N,O-二甲基-L-酪氨酸 | 52939-33-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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,O-二甲基-L-酪氨酸
• 英文名称: N,O-diMe-L-Tyr
• 英文别名: N,O-Dimethyltyrosine；(2S)-3-(4-methoxyphenyl)-2-(methylamino)propanoic acid
• CAS: 52939-33-0
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: QESMMBKGCOSBNL-JTQLQIEISA-N

物化性质

• 沸点：
  350.9±32.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922509090
• 储存条件：
  存储条件：2-8℃，密封保存，干燥环境。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Mephe(4-meo)-oh
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: H-Mephe(4-meo)-oh
CAS number: 52939-33-0

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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: C11H15NO3.ClH
Molecular weight: 245.7

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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, hydrogen chloride.

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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

反应信息

• 作为反应物：
  描述：

  N,O-二甲基-L-酪氨酸 在 盐酸 、 溴 作用下， 以 水 为溶剂， 反应 22.25h， 以90%的产率得到(+)-(S)-3-(3,5-dibromo-4-methoxyphenyl)-2-methylaminopropanoic acid hydrochloride
  参考文献：
  名称：

  Syntheses of pseudoceramines A–D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges

  摘要：

  在此，我们报告了从海洋海绵中分离出的假精胺 A-D（2â5）和精胺（1）的全合成。合成的化合物证实了所报道的结构，重要的是提供了含有两种不同溴酪氨酸结构单元的非对称精胺类天然产物。与之前报道的序列相比，我们的精胺新合成方法缩短了两个步骤，效率更高。

  DOI：

  10.1039/c1ob06722b
• 作为产物：
  描述：

  (S)-2-(tert-butoxycarbonyl(methyl)amino)-3-(4-methoxyphenyl)propanoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到N,O-二甲基-L-酪氨酸
  参考文献：
  名称：

  Pompanopeptins A and B, new cyclic peptides from the marine cyanobacterium Lyngbya confervoides

  摘要：

  A new 3-amino-6-hydroxy-2-piperidone (Ahp) containing peptolide, pompanopeptin A (1), and a novel N-methyl-2-amino-6-(4'-hydroxyphenyl)hexanoic acid (N-Me-Ahpha) containing cyclic pentapeptide connected with a sixth amino acid residue via a rare ureido linkage, pompanopeptin B (2), were isolated from the marine cyanobacterium Lyngbya confervoides collected from the southeastern coast of Florida. Their planar structures were determined by a combination of NMR spectroscopic analysis and mass spectrometry. The absolute configurations were established using advanced Marfey's method and chiral HPLC analysis of the chemical degradation products. Compound 1 selectively inhibited trypsin over elastase and chymotrypsin, with an IC(50) value of 2.4 mu M; selectivity is conferred by an arginine residue in the cyclic core. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.035

文献信息

• METHOD FOR SYNTHESIZING PEPTIDES IN CELL-FREE TRANSLATION SYSTEM
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20200040372A1

  公开（公告）日：2020-02-06

  An objective of the present invention is to provide methods of synthesizing peptides containing structurally diverse amino acids using cell-free translation systems, which can accomplish excellent translational efficiency as compared to conventional techniques (the conventional techniques being methods which involve preparing aminoacyl-tRNAs which do not have protecting groups outside the translation systems without using ARS, and then adding the prepared aminoacyl-tRNAs into translation systems). In the present invention, it was found that amino acid-containing peptides can be synthesized efficiently by protecting an amino acid linked to tRNA with an appropriate protecting group, and then performing the step of deprotecting the protecting group of the amino acid linked to tRNA and the step of peptide translation from a template nucleic acid in a cell-free translation system in parallel.

  本发明的一个目标是提供使用无细胞翻译系统合成含有结构多样的氨基酸的肽的方法，这些方法可以实现与传统技术相比出色的翻译效率（传统技术是指涉及在翻译系统外部准备没有保护基的氨酰-tRNA而不使用ARS的方法，然后将准备好的氨酰-tRNA添加到翻译系统中）。在本发明中，发现通过用适当的保护基保护与tRNA连接的氨基酸，然后并行进行去保护氨基酸与tRNA连接的保护基的步骤和从模板核酸进行肽翻译的步骤，可以高效地合成含有氨基酸的肽。
• Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate‐Directed Formation of Quinolones versus Quinazolinones
  作者：Manuel Einsiedler、Cooper S. Jamieson、Mark A. Maskeri、Kendall N. Houk、Tobias A. M. Gulder

  DOI：10.1002/anie.202017086

  日期：2021.4.6

  induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine‐2,5‐dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and

  先前的研究表明，Fe II /α-酮戊二酸依赖性双加氧酶AsqJ诱导构巢曲霉在viridicatin生物合成中的骨架重排，从苯并[1,4]二氮杂-2,5-二酮底物生成喹诺酮骨架。我们报告说，仅通过改变苯并二氮杂二酮底物中的取代基，AsqJ即可催化另外的，完全不同的反应。通过底物筛选，功能探针的应用和计算分析来建立这种新机制。AsqJ消费税H 2由合适的苯并[1,4]二氮杂-2-5,5-二酮底物的杂环结构生成CO，生成喹唑啉酮。这种新颖的AsqJ催化途径由复杂底物中的单个取代基控制。AsqJ的这种独特的底物定向反应性可实现喹诺酮或喹唑啉酮的靶向生物催化生成，喹诺酮或喹唑啉酮是两种具有特殊生物医学相关性的生物碱框架。
• Structure of the Dioxygenase AsqJ: Mechanistic Insights into a One-Pot Multistep Quinolone Antibiotic Biosynthesis
  作者：Alois Bräuer、Philipp Beck、Lukas Hintermann、Michael Groll

  DOI：10.1002/anie.201507835

  日期：2016.1.4

  Multienzymatic cascades are responsible for the biosynthesis of natural products and represent a source of inspiration for synthetic chemists. The FeII/α‐ketoglutarate‐dependent dioxygenase AsqJ from Aspergillus nidulans is outstanding because it stereoselectively catalyzes both a ferryl‐induced desaturation reaction and epoxidation on a benzodiazepinedione. Interestingly, the enzymatically formed

  多酶级联反应负责天然产物的生物合成，代表了合成化学家的灵感来源。构巢曲霉Fe II /α-酮戊二酸依赖性双加氧酶AsqJ之所以出色，是因为它立体选择性地催化了在苯并二氮杂二酮上的由Ferryl引起的去饱和反应和环氧化反应。有趣的是，酶促形成的螺环氧化物将非酶重排的6,7-双环骨架弹簧加载到喹诺酮生物碱4'-甲氧基viridicatin的6,6-双环骨架中。在本文中，我们报道了在没有和存在模仿这种特殊的双加氧酶反应周期各个阶段的合成底物，替代物和中间体的情况下，蛋白质的不同晶体结构。
• Dudawalamides A–D, Antiparasitic Cyclic Depsipeptides from the Marine Cyanobacterium <i>Moorea producens</i>
  作者：Jehad Almaliti、Karla L. Malloy、Evgenia Glukhov、Carmenza Spadafora、Marcelino Gutiérrez、William H. Gerwick

  DOI：10.1021/acs.jnatprod.7b00034

  日期：2017.6.23

  A family of 2,2-dimethyl-3-hydroxy-7-octynoic acid (Dhoya)-containing cyclic depsipeptides, named dudawalamides A–D (1–4), was isolated from a Papua New Guinean field collection of the cyanobacterium Moorea producens using bioassay-guided and spectroscopic approaches. The planar structures of dudawalamides A–D were determined by a combination of 1D and 2D NMR experiments and MS analysis, whereas the

  的2,2-二甲基-3-羟基-7-辛炔酸（Dhoya）含环状缩肽，命名为dudawalamides A-d（A家族1 - 4），从蓝藻的巴布亚新几内亚字段集合分离莫雷阿岛producens使用生物测定指导和光谱学方法。杜达拉瓦胺A–D的平面结构是通过1D和2D NMR实验和MS分析的组合确定的，而绝对构型则是通过X射线晶体学，改进的Marfey分析，手性相GCMS和手性相HPLC确定的。Dudawalamides A–D具有广泛的抗寄生虫活性，对哺乳动物细胞的细胞毒性极小。对含Dhoya的脂肽类的比较分析显示，这些NRPS-PKS衍生的代谢物及其衍生物具有令人感兴趣的结构-活性关系特征。
• Majusculamide D and deoxymajusculamide D, two cytotoxins from Lyngbya majuscula
  作者：Richard E. Moore、Michael Entzeroth

  DOI：10.1016/0031-9422(88)80008-6

  日期：1988.1

  Abstract Majusculamide D and deoxymajusculamide D are cytotoxic lipopentapeptides that are minor constituents of a deep-water variety of the marine blue-green alga Lyngbya majuscula from Enewetak.

  摘要 Majusculamide D 和 deoxymajusculamide D 是细胞毒性脂五肽，它们是来自 Enewetak 的海洋蓝绿藻 Lyngbya majuscula 深水品种的次要成分。