N-乙酰基-L-丙氨酰-L-丙氨酰-L-丙氨酸 | 19245-85-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 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: N-乙酰基-L-丙氨酰-L-丙氨酰-L-丙氨酸
• 中文别名: N-乙酰-丙氨酰-丙氨酰-丙氨酸
• 英文名称: Ac-Ala₃OH
• 英文别名: Ac-Ala-Ala-Ala-OH；Ac-(Ala)3-OH；Ac-AAA；Ac-Ala-Ala-Ala；Acetyltrialanine；(2S)-2-[[(2S)-2-[[(2S)-2-acetamidopropanoyl]amino]propanoyl]amino]propanoic acid
• CAS: 19245-85-3
• 化学式: C₁₁H₁₉N₃O₅
• 分子量: 273.289
• InChiKey: DRYOODAJROGPQO-ACZMJKKPSA-N

物化性质

• 熔点：
  248 °C
• 沸点：
  416.31°C (rough estimate)
• 密度：
  1.2363 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2924199090
• 储存条件：
  存储于-20°C阴凉干燥处。

SDS

Name:	n-Acetyl-l-alanyl-l-alanyl-l-alanine Material Safety Data Sheet
Synonym:
CAS:	19245-85-3

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

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
19245-85-3	N-acetyl-l-alanyl-l-alanyl-l-alanine	100	242-912-3

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. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation. Use with adequate ventilation.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.) Keep containers tightly closed.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 19245-85-3: 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: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 248 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: C11H19N3O5
Molecular Weight: 273.28

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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:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 19245-85-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-acetyl-l-alanyl-l-alanyl-l-alanine - 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# 19245-85-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 19245-85-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 19245-85-3 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

Acetyltrialanine binds to two sites on the complex formed by Tb³⁺ and pancreatic elastase.

反应信息

• 作为反应物：
  描述：

  N-乙酰基-L-丙氨酰-L-丙氨酰-L-丙氨酸 在 N,N-二异丙基乙胺 、 氯磷酸二苯酯 作用下， 以 氘代乙腈 为溶剂， 生成 (2S)-2-acetamido-N-[(1S)-1-[(4S)-4-methyl-5-oxo-4H-1,3-oxazol-2-yl]ethyl]propanamide
  参考文献：
  名称：

  Activation of the Carboxy Terminus of a Peptide for Carboxy-Terminal Sequencing

  摘要：

  Previously, we reported [Anal. Biochem. 1992, 206, 344-352] a new method of sequencing proteins from the carboxy terminus (C-terminus). The carboxyl group at the C-terminus is activated and derivatized into a thiohydantoin (TH). We reported that, by alkylating the TH formed at the C-terminus, the TH is converted into a readily displaced leaving group. Reaction with {NCS}(-) under acidic conditions cleaves the alkylated thiohydantoin (ATH) and derivatizes the freshly exposed C-terminus into a new proteinyl-TH. The efficiency of the initial activation of the carboxy group at the C-terminus is critical to the initial yield of the first ATH residue. In order to directly observe the intermediates that form during activation of the C-terminus, a model tripeptide, acetylalanine-alanine-alanine-OH (Ac-Ala-Ala-Ala-OH) was subjected to the reagents used to form the peptidyl-TH, Ac-Ala-Ala-Ala-TH. The reaction was monitored by nuclear magnetic resonance spectroscopy. An oxazolone was observed to form immediately at the C-terminus during the reaction with diphenyl chlorophosphate (DPCP), tetraphenyl pyrophosphate (TPPP), or tetramethylchlorouronium chloride (TMU-Cl). The oxazolone was observed to react with an excess of the carboxy group-activating reagents while under basic conditions. Diketopiperazine formation at the C-terminus was also observed. These side reactions prevent or retard the reaction of (NCS)- to form a peptidyl-TH and correlate with a reduced initial yield observed during automated C-terminal protein sequencing. The carboxylic acid-reactive reagents react with the side-chain carboxylic acid groups of aspartic and glutamic acid residues as well as the C-terminus. We found that the sidechain carboxylic acid groups in a protein could be selectively amidated in the presence of the proteinyl-oxazolone at the C-terminus.

  DOI：

  10.1021/jo00113a042
• 作为产物：
  描述：

  Phosphoric acid 2-[(S)-1-((S)-2-acetylamino-propionylamino)-ethyl]-4-methyl-oxazol-5-yl ester diphenyl ester 在 重水 、 三氟乙酸 作用下， 以 氘代乙腈 为溶剂， 反应 0.5h， 生成 N-乙酰基-L-丙氨酰-L-丙氨酰-L-丙氨酸
  参考文献：
  名称：

  Activation of the Carboxy Terminus of a Peptide for Carboxy-Terminal Sequencing

  摘要：

  Previously, we reported [Anal. Biochem. 1992, 206, 344-352] a new method of sequencing proteins from the carboxy terminus (C-terminus). The carboxyl group at the C-terminus is activated and derivatized into a thiohydantoin (TH). We reported that, by alkylating the TH formed at the C-terminus, the TH is converted into a readily displaced leaving group. Reaction with {NCS}(-) under acidic conditions cleaves the alkylated thiohydantoin (ATH) and derivatizes the freshly exposed C-terminus into a new proteinyl-TH. The efficiency of the initial activation of the carboxy group at the C-terminus is critical to the initial yield of the first ATH residue. In order to directly observe the intermediates that form during activation of the C-terminus, a model tripeptide, acetylalanine-alanine-alanine-OH (Ac-Ala-Ala-Ala-OH) was subjected to the reagents used to form the peptidyl-TH, Ac-Ala-Ala-Ala-TH. The reaction was monitored by nuclear magnetic resonance spectroscopy. An oxazolone was observed to form immediately at the C-terminus during the reaction with diphenyl chlorophosphate (DPCP), tetraphenyl pyrophosphate (TPPP), or tetramethylchlorouronium chloride (TMU-Cl). The oxazolone was observed to react with an excess of the carboxy group-activating reagents while under basic conditions. Diketopiperazine formation at the C-terminus was also observed. These side reactions prevent or retard the reaction of (NCS)- to form a peptidyl-TH and correlate with a reduced initial yield observed during automated C-terminal protein sequencing. The carboxylic acid-reactive reagents react with the side-chain carboxylic acid groups of aspartic and glutamic acid residues as well as the C-terminus. We found that the sidechain carboxylic acid groups in a protein could be selectively amidated in the presence of the proteinyl-oxazolone at the C-terminus.

  DOI：

  10.1021/jo00113a042

文献信息

• Controlled Formation of Peptide Bonds in the Gas Phase
  作者：Sunyoung Lee、Stephen J. Valentine、James P. Reilly、David E. Clemmer

  DOI：10.1021/ja205471n

  日期：2011.10.12

  radiation) of proton-bound peptide complexes leads to water elimination and the formation of longer amino acid chains. Thus, it appears that proton-bound dimers are long-lived intermediates along the pathway to peptide formation. Product specificity can be controlled by selection of specific complexes and the incorporation of blocking groups at the N- or C-termini. The product peptide sequences are confirmed

  质子结合肽复合物的光激发（使用 157 nm 真空紫外线辐射）导致水消除和更长的氨基酸链的形成。因此，质子结合的二聚体似乎是肽形成途径中的长寿命中间体。产品特异性可以通过选择特定的复合物和在 N 或 C 端加入封闭基团来控制。使用碰撞诱导解离确认产物肽序列。
• Control of nano-micrometric twist and helical ribbon formation with gemini–oligoalanine via interpeptidic β-sheet structure formation
  作者：Aurélie Brizard、Roni Kiagus Ahmad、Reiko Oda

  DOI：10.1039/b700959c

  日期：——

  Confinement of anionic oligo-alanine peptides at the surfaces of cationic membrane by ionic interaction can induce their secondary structure formation; such organized peptides reciprocally transfer their chirality to membranes with non-chiral amphiphiles and their supramolecular chiral structures can be tuned both by peptides and amphiphiles structures.

  阴离子低聚丙氨酸肽通过离子相互作用被限制在阳离子膜的表面，可诱导其二级结构的形成；这种有组织的肽可将其手性相互转移到带有非手性两性化合物的膜上，其超分子手性结构可通过肽和两性化合物的结构进行调整。
• The Synthesis of a Prodrug of Doxorubicin Designed to Provide Reduced Systemic Toxicity and Greater Target Efficacy
  作者：Victor M. Garsky、Patricia K. Lumma、Dong-Mei Feng、Jenny Wai、Harri G. Ramjit、Mohinder K. Sardana、Allen Oliff、Raymond E. Jones、Deborah DeFeo-Jones、Roger M. Freidinger

  DOI：10.1021/jm0101996

  日期：2001.11.1

  have been found to correlate well with the number of malignant prostate cells. The use of a prodrug which is cleaved by the enzyme PSA in the prostate should in principle produce high localized concentrations of the cytotoxic agent at the tumor site while limiting systemic exposure to the active drug. Cleavage maps following PSA treatment of human semenogelin were constructed. Systematic modification

  阿霉素（Dox）可在前列腺癌中提供一定的稳定作用；然而，由于全身毒性，主要是心脏毒性和免疫抑制，其使用受到限制。设计用于允许肿瘤选择性激活的阿霉素前药的施用将减少对活性药物的全身全身暴露，从而增加治疗指数。前列腺特异抗原（PSA）是具有胰凝乳蛋白酶样活性的丝氨酸蛋白酶，是激肽释放酶基因家族的成员。PSA凭借其裂解精液蛋白精囊蛋白I和II的能力，被认为是精液的液化。已经发现血清PSA水平与恶性前列腺细胞的数量很好地相关。原则上，在前列腺中使用被PSA酶裂解的前药应在肿瘤部位产生高浓度的细胞毒剂，同时限制全身暴露于活性药物。PSA处理人精液明胶后的切割图被构建。在主要切割位点侧翼的氨基酸残基的系统修饰导致合成了一系列短肽，这些短肽可被PSA有效水解。随后将选定的肽与阿霉素偶联提供了一系列阿霉素-肽缀合物，其在体外和体内被评估为分泌PSA的肿瘤细胞的靶向前药。从这些研究中，我们选择27岁的Glu
• [EN] PROTEASE DEFICIENT BACTERIAL HOSTS
  申请人：THE GENERAL HOSPITAL CORPORATION

  公开号：WO1991017247A1

  公开（公告）日：1991-11-14

  (EN) $i(E. coli) mutants which are capable of expressing cloned proteins in a highly stable manner are described.(FR) Mutants de $i(E. coli) capables d'exprimer des protéines clonées de manière hautement stable.

  描述了能够以高度稳定方式表达克隆蛋白质的 $i(E. coli) 变种。 $i(E. coli)变种能够以高度稳定方式表达克隆蛋白质。
• Jahreis, Guenther; Smalla, Kornelia; Fittkau, Siegfried, Journal fur praktische Chemie (Leipzig 1954), 1984, vol. 326, # 1, p. 41 - 47
  作者：Jahreis, Guenther、Smalla, Kornelia、Fittkau, Siegfried

  DOI：——

  日期：——