal ions (Cu(II) > La(III) > Mg(II)). Importantly, the significant signal intensity (2073 ± 67) for in vitro MR imaging using [Gd(Try-TTDA)(H2O)]2− in the presence of Cu(II) implicates that this new smart contrast agent ([Gd(Try-TTDA)(H2O)]2−) can serve as a Cu(II) sensor for MR imaging.

  在这项研究中，我们开发了两种新的基于 L-色氨酸的造影剂[Gd(Try-TTDA)(H2O)]2â和[Gd(Try-ac-DOTA)(H2O)]â。在[Gd(Try-TTDA)(H2O)]2â中加入铜（II）后，[Gd(Try-TTDA)(H2O)]2â的弛豫度（r1）和水合数显著增加。然而，在[Gd(Try-ac-DOTA)(H2O)]â的情况下，它只引起了弛豫度（r1）的微小增加。此外，通过测量 Gd（III）络合物色氨酸的本征荧光，还探索了 Cu（II）与 Gd（III）络合物吲哚环的相互作用。在[Gd(Try-TTDA)(H2O)]2â中加入一个当量的 Cu(II)后，吲哚荧光被完全熄灭。此外，[Gd(Try-TTDA)(H2O)]2â 复合物对 Cu(II)的选择性优于其他金属离子（Cu(II) > La(III) > Mg(II)）。重要的是，使用[Gd(Try-TTDA)(H2O)]2â 在 Cu(II)存在下进行体外磁共振成像时，信号强度（2073 ± 67）显著，这表明这种新型智能造影剂（[Gd(Try-TTDA)(H2O)]2â）可用作磁共振成像的 Cu(II)传感器。
• Thiol compounds. II. Synthesis and antihypertensive activity of mercaptoacylamino acids.
  作者：MASAYUKI OYA、JUNZOH MATSUMOTO、HIDEO TAKASHINA、TOSHIO WATANABE、JUNICHI IWAO

  DOI：10.1248/cpb.29.940

  日期：——

  The synthesis and structure-activity relationship of a series of mercaptoacylamino acids are described. These compounds were tested for antihypertensive activity. When the compounds were screened as angiotensin I-converting enzyme inhibitors in vitro, N-(2-mercaptopropanoyl)-L-cysteine-a (7a) and N2-(2-mercaptopropanoyl)-L-tryptophan-a (20a) were found to be 10 and 20 times more active than tiopronin, respectively.

  本文描述了一系列巯基氨基酸的合成和结构-活性关系。对这些化合物进行了抗高血压活性测试。在将这些化合物作为血管紧张素 I 转换酶抑制剂进行体外筛选时，发现 N-（2-巯基丙酰基）-L-半胱氨酸-a（7a）和 N2-（2-巯基丙酰基）-L-色氨酸-a（20a）的活性分别是硫普罗宁的 10 倍和 20 倍。
• Macrocyclic Peptide, Method for Producing Same, and Screening Method Using Macrocyclic Peptide Library
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20160209421A1

  公开（公告）日：2016-07-21

  An object of the present invention is to provide a peptide excellent in resistance against metabolism, having a stable structure in vivo, and capable of penetrating a cell membrane and reaching in cells. The present invention provides a macrocyclic peptide having a macrocyclic structure comprised of four or more amino acids. At least two amino acids not adjacent to each other have a hydrophobic side chain and the hydrophobic side chains interact with each other inside the ring of the macrocyclic peptide in a hydrophilic environment.

  本发明的目的是提供一种具有抗代谢能力、在体内具有稳定结构、能够穿透细胞膜并进入细胞的肽。本发明提供一种具有四个或更多氨基酸构成的大环肽，其具有大环结构。至少有两个不相邻的氨基酸具有疏水侧链，并且这些疏水侧链在大环肽的环内在亲水环境中相互作用。

表征谱图