D-2-溴苯基丙氨酸 | 267225-27-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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: D-2-溴苯基丙氨酸
• 中文别名: D-2-溴苯丙氨酸；2-溴-D-苯丙氨酸
• 英文名称: 2-bromo-D-phenylalanine
• 英文别名: (R)-2-bromophenylalanine；(2R)-2-amino-3-(2-bromophenyl)propanoic acid
• CAS: 267225-27-4
• 化学式: C₉H₁₀BrNO₂
• 分子量: 244.088
• InChiKey: JFVLNTLXEZDFHW-MRVPVSSYSA-N

物化性质

• 沸点：
  363.2±32.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 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：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

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：
  H315,H319,H335
• 储存条件：
  存储温度应保持在-15°C。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: D-2-Bromophenylalanine
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-Bromophenylalanine
CAS number: 267225-27-4

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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, refrigerated.
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: C9H10BrNO2
Molecular weight: 244.1

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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 bromide.

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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-溴苯基丙氨酸 在 sodium tetrahydroborate 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (2R)-2-amino-3-(2-bromophenyl)propan-1-ol
  参考文献：
  名称：

  基于非对映选择性Pictet-Spengler的手性四氢异喹啉D1增效剂的合成。

  摘要：

  D1增效剂手性四氢异喹啉的实用合成已通过非对映选择性Pictet-Spengler方法获得所需的反式立体化学。通过结晶进行动态动力学拆分，可得到高产率的N-（苯基磺酰基）烷基恶唑烷酮，当暴露于多种路易斯酸时会转化为酰基亚胺离子，从而导致非对映选择性的Pictet-Spengler环化反应。以可商购获得的R -2-溴苯丙氨酸开始的八步线性合成反应以54％的总收率得到手性四氢异喹啉1。

  DOI：

  10.1021/acs.joc.0c00177
• 作为产物：
  描述：

  DL-2-溴苯丙氨酸 在 phenylalanine ammonia-lyase from Petroselinum crispum 作用下， 以 aq. buffer 为溶剂， 反应 168.0h， 以99%的产率得到
  参考文献：
  名称：

  一种来自南极假酶的新型苯丙氨酸氨裂合酶，用于非天然氨基酸的立体选择性生物转化

  摘要：

  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

  DOI：

  10.1016/j.cattod.2020.04.002

文献信息

• [EN] AZASULFURYLPEPTIDE-BASED CD36 MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS CD36 À BASE D'AZASULFURYLPEPTIDES ET UTILISATIONS DE CEUX-CI
  申请人：RSEM LTD PARTNERSHIP

  公开号：WO2016029324A1

  公开（公告）日：2016-03-03

  Novel azasulfuryl-containing peptidomimetics capable of inhibiting CD36 activity are disclosed. Use of these azasulfuryl-containing peptidomimetics for the treatment of CD36-related diseases, disorders or conditions, including TLR2-mediated inflammatory disease, disorder or condition, and methods of obtaining such azasulfuryl-containing peptidomimetics, are also disclosed.

  揭示了能够抑制CD36活性的新型含氮硫酰基的肽类模拟物。还揭示了利用这些含氮硫酰基的肽类模拟物治疗与CD36相关的疾病、紊乱或状况，包括TLR2介导的炎症性疾病、紊乱或状况的用途，以及获取这种含氮硫酰基的肽类模拟物的方法。
• Angiotensin-1-Receptor Antagonists
  申请人：Ferring B.V.

  公开号：US20170349629A1

  公开（公告）日：2017-12-07

  In one aspect, this disclosure features compounds of formula (I) or a pharmaceutically acceptable salt thereof: AA1-Arg-Val-AA4-AA5-His-Pro-AA8-OH   (I), in which AA1, AA4, AA5, and AA8 are defined in the specification. The compounds of formula (I) can be used to treat hypertension (e.g., hypertension induced by pregnancy), preeclampsia, or a renal disease induced by pregnancy.

  在一个方面，这个披露涉及到式(I)的化合物或其药用盐： AA1-Arg-Val-AA4-AA5-His-Pro-AA8-OH (I)， 其中AA1，AA4，AA5和AA8在规范中有定义。式(I)的化合物可用于治疗高血压（例如，妊娠引起的高血压），子痫前期，或妊娠引起的肾脏疾病。
• 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
• [EN] CHEMOKINE CXCR4 RECEPTOR MODULATORS AND USES RELATED THERETO<br/>[FR] MODULATEURS DU RÉCEPTEUR CXCR4 DE CHIMIOKINE ET LEURS UTILISATIONS
  申请人：UNIV EMORY

  公开号：WO2018156595A1

  公开（公告）日：2018-08-30

  The disclosure relates to chemokine CXCR4 receptor modulators and uses related thereto. The receptor modulators can be formulated to form pharmaceutical compositions comprising the disclosed compounds or pharmaceutically acceptable salts or prodrugs thereof. The compositions may be used for managing CXCR4 related conditions, typically prevention or treatment of viral infections abnormal cellular proliferation, retinal degeneration, inflammatory diseases, or as an immunostimulant or immunosuppressant or for managing cancer and may be administered with another active ingredient such as an antiviral agent or chemotherapeutic agent.

  该披露涉及趋化因子CXCR4受体调节剂及其相关用途。这些受体调节剂可以配制成包含所披露的化合物或其药学上可接受的盐或前药的药物组合物。这些组合物可用于管理与CXCR4相关的疾病，通常用于预防或治疗病毒感染、异常细胞增殖、视网膜退化、炎症性疾病，或作为免疫刺激剂或免疫抑制剂，或用于癌症管理，并可与另一种活性成分一起给药，如抗病毒药物或化疗药物。