D-苯丙氨酰胺盐酸盐 | 71666-94-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他保护氨基酸
• 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-苯丙氨酰胺盐酸盐
• 英文名称: (R)-2-amino-3-phenylpropanamide hydrochloride
• 英文别名: D-Phe-NH2*HCl；D-phenylalaninamide hydrochloride；(R)-phenylalaninamide hydrochloride；H-D-Phe-NH2 hcl；(2R)-2-amino-3-phenylpropanamide;hydrochloride
• CAS: 71666-94-9
• 化学式: C₉H₁₂N₂O*ClH
• 分子量: 200.668
• InChiKey: KLHLGTPNBQXSJT-DDWIOCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  69.1
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 储存条件：
  存储条件：0-5°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-D-Phe-NH2 HCl
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-D-Phe-NH2 HCl
CAS number: 71666-94-9

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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: C9H12N2O.ClH
Molecular weight: 200.7

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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：

  D-苯丙氨酰胺盐酸盐 在 盐酸 作用下， 生成 D-苯丙氨酸
  参考文献：
  名称：

  氨基酸的分辨率。I. 亮氨酸氨肽酶拆分外消旋苯丙氨酸和γ-苯基-α-氨基丁酸

  摘要：

  DL-苯丙酰胺和DL-苯基-氨基丁酸酰胺通过部分纯化的亮氨酸氨肽酶制剂拆分为L-氨基酸和D-氨基酸酰胺。对于 DL-苯丙酰胺，使用离子交换树脂 Amberlite IRA-400 可以方便地分离消化物中的产物，而对于 DL-苯氨基丁酰胺，则使用不同的溶解度。得到的D-氨基酸酰胺盐酸盐部分经酸水解转化为D-氨基酸。

  DOI：

  10.1246/bcsj.31.529
• 作为产物：
  描述：

  alpha-氨基-苯丙酰胺盐酸盐(1:1) 在 5-磷酸吡哆醛 、 氯化亚砜 、 氨 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 D-苯丙氨酰胺盐酸盐
  参考文献：
  名称：

  通过相应的酰胺和腈底物与多酶系统的动态动力学拆分，酶促合成手性苯丙氨酸衍生物

  摘要：

  通过定向进化得到了来自无色杆菌的突变的α-氨基-ε-己内酰胺（ACL）消旋酶（L19V / L78T），其对苯丙氨酰胺的底物特异性得到了提高。在大肠杆菌（pACLmut / pDBFB40）中共表达的来自拟人O鱼SV3的突变型ACL消旋酶和热稳定的突变型D-氨基酸酰胺酶（DaaA）被用于合成（R）-苯丙氨酸和非天然（R）-苯丙氨酸衍生物（4-OH，4-F，3-F和2-F-Phe）的动力学动力学分辨率（DKR）。重组大肠杆菌（E.coli）与DaaA和突变ACL消旋酶基因催化（合成- [R ）-苯丙氨酸与84％产率和99％的ee值由（RS）-苯丙氨酰胺（400 mM）在22小时内。（- [R ）-酪氨酸和4-氟- （[R ）-苯丙氨酸也被有效地从相应的酰胺化合物的合成。我们还共同expresed从编码突变ACL消旋酶和L-氨基酸酰胺酶的两个基因缺陷短波单胞在大肠杆菌和执行的高效生产各种（的小号）

  DOI：

  10.1002/adsc.201100923

文献信息

• Stability against enzymatic hydrolysis of endomorphin-1 analogues containing β-proline
  作者：Giuliana Cardillo、Luca Gentilucci、Alessandra Tolomelli、Maria Calienni、Ahmed R. Qasem、Santi Spampinato

  DOI：10.1039/b301507f

  日期：2003.4.23

  The enantiomer of endomorphin-1 (Tyr-Pro-Trp-PheNH2) and the analogues containing (S)- or (R)-β-proline have been synthesized, and their affinities towards μ-opioid receptors have been measured. As expected, the incubations of the different peptides with some commercially available enzymes showed that the presence of D-residues gave strong resistance towards digestion. The presence of β-proline alone is sufficient to confer good resistance against the hydrolysis of the biologically strategic Pro–Trp bond.

  内啡肽-1（Tyr-Pro-Trp-PheNH2）的对映体及其含（S）-或（R）-β-脯氨酸的类似物已被合成，并测定了它们对μ-阿片受体的亲和力。如预期所料，不同肽与一些商业可用酶的共育显示，D-残基的存在赋予了较强的抵抗消化能力。β-脯氨酸单独的存在就足以赋予生物学上关键的Pro-Trp键良好的抵抗水解能力。
• Synthesis, in vitro ADME profiling and in vivo pharmacological evaluation of novel glycogen phosphorylase inhibitors
  作者：Guang-xin Miao、You-de Wang、Zhi-wei Yan、Li-ying Zhang

  DOI：10.1016/j.bmcl.2020.127117

  日期：2020.7

  A small set of indole-2-carboxamide derivatives identified from a high-throughput screening campaign has been described as a novel, potent, and glucose-sensitive inhibitors of glycogen phosphorylase a (GPa). Among this series of compounds, compound 2 exhibited moderate GP inhibitory activity (IC50 = 0.29 μM), good cellular efficacy (IC50 = 3.24 μM for HepG2 cells and IC50 = 7.15 μM for isolated rat

  从高通量筛选活动中鉴定出的一小批吲哚-2-羧酰胺衍生物已被描述为糖原磷酸化酶a（GPa）的新型，有效且对葡萄糖敏感的抑制剂。其中这一系列化合物中，化合物2显示出中度GP的抑制活性（IC 50  = 0.29μM），良好的细胞效力（IC 50  = 3.24μM为HepG2细胞和IC 50  = 7.15μM为分离的大鼠肝细胞），具有良好的吸收一起分布，代谢和消除（ADME）配置文件。在体内动物研究表明，化合物2显著抑制了肾上腺素诱导的糖尿病小鼠中的增加空腹血糖水平。
• [EN] MU OPIOID RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RÉCEPTEUR OPIOÏDE DE TYPE MU
  申请人：UNIV CALIFORNIA

  公开号：WO2017007695A1

  公开（公告）日：2017-01-12

  Described herein, inter alia, are compositions and methods for modulating mu opioid receptor activity.

  本文描述了用于调节μ阿片受体活性的组合物和方法。
• Methods and compositions for treating amyloid-related diseases
  申请人：Kong Xianqi

  公开号：US20060223855A1

  公开（公告）日：2006-10-05

  Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.

  描述了用于治疗或预防与淀粉样蛋白相关疾病的方法、化合物、药物组合物和试剂盒。
• Synthesis and optimization of novel α-phenylglycinamides as selective TRPM8 antagonists
  作者：Jun-ichi Kobayashi、Hideaki Hirasawa、Tetsuji Ozawa、Tomonaga Ozawa、Hiroo Takeda、Yoshikazu Fujimori、Osamu Nakanishi、Noboru Kamada、Tetsuya Ikeda

  DOI：10.1016/j.bmc.2016.11.049

  日期：2017.1

  overactive bladder and painful bladder syndrome; however, there is a potential risk of low blood pressure. We report herein the synthesis and structure–activity relationships of novel phenylglycine derivatives that led to the identification of KPR-2579 (20l), a TRPM8 selective antagonist. KPR-2579 reduced the number of icilin-induced wet-dog shakes and rhythmic bladder contraction in rats, with no negative

  瞬态受体电位褪黑素8（TRPM8）被无害的感冒和化学物质激活，该通道的拮抗剂被认为对疼痛和泌尿系统疾病有效。有人提出，TRPM8拮抗剂N-（3-氨基丙基）-2-[（（3-甲基苯基）甲基]氧基} -N-（2-噻吩甲基）苯甲酰胺盐酸盐（AMTB）可有效治疗膀胱过度活动症和膀胱疼痛综合症 但是，存在潜在的低血压风险。我们在此报告了新型苯甘氨酸衍生物的合成与结构-活性的关系，从而鉴定了TRPM8选择性拮抗剂KPR-2579（20l）。KPR-2579 减少了依西林诱导的湿狗摇动和节律性膀胱收缩的次数，在有效剂量下对心血管没有负面影响。