D-2-硝基苯丙氨酸 | 169383-17-9

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 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: D-2-硝基苯丙氨酸
• 中文别名: 2-硝基-D-苯丙氨酸
• 英文名称: o-nitro-D-phenylalanine
• 英文别名: (R)-2-amino-3-(2-nitrophenyl)propanoic acid；(2R)-2-amino-3-(2-nitrophenyl)propanoic acid
• CAS: 169383-17-9
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: SDZGVFSSLGTJAJ-SSDOTTSWSA-N

物化性质

• 沸点：
  385.4±32.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: D-2-Nitrophenylalanine
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: D-2-Nitrophenylalanine
CAS number: 169383-17-9

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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: C9H10N2O4
Molecular weight: 210.2

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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.

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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：

  D-2-硝基苯丙氨酸 在 D-amino acid oxidase 、 水 、 氧气 作用下， 生成 邻硝基苯基丙酮酸
  参考文献：
  名称：

  苯丙氨酸氨裂解酶合成 D-和 L-苯丙氨酸衍生物：多酶级联过程

  摘要：

  通过将苯丙氨酸解氨酶 (PAL) 胺化与化学酶脱外消旋（基于立体选择性氧化和非选择性还原）。还开发了一种简单的高通量固相筛选方法来鉴定具有较高非天然D-苯丙氨酸形成率的 PAL。在化学酶级联中利用了最佳变体，从而提高了D配置产品的产量和 ee 值。此外，该系统还扩展到制备低浓度的L-苯丙氨酸。ee 值使用PAL胺化。

  DOI：

  10.1002/anie.201410670
• 作为产物：
  描述：

  2-nitrocinnamic acid 在 ammonium hydroxide 、 phenylalanine ammonia-lyase from Anabaena variabilis N₃₄₇A mutant 、 ammonia borane 、 L-amino acid deaminase from Proteus mirabilis 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 D-2-硝基苯丙氨酸
  参考文献：
  名称：

  使用苯丙氨酸氨分解酶和L-氨基酸脱氨酶一锅法合成D-芳基丙氨酸。

  摘要：

  来自鱼腥藻的苯丙氨酸氨裂合酶（AvPAL）催化取代基反式肉桂酸（t-CA）的胺化反应，由于其立体选择性低，可生成外消旋的D，L-对映体芳基丙氨酸混合物。为了生产高光学纯度的D-芳基丙氨酸，期望具有高D选择性的改性AvPAL。在分析催化机理和结构的基础上，提出了活性位点的Asn347残基来控制立体选择性。因此，将Asn347突变以构建突变体AvPAL-N347A，AvPAL-N347A对D-对映体芳丙氨酸的立体选择性比野生型AvPAL（WtPAL）高2.3倍。此外，反应溶液中残留的L-对映体产物可以通过PmLAAD的立体选择性氧化和还原剂NH3BH3的非选择性还原转化为D-对映体产物。在最佳条件下，D-苯丙氨酸的t-CA转化率和光学纯度（对映体过量（eeD））分别达到82％和超过99％。这两种酶对多种底物均显示出活性，可用于有效合成苯环上具有不同基团的D-芳基丙氨酸。在这些D-芳基丙氨酸中，

  DOI：

  10.1007/s12010-018-2794-3

文献信息

• A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids
  作者：Andrea Varga、Pál Csuka、Orlavanah Sonesouphap、Gergely Bánóczi、Monica Ioana Toşa、Gabriel Katona、Zsófia Molnár、László Csaba Bencze、László Poppe、Csaba Paizs

  DOI：10.1016/j.cattod.2020.04.002

  日期：2021.4

  derivatives (rac-1a-s) by enzymatic ammonia elimination and also in the enantiotope selective ammonia addition reactions to cinnamic acid derivatives (2a-s). The enantiotope selectivity of PzaPAL with o-, m-, p-fluoro-, o-, p-chloro- and o-, m-bromo-substituted cinnamic acids proved to be higher than that of PcPAL.

  通过针对已知的PAL序列筛选微生物基因组，鉴定了一种新型的嗜冷酵母南极假单胞菌（Pza PAL）苯丙氨酸解氨酶。与真核生物的已知PAL相比，Pza PAL具有显着不同的底物结合口袋，带有一个延伸的环（长26 aa）连接到活性位点的芳香环结合区域。表征了在大肠杆菌中表达的重组Pza PAL的一般性质，包括该新PAL与1-苯丙氨酸（S）-1a和其他外消旋取代苯丙氨酸rac - 1b-g，k的动力学特征。。在大多数情况下，Pza PAL的营业额明显高于Petroselinum crispum（Pc PAL）的PAL。最后，在外消旋苯丙氨酸衍生物（rac - 1a-s）通过酶促氨消除的动力学拆分以及对映体选择性氨加成肉桂酸衍生物（2a-s）的动力学拆分中，比较了Pza PAL和Pc PAL的生物催化性能。。的enantiotope选择性PZA PAL与ö - ，米- ，p -氟，ø - ，p氯代和ø
• Phenylalanine Ammonia Lyase Catalyzed Synthesis of Amino Acids by an MIO-Cofactor Independent Pathway
  作者：Sarah L. Lovelock、Richard C. Lloyd、Nicholas J. Turner

  DOI：10.1002/anie.201311061

  日期：2014.4.25

  MIO‐independent reaction pathway, which proceeds in a non‐stereoselective manner and results in the generation of both L‐ and D‐phenylalanine derivatives, is described. The mechanism of the MIO‐independent pathway is explored through isotopic‐labeling studies and mutagenesis of key active‐site residues. The results obtained are consistent with amino acid deamination occurring by a stepwise E1cB elimination mechanism

  苯丙氨酸解氨酶 (PAL) 属于 4-亚甲基咪唑-5-酮 (MIO) 辅因子依赖性酶家族，其负责在真核生物和原核生物中将L-苯丙氨酸转化为反式肉桂酸。在高氨浓度条件下，这种脱氨反应是可逆的，因此人们对开发 PAL 作为非天然氨基酸的对映选择性合成的生物催化剂有相当大的兴趣。在此发现了一种以前未观察到的竞争性 MIO 非依赖性反应途径，该反应途径以非立体选择性方式进行并导致L-和D的产生描述了-苯丙氨酸衍生物。通过同位素标记研究和关键活性位点残基的诱变探索了 MIO 非依赖性途径的机制。获得的结果与通过逐步 E 1 cB 消除机制发生的氨基酸脱氨基作用一致。
• Enantioselective organocatalytic α-sulfamidation of aldehydes using sulfonyl azides
  作者：Raymond J. McGorry、Stacey K. Allen、Micha D. Pitzen、Thomas C. Coombs

  DOI：10.1016/j.tetlet.2017.10.063

  日期：2017.12

  Enantioselective organocatalytic α-sulfamidation of unbranched aldehydes is described using MacMillan’s second-generation imidazolidinone catalyst and o-nitrobenzenesulfonyl azide. The reactions are highly stereoselective (89.9–96.3% ee) with yields up to 71%. A strong correlation between aldehyde structure and product yield was found to exist, with 3-arylpropanals providing the best results. Application

  描述了使用麦克米兰的第二代咪唑烷酮催化剂和邻硝基苯磺酰基叠氮化物对非支链醛的对映选择性有机催化α-磺酰胺化反应。反应是高度立体选择性的（89.9–96.3％ee），产率高达71％。发现醛结构与产物产率之间存在强相关性，其中3-芳基丙醛提供最佳结果。介绍了在功能化氨基酸合成中的应用。
• Lipid probes and uses thereof
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US10168342B2

  公开（公告）日：2019-01-01

  Disclosed herein are methods, compositions, probes, assays and kits for identifying a lipid binding protein as a drug binding target. Also disclosed herein are methods, compositions, and probes for mapping a ligand binding site on a lipid binding protein, identification of lipid binding proteins, generating drug-lipid binding protein profiles, high throughput drug screening, and identification of drugs as potential lipid binding protein ligands.

  披露了用于识别脂质结合蛋白作为药物结合靶点的方法、组合物、探针、检测和试剂盒。此外，还披露了用于绘制脂质结合蛋白上的配体结合位点、识别脂质结合蛋白、生成药物-脂质结合蛋白轮廓、高通量药物筛选以及识别作为潜在脂质结合蛋白配体的药物的方法、组合物和探针。
• The Bacterial Ammonia Lyase EncP: A Tunable Biocatalyst for the Synthesis of Unnatural Amino Acids
  作者：Nicholas J. Weise、Fabio Parmeggiani、Syed T. Ahmed、Nicholas J. Turner

  DOI：10.1021/jacs.5b07326

  日期：2015.10.14

  deracemization cascades (giving (S)- or (R)-α-phenylalanine derivatives, respectively), and also eukaryotic phenylalanine aminomutases (PAMs) for the synthesis of the (R)-β-products. Herein, we present the investigation of another family member, EncP from Streptomyces maritimus, thereby expanding the biocatalytic toolbox and enabling the production of the missing (S)-β-isomer. EncP was found to convert

  I类裂解酶家族的酶催化氨向丙烯酸芳基酯的不对称加成，产生作为产物的高价值氨基酸。最近的例子包括使用苯丙氨酸氨裂解酶 (PAL)，单独使用或作为去消旋级联的途径（分别提供 (S)- 或 (R)-α-苯丙氨酸衍生物），以及真核苯丙氨酸氨基变位酶 (PAM) (R)-β-产物的合成。在此，我们介绍了对来自 Streptomyces maritimus 的另一个家族成员 EncP 的研究，从而扩展了生物催化工具箱并能够生产缺失的 (S)-β-异构体。发现 EncP 将一系列芳基丙烯酸酯转化为 (S)-α- 和 (S)-β-芳基丙氨酸的混合物，其区域选择性与每个底物环上的吸电子/供电子基团的强度相关。野生型酶的低区域选择性通过基于结构的合理设计得到解决，以产生三种对α-或β-产物具有改变偏好的变体。通过检查各种生物催化剂/底物组合，证明可以调整反应的胺化模式，以根据需要实现 99:1 和 1:99 之间的