phosphoenolpyruvic acid monopotassium salt | 4265-07-0

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: phosphoenolpyruvic acid monopotassium salt
• 英文别名: potassium phosphoenolpyruvate；PEP；phosphoenolpyruvate monopotassium salt；PEP-K；monopotassium salt of phosphoenolpyruvate；monopotassium phosphoenol pyruvate；PEP-K; 2-(Phosphonooxy)-2-propenoic Acid Potassium Salt (1:1); Monopotassium Phosphoenolpyruvate; 2-hydroxy-Acrylic Acid Dihydrogen Phosphate Monopotassium Salt；potassium;2-phosphonooxyprop-2-enoate
• CAS: 4265-07-0
• 化学式: C₃H₄O₆P*K
• 分子量: 206.133
• InChiKey: SOSDSEAIODNVPX-UHFFFAOYSA-M

物化性质

• 熔点：
  175 °C (dec.)(lit.)
• 溶解度：
  甲醇（微溶）、水（微溶）
• 碰撞截面：
  163.7 Ų [M-H]-; 138.1 Ų [M+Na]+
• 稳定性/保质期：
  在常温常压下稳定且结晶，不水解。固体在4℃时亦保持稳定。它溶于水，并且其水溶液呈酸性。

计算性质

• 辛醇/水分配系数(LogP)：
  -3.93
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• TSCA：
  Yes
• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  本品应密封存放在0℃以下的干燥环境中保存。

SDS

Name:	Phosphoenolpyruvic Acid Monopotassium Salt 99% Material Safety Data Sheet
Synonym:	PEP
CAS:	4265-07-0

Section 1 - Chemical Product MSDS Name:Phosphoenolpyruvic Acid Monopotassium Salt 99% Material Safety Data Sheet
Synonym:PEP

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4265-07-0	Phosphoenolpyruvic Acid, Monopotassium	99%	224-247-0

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:
May cause eye 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.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. 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. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 4265-07-0: 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 minimize contact with skin.
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: 175.00 - 179.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C3H4O6PK
Molecular Weight: 206.13

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4265-07-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Phosphoenolpyruvic Acid, Monopotassium Salt - 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.
WGK (Water Danger/Protection)
CAS# 4265-07-0: 1
Canada
CAS# 4265-07-0 is listed on Canada's NDSL List.
CAS# 4265-07-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4265-07-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性 磷戊糖酸单钾盐（磷酸烯醇式丙酮酸单钾盐，化学名：Potassium 1-carboxyvinyl hydrogenphosphate）是一种内源性代谢产物。

用途 生化研究中的一种重要底物，广泛用于许多激酶反应。

反应信息

• 作为反应物：
  描述：

  phosphoenolpyruvic acid monopotassium salt 在 dipotassium hydrogenphosphate 、 磷酸 、 Alkaline phosphatase EC 3.1.3.1 作用下， 以 水 为溶剂， 反应 0.37h， 生成 丙酮酸
  参考文献：
  名称：

  腺苷3',5'-(环)磷酸(aq)和磷酸烯醇式丙酮酸(aq)水解反应的热力学；3',5'-(环状)磷酸酯(aq)和磷酸烯醇式丙酮酸(aq)的标准摩尔形成特性

  摘要：

  摘要 已经测量了生化反应 {cAMP(aq) + H2O(l)=AMP(aq)} 和 {PEP(aq) + H2O(l)=丙酮酸盐(aq) + 磷酸盐的摩尔量热焓变 ΔrHm(cal) (aq)}。该反应分别由磷酸二酯酶 3',5'-环核苷酸和碱性磷酸酶催化。通过使用化学平衡模型来分析结果以获得各个参考反应{cAMP-(aq) + H2O(l)=HAMP-(aq)}和{PEP3-(aq)的标准摩尔反应焓值ΔrHm∘ ) + H2O(l)=丙酮酸-(aq) + HPO2-4(aq)}。反应 {ATP(aq)=cAMP(aq) + 焦磷酸盐(aq)}, {ATP(aq) + 丙酮酸(aq)=ADP(aq) + PEP(aq)} 的表观平衡常数 K' 的文献值，{ATP(aq) + pyruvate(aq) + 磷酸盐(aq)=AMP(aq) + PEP(aq) +焦磷酸盐(aq)}也使用化学平衡模型进行分析。这些计算产生了平衡常数

  DOI：

  10.1016/j.jct.2003.08.002
• 作为产物：
  描述：

  磷烯醇丙酮酸 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 以531 g的产率得到phosphoenolpyruvic acid monopotassium salt
  参考文献：
  名称：

  Synthesis of phosphoenolypyruvate and its use in ATP cofactor regeneration

  摘要：

  DOI：

  10.1021/jo00140a036
• 作为试剂：
  描述：

  D-tagatose 6-phosphate disodium salt 在 盐酸 、 sodium hydroxide 、 phosphoenolpyruvic acid monopotassium salt 、 adenosine 5'-triphosphate disodium salt 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 46.0h， 生成 β-D-Fructopyranose
  参考文献：
  名称：

  d-塔格糖1,6-双磷酸酯的简便酶法从头合成和NMR光谱表征

  摘要：

  摘要从半乳糖醇上生长的大肠杆菌细胞中纯化了需要Zn 2+催化活性的d-塔格糖1,6-二磷酸醛缩酶（Ⅱ类）。醛缩酶是由mol wt〜28000的亚基组成的同型四聚体，其最适pH为7.5，与d-苏式立体化学（99：1）相比，对l-erythro具有高度选择性。这使得它可以与甘油激酶，丙酮酸激酶和磷酸三糖异构酶一起用于偶联酶系统中，从头开始，从二羟基丙酮和磷酸烯醇丙酮酸开始一锅合成d-塔格糖1,6-二磷酸酯（用于原位再生）。量为10 mmol的三磷酸腺苷）。快速的过程与已知的多步化学制备方法相比，在简单性和产率（总产率为40％）方面具有非常好的优势，即使在本工作中对后者进行了改进之后也是如此。在两个磷酸化步骤中都修饰了从d-半乳糖醛酸开始的经典序列：通过应用三价磷酸化试剂二苄基di-N-来酯化1,2：3,4-二-O-异亚丙基-d-塔基呋喃糖。乙基亚磷酰胺随后进行过氧化氢氧化，并且将细菌果糖6-磷

  DOI：

  10.1016/0008-6215(93)87020-s

文献信息

• A Single-Step Asymmetric Phosphodiester Synthesis from Alcohols with Phosphoenolpyruvate Phosphodiester
  作者：Kenzo Yamatsugu、Motomu Kanai、Kohei Fujiyoshi、Shigehiro A. Kawashima

  DOI：10.1055/a-1509-9275

  日期：2021.7

  thus, important to develop a simple and robust way to synthesize them from corresponding alcohols. Here we report a single-step asymmetric phosphodiester synthesis from alcohols with phosphoenolpyruvate phosphodiesters as phosphoryl donors. This transformation allows for the use of various functionalized alcohols as substrates and would be useful for diverse fields including biology and medicine.

  磷酸二酯是在分子科学的不同领域中观察到的重要结构基序。因此，开发一种简单而可靠的方法来从相应的醇合成它们是很重要的。在这里，我们报告了以磷酸烯醇丙酮酸磷酸二酯作为磷酰基供体的醇单步不对称磷酸二酯合成。这种转化允许使用各种功能化醇作为底物，并将用于包括生物学和医学在内的不同领域。
• A Secondary β Deuterium Kinetic Isotope Effect in the Chorismate Synthase Reaction
  作者：Stephen Bornemann、Maria-Elena Theoclitou、Martin Brune、Martin R. Webb、Roger N.F. Thorneley、Chris Abell

  DOI：10.1006/bioo.2000.1174

  日期：2000.8

  observation of kinetic isotope effects using this substrate with both Neurospora crassa and Escherichia coli chorismate synthases. The magnitude of the effects were (D)(V) = 1.08 +/- 0.01 for the N. crassa enzyme and 1.10 +/- 0.02 on phosphate release under single-turnover conditions for the E. coli enzyme. The effects are best rationalised as substantial secondary beta isotope effects. It is most likely

  Chorismate合酶（EC 4.6.1.4）是一种iki草酸酯途径酶，可催化5-磷酸烯醇丙酮酸shi草酸酯3-磷酸酯（EPSP）转化为chorismate。酶反应是不寻常的，因为它涉及C-3磷酸和C-6 proR氢的反式1,4消除，并且对减少黄素的含量有绝对的要求。已经提出了几种机制来解释辅因子需求和反应的立体化学，包括自由基机制。本文介绍了[4-（2）H] EPSP的合成以及使用这种底物与Neurospora crassa和大肠杆菌分支酸合酶的动力学同位素效应的观察。对于N. crassa酶而言，影响的大小为（D）（V）= 1.08 +/- 0.01，对于大肠杆菌酶，在单周转条件下，对磷酸盐释放的影响为（D）（V）= 1.08 +/- 0.01。最好将这些效应合理化为实质性的次级β同位素效应。最有可能的是，C（3）-O键首先在一个未经证实的E1或自由基反应机制中断裂。尽管仅这项研究不
• Isotope Effects on the Enzymatic and Nonenzymatic Reactions of Chorismate
  作者：S. Kirk Wright、Michael S. DeClue、Ajay Mandal、Lac Lee、Olaf Wiest、W. Wallace Cleland、Donald Hilvert

  DOI：10.1021/ja052929v

  日期：2005.9.1

  large 18O isotope effect at the bond-breaking position (1.0482 +/- 0.0005) and a smaller 13C isotope effect at the bond-making position (1.0118 +/- 0.0004) were determined. Isotope effects of similar magnitude characterized the transformations catalyzed by evolutionarily unrelated chorismate mutases from Escherichia coli and Bacillus subtilis. The enzymatic reactions, like their solution counterpart, are

  重要的生物合成中间体分支酸通过两种竞争性途径进行热反应，一种通过消除烯醇丙酮酸侧链产生 4-羟基苯甲酸酯，另一种通过简单的克莱森重排进行预苯甲酸酯化。用同位素标记的分支酸衍生物进行的测量表明，两者都是由烯醇丙酮酸基团的方向控制的协调的 sigmatropic 过程。在 [4-2H] 分支酸的消除反应中，在 60 摄氏度 3 小时后发现大约 60% 的标记存在于丙酮酸中。此外，1.846 +/- 0.057 2H 同位素效应对转移的氢原子和 1.0374 + /- 0.0005 醚氧的 18O 同位素效应表明该过程的过渡态是高度不对称的，氢原子从 C4 到 C9 的转移明显不如 CO 键断裂。在竞争的克莱森重排中，确定了在键断裂位置 (1.0482 +/- 0.0005) 的非常大的 18O 同位素效应和在键合位置 (1.0118 +/- 0.0004) 的较小的 13C 同位素效应。类似量
• [EN] PIN1 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE PIN1 ET UTILISATIONS ASSOCIÉES
  申请人：UNIV CALIFORNIA

  公开号：WO2022032179A1

  公开（公告）日：2022-02-10

  Disclosed herein are, inter alia, compounds modulating activity and methods of use thereof for treating PIN1 -mediated disorders.

  本文公开了调节活性的化合物及其用于治疗PIN1介导的疾病的方法，等等。
• Experimental and Computational Investigation of the Uncatalyzed Rearrangement and Elimination Reactions of Isochorismate
  作者：Michael S. DeClue、Kim K. Baldridge、Peter Kast、Donald Hilvert

  DOI：10.1021/ja056714x

  日期：2006.2.1

  isoprephenate by a facile Claisen rearrangement and the other to salicylate via elimination of the enolpyruvyl side chain. Computation suggests that both processes are concerted but asynchronous pericyclic reactions, with considerable C-O cleavage in the transition state but relatively little C-C bond formation (rearrangement) or hydrogen atom transfer to the enolpyruvyl side chain (elimination). Kinetic

  多功能生物合成中间体异分支酸通过两种竞争性途径在水性缓冲液中分解，一种通过简单的克莱森重排导致异戊二酸酯，另一种通过消除烯醇丙酮酸侧链导致水杨酸化。计算表明，这两个过程是协同但异步的周环反应，在过渡态有相当多的 CO 裂解，但相对较少的 CC 键形成（重排）或氢原子转移到烯醇丙酮酰侧链（消除）。动力学实验表明，重排大约比消除有利 8 倍。此外，通过监测 [2-(2)H] 异分支酸的分解来验证 C2 氢原子向 C9 的转移，其由标记的莽草酸化学酶法制备，通过（2）H NMR光谱和观察[3-（2）H]丙酮酸的出现。最后，用 C2 氘代底物获得的同位素效应与假设周环反应机制的计算非常一致。这些结果为异分支酸变位酶和异分支酸丙酮酸裂解酶的机理研究提供了基准，这两种酶分别催化植物和细菌中的重排和消除反应。