N-乙酰基-L-酪氨酸胺 | 1948-71-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酪氨酸类衍生物
• 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-乙酰基-L-酪氨酸胺
• 中文别名: 乙酰酪胺酰胺；N-乙酰基-L-酪氨酰胺；N-乙酰-L酪氨酰胺；乙酰-L-酪氨酰胺
• 英文名称: N-acetyl-L-tryrosinamide
• 英文别名: N^α-acetyl-L-tyrosine amide；N_α-acetyl-L-tyrosinamide；N-α-acetyl-L-tyrosinamide；N-acetyl L-tyrosine amide；N-acetyl-L-tyrosine amide；N-acetyl tyrosine amide；N-Acetyl-L-tyrosinamide；(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamide
• CAS: 1948-71-6
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: RJNKBEQRBIJDNM-JTQLQIEISA-N

物化性质

• 熔点：
  223-225 °C(lit.)
• 沸点：
  363.42°C (rough estimate)
• 密度：
  1.253
• 溶解度：
  可溶于DMSO（少量）、甲醇（少量）、水（少量）
• 稳定性/保质期：
  在常温常压下保持稳定，但应避免与不相容的材料接触。与强氧化剂可能发生反应。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  密封储存，存放在阴凉干燥处，并将冷藏温度控制在4°C。

SDS

Name:	n-Acetyl-l-tyrosinamide Material Safety Data Sheet
Synonym:
CAS:	1948-71-6

Section 1 - Chemical Product MSDS Name:n-Acetyl-l-tyrosinamide Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1948-71-6	N-acetyl-l-tyrosinamide	100	217-756-4

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Dust may cause mechanical irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1948-71-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 223.00 - 225.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H14N2O3
Molecular Weight: 222.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1948-71-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-acetyl-l-tyrosinamide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1948-71-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1948-71-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1948-71-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

制备方法

生化研究，测定胰凝乳蛋白酶的底物。

用途简介 用途

生化研究，测定胰凝乳蛋白酶的底物。

反应信息

• 作为反应物：
  描述：

  N-乙酰基-L-酪氨酸胺 在 potassium phosphate buffer 作用下， 反应 1.0h， 生成 N-乙酰-L-酪氨酸
  参考文献：
  名称：

  Nishida, Yutaka; Nabe, Koichi; Yamada, Shigeki, Agricultural and Biological Chemistry, 1983, vol. 47, # 7, p. 1667 - 1668

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙酰-L-酪氨酸 在 4-二甲氨基吡啶 、 氯化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-乙酰基-L-酪氨酸胺
  参考文献：
  名称：

  使用双氰基芳烃光诱导电子转移促进苯丙氨酸和酪氨酸衍生物的脱苄基作用

  摘要：

  苯丙氨酸和酪氨酸衍生物与双氰基芳烃的光诱导脱苄基反应通过产生自由基阳离子提供了甘氨酸衍生物。尽管底物范围有限，但在N端带有氨基甲酸酯（无芳族基团）和C端带有酰胺的苯丙氨酸和酪氨酸衍生物的自由基阳离子可通过以下方式促进苄基位置的C–C键断裂：光诱导的电子转移。重要的是要了解涉及电子转移的酶中苯丙氨酸和酪氨酸的自由基阳离子的化学行为。

  DOI：

  10.1016/j.tet.2017.11.021

文献信息

• Direct conversion of phenols into primary anilines with hydrazine catalyzed by palladium
  作者：Zihang Qiu、Leiyang Lv、Jianbin Li、Chen-Chen Li、Chao-Jun Li

  DOI：10.1039/c9sc00595a

  日期：——

  Primary anilines are essential building blocks to synthesize various pharmaceuticals, agrochemicals, pigments, electronic materials, and others. To date, the syntheses of primary anilines mostly rely on the reduction of nitroarenes or the transition-metal-catalyzed Ullmann, Buchwald–Hartwig and Chan–Lam cross-coupling reactions with ammonia, in which non-renewable petroleum-based chemicals are typically

  伯苯胺是合成各种药物、农用化学品、颜料、电子材料等的重要组成部分。迄今为止，伯苯胺的合成主要依靠硝基芳烃的还原或过渡金属催化的Ullmann、Buchwald-Hartwig和Chan-Lam与氨的交叉偶联反应，其中通常使用不可再生的石油基化学品作为原料通过多步合成。一个长期存在的科学挑战是直接从可再生资源合成各种初级苯胺。在此，我们报告了一种通用方法，以廉价且广泛使用的肼作为胺和氢化物源，以简单的 Pd/C 作为催化剂，将多种酚直接转化为相应的伯苯胺。
• Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent
  作者：Tyler J. Wadzinski、Angela Steinauer、Liana Hie、Guillaume Pelletier、Alanna Schepartz、Scott J. Miller

  DOI：10.1038/s41557-018-0041-8

  日期：2018.6

  Glycosylated natural products and synthetic glycopeptides represent a significant and growing source of biochemical probes and therapeutic agents. However, methods that enable the aqueous glycosylation of endogenous amino acid functionality in peptides without the use of protecting groups are scarce. Here, we report a transformation that facilitates the efficient aqueous O-glycosylation of phenolic

  糖基化的天然产物和合成的糖肽代表了生化探针和治疗剂的重要且不断增长的来源。然而，缺少能够在不使用保护基的情况下使肽中的内源氨基酸官能团进行水性糖基化的方法。在这里，我们报道了一种转化，该转化促进了在广泛的小分子，未保护的酪氨酸和嵌入一系列复杂，完全未保护的肽中的酪氨酸残基的酚官能团的有效O-糖基化水溶液。该转化使用糖基氟化物供体，并由Ca（OH）2促进，取决于糖基供体的立体化学，在室温下在水中迅速进行，并具有良好的收率和选择性形成独特的异头物产物。观察到高官能团耐受性，并且在几乎所有蛋白原性氨基酸的所有侧链均存在的情况下，Cys例外，酚糖基化选择性发生。该方法为水中的O-芳基糖苷和Tyr- O-糖基化肽的无保护基的合成提供了高度选择性，有效且操作简单的方法。
• N-Ethyl-5-phenylisoxazolium 3'-sulfonate (Woodward's Reagent K) as a reagent for nucleophilic side chains of proteins
  作者：Kathryn. Llamas、Mark. Owens、Robert L. Blakeley、Burt. Zerner

  DOI：10.1021/ja00278a030

  日期：1986.9

  N-Ethyl-5-phenylisoxazolium-3′-sulfonate (1) is converted to the corresponding keto ketenimine [ArC(O)CH=C=NEt, 2] in a hydroxide-promoted reaction with k- OH = 6.64 × 10 5 M -1 s -1 at 25°C. The rate law for spontaneous hydration of 2 to form N-ethyl-3-oxo-3-(3-sulfonatophenyl)propanamide is k sp obsd = k H+[H +] + k w + k -OH[ -OH], where k H+ = 442 M -1 s -1 k w = 0.0116 s -1, and k- OH = 254 M

  N-乙基-5-苯基异恶唑鎓-3'-磺酸盐 (1) 在与 k-OH = 6.64 × 10 5 的氢氧化物促进反应中转化为相应的酮烯酮亚胺 [ArC(O)CH=C=NEt, 2] M -1 s -1 在 25°C。2 自发水合形成 N-乙基-3-氧代-3-(3-磺基苯基)丙酰胺的速率定律为 k sp obsd = k H+[H +] + kw + k -OH[ -OH]，其中 k H+ = 442 M -1 s -1 kw = 0.0116 s -1，并且 k-OH = 254 M -1 s -1 在 25°C (μ = 0.1)。在醋酸盐缓冲液中，k obsd = k sp obsd + k AcO[AcO -] + k AcOH[AcOH]，其中 k AcO- = 0.245 M -1 s -1 和 k AcOH = 2.33 M -1 s -1。这两个催化术语都导致烯醇酯[3-乙酰氧基
• Acceptor-Controlled Transfer Dehydration of Amides to Nitriles
  作者：Hiroyuki Okabe、Asuka Naraoka、Takahiro Isogawa、Shunsuke Oishi、Hiroshi Naka

  DOI：10.1021/acs.orglett.9b01657

  日期：2019.6.21

  dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired

  通过使用二氯乙腈作为水受体，在温和的水性条件下钯催化的伯酰胺脱水有效地进行为腈。设计该转移脱水催化的关键是确定一种有效的水受体二氯乙腈，该水受体在Pd催化剂的帮助下优先于酰胺而不是其他极性官能团反应，并使所需的反应体系趋于能动，从而驱动脱水。
• <i>S</i>-Acyl-2-Thioethyl Aryl Phosphotriester Derivatives of AZT:  Synthesis, Antiviral Activity, and Stability Study
  作者：Suzanne Peyrottes、Gaëlle Coussot、Isabelle Lefebvre、Jean-Louis Imbach、Gilles Gosselin、Anne-Marie Aubertin、Christian Périgaud

  DOI：10.1021/jm021016y

  日期：2003.2.1

  The synthesis, antiviral activity, and stability study of phosphotriester derivatives of 3'-azido-2',3'-dideoxythymidine (AZT) bearing modified l-tyrosinyl residues are reported. These compounds were obtained via phosphoramidite (P(III)) chemistry from the appropriate aryl precursors. All the derivatives were evaluated for their in vitro anti-HIV activity, and they appeared to be potent inhibitors

  报道了带有修饰的1-酪氨酸残基的3'-叠氮基2'，3'-二脱氧胸苷（AZT）的磷酸三酯衍生物的合成，抗病毒活性和稳定性研究。这些化合物是通过亚磷酰胺（P（III））化学方法从适当的芳基前体获得的。评估了所有衍生物的体外抗HIV活性，在各种细胞培养实验中，它们似乎都是HIV-1复制的有效抑制剂，EC（50）值介于微摩尔和纳摩尔之间，尤其是在胸苷激酶中缺陷（TK（-））细胞，显示其充当单核苷酸前药的能力。这些混合的单核苷芳基磷酸三酯的拟议分解过程依次涉及酯酶和磷酸二酯酶的水解。

表征谱图