D-丙氨酰-苯丙氨酸 | 3061-95-8

• 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-丙氨酰-苯丙氨酸
• 英文名称: D-Ala-Phe-OH
• 英文别名: D-Ala-L-Phe；D-Ala-Phe；H-D-Ala-phe-OH；(2S)-2-[[(2R)-2-aminopropanoyl]amino]-3-phenylpropanoic acid
• CAS: 3061-95-8
• 化学式: C₁₂H₁₆N₂O₃
• mdl: MFCD00066030
• 分子量: 236.271
• InChiKey: OMNVYXHOSHNURL-SCZZXKLOSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-D-Ala-phe-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-D-Ala-phe-oh
CAS number: 3061-95-8

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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: C12H16N2O3
Molecular weight: 236.3

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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-丙氨酰-苯丙氨酸 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 H-Tyr-D-Ala-Phe-Gly-Val-Val-Asp-NH2
  参考文献：
  名称：

  Unique sequence in deltorphin C confers structural requirement for δ opioid receptor selectivity

  摘要：

  A series of deltorphin C (H-Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2) analogues were synthesized to assess the consequences of changing anionic and hydrophobic residues on delta receptor selectivity. Analogues with altered C-terminal groups, inverted sequences, or esterified with tert-butyl, benzyl, or ethyl groups revealed that high delta selectivity required an unmodified amino acid sequence. Shifts of Asp and hydrophobic residues decreased delta selectivity due to loss in delta affinity (5- to almost-equal-to 700-fold); mu affinity was unchanged or increased 14-fold. Suppression of charge or deamidation diminished delta selectivity through reduced delta and modified mu affinities. Data provide evidence that a negative charge does not a priori guarantee high selectivity and specific alignment of anionic and hydrophobic residues might facilitate optimum spatial configuration which complements the 8 receptor binding site.

  DOI：

  10.1016/0223-5234(92)90113-f
• 作为产物：
  描述：

  L-苯基丙氨酸叔丁酯 在 sodium hydroxide 、 N-羟基丁二酰亚胺 、 bis-(trifluoroacetoxy)-iodo-benzene 、 氨 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 D-丙氨酰-苯丙氨酸
  参考文献：
  名称：

  逆向二肽的1 H NMR构型相关性：用于确定“脑啡肽酶”抑制剂的绝对构型。立体化学与酶识别之间的关系。

  摘要：

  噻吩[N- [2（RS）-（巯基甲基）-1-氧代-3-苯基丙基]甘氨酸]和噻吩基反[3-[[1（RS）-（巯基甲基）-2-苯基乙基]的立体定向合成。据报道，有两种高效的脑啡肽酶抑制剂，即一种参与脑啡肽代谢的中性内肽酶，即氨基] -3-氧代丙酸]。由于快速的异构化过程，不能通过经典方法分离包含2-取代的丙二酰基部分的反式-硫烷的衍生物。然而，通过HPLC实现了这些逆硫代硫烷衍生物的非对映异构体混合物的分离。通过使用NMR构型相关性确定每种异构体的绝对构型。各种抑制剂的抑制能力表明，在硫醇系列中，对脑啡肽酶的亲和力与2-（巯基甲基）-1-氧代-3-苯基丙基部分的立体化学无关。相反，在逆硫氰酸系列中，观察到两种对映体的抑制活性相差100倍。这表明在酶的活性位点上，这两种抑制剂的构象行为存在很大差异。

  DOI：

  10.1021/jm00155a027

文献信息

• Investigations of the In-vitro Metabolism of Three Opioid Tetrapeptides by Pancreatic and Intestinal Enzymes
  作者：Eva Krondahl、Hans Von Euler-Chelpin、Achim Orzechowski、Gunilla Ekström、Hans Lennernäs

  DOI：10.1211/0022357001774642

  日期：2010.2.18

  , Tyr-D-Arg-Phe-Phe-NH2 and Tyr-D-Ala-Phe-Phe-NH2, was investigated in the presence of pure pancreatic enzymes (trypsin, chymotrypsin, elastase, carboxypeptidase A and carboxypeptidase B), as well as in the presence of pure carboxylesterase and aminopeptidase N. The cleavage patterns of the pure pancreatic enzymes were then compared with those found in rat and human jejunal fluid. Metabolism was also

  在纯存在下研究了三种阿片类四肽Tyr-D-Arg-Phe-Nva-NH2，Tyr-D-Arg-Phe-Phe-NH2和Tyr-D-Ala-Phe-Phe-NH2的代谢胰酶（胰蛋白酶，胰凝乳蛋白酶，弹性蛋白酶，羧肽酶A和羧肽酶B），以及在纯羧酸酯酶和氨肽酶N的存在下。然后将纯胰酶的裂解模式与大鼠和人空肠液中的裂解模式进行比较。还研究了来自不同肠道区域（十二指肠，空肠，回肠和结肠）的匀浆以及大鼠肠细胞胞浆中的代谢。在空肠匀浆中研究了各种蛋白酶抑制剂的作用。通过高效液相色谱法测定亲本肽，并通过液相色谱-质谱法鉴定代谢产物。在纯酶中，胰酶胰凝乳蛋白酶，胰蛋白酶和羧肽酶A观察到肽水解最快。在大多数情况下，它们形成了相应的脱酰胺四肽（胰凝乳蛋白酶和胰蛋白酶）或三肽，缺少C末端氨基酸（羧肽酶）。一种）。发现所有三种肽的肠道代谢率均存在区域差异（P <0.001），在空肠和/或结肠匀浆中观察到的率最高。脱
• Unique sequence in deltorphin C confers structural requirement for δ opioid receptor selectivity
  作者：LH Lazarus、S Salvadori、P Grieco、WE Wilson、R Tomatis

  DOI：10.1016/0223-5234(92)90113-f

  日期：1992.11

  A series of deltorphin C (H-Tyr-D-Ala-Phe-Asp-Val-Val-Gly-NH2) analogues were synthesized to assess the consequences of changing anionic and hydrophobic residues on delta receptor selectivity. Analogues with altered C-terminal groups, inverted sequences, or esterified with tert-butyl, benzyl, or ethyl groups revealed that high delta selectivity required an unmodified amino acid sequence. Shifts of Asp and hydrophobic residues decreased delta selectivity due to loss in delta affinity (5- to almost-equal-to 700-fold); mu affinity was unchanged or increased 14-fold. Suppression of charge or deamidation diminished delta selectivity through reduced delta and modified mu affinities. Data provide evidence that a negative charge does not a priori guarantee high selectivity and specific alignment of anionic and hydrophobic residues might facilitate optimum spatial configuration which complements the 8 receptor binding site.
• Proton NMR configurational correlation for retro-inverso dipeptides: application to the determination of the absolute configuration of "enkephalinase" inhibitors. Relationships between stereochemistry and enzyme recognition
  作者：M. C. Fournie-Zaluski、E. Lucas-Soroca、J. Devin、B. P. Roques

  DOI：10.1021/jm00155a027

  日期：1986.5

  A stereospecific synthesis of thiorphan [N-[2(RS)-(mercaptomethyl)-1-oxo-3-phenylpropyl]glycine] and retro-thiorphan [3-[[1(RS)-(mercaptomethyl)-2-phenylethyl]amino]-3-oxopropanoic acid], two highly potent inhibitors of enkephalinase, a neutral endopeptidase involved in enkephalin metabolism, is reported. Due to a rapid isomerization process, derivatives of retro-thiorphan, which contains a 2-substituted

  噻吩[N- [2（RS）-（巯基甲基）-1-氧代-3-苯基丙基]甘氨酸]和噻吩基反[3-[[1（RS）-（巯基甲基）-2-苯基乙基]的立体定向合成。据报道，有两种高效的脑啡肽酶抑制剂，即一种参与脑啡肽代谢的中性内肽酶，即氨基] -3-氧代丙酸]。由于快速的异构化过程，不能通过经典方法分离包含2-取代的丙二酰基部分的反式-硫烷的衍生物。然而，通过HPLC实现了这些逆硫代硫烷衍生物的非对映异构体混合物的分离。通过使用NMR构型相关性确定每种异构体的绝对构型。各种抑制剂的抑制能力表明，在硫醇系列中，对脑啡肽酶的亲和力与2-（巯基甲基）-1-氧代-3-苯基丙基部分的立体化学无关。相反，在逆硫氰酸系列中，观察到两种对映体的抑制活性相差100倍。这表明在酶的活性位点上，这两种抑制剂的构象行为存在很大差异。