苄基L-alpha-谷氨酰t胺化物盐酸盐(1:1) | 63091-89-4

• 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: 苄基L-alpha-谷氨酰t胺化物盐酸盐(1:1)
• 英文名称: Glu(OBn)-NH2 hydrochloride
• 英文别名: H-Glu(obzl)-NH2 hcl；benzyl (4S)-4,5-diamino-5-oxopentanoate;hydrochloride
• CAS: 63091-89-4
• 化学式: C₁₂H₁₆N₂O₃*ClH
• 分子量: 272.732
• InChiKey: HSXVFJRDTASLQJ-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.4
• 氢给体数：
  3
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Glu(OBzl)-NH2 HCl
Synonyms: L-Glutamic acid gamma-benzyl ester alfa-amide hydrochloride

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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-Glu(OBzl)-NH2 HCl
CAS number: 63091-89-4

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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.
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.ClH
Molecular weight: 272.7

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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：

  苄基L-alpha-谷氨酰t胺化物盐酸盐(1:1) 在 weakly basic Amberlyst-A₂₁ 、 mercury dichloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 3-{(S)-5-Oxo-2-[(E)-3,4,5-trimethoxy-phenylimino]-imidazolidin-4-yl}-propionic acid benzyl ester
  参考文献：
  名称：

  肽杂环共轭物：用于合成N末端2-亚氨基乙内酰脲的edman降解方案。

  摘要：

  [反应：见正文]改进的Edman降解程序提供了一种在α-氨基酸酰胺或肽的N末端引入杂环的有效方法。肽与异硫氰酸酯反应，然后通过弱亲核性相邻酰胺氮的分子内环化，对中间硫脲进行脱氢巯基化捕集，生成亚氨基乙内酰脲。亚氨基乙内酰脲的溶液相平行合成以及由二肽和三肽衍生的亚氨基乙内酰脲的聚合物支持的合成也得以实现。

  DOI：

  10.1021/ol034032d
• 作为产物：
  描述：

  benzyl N-tert-butyloxycarbonyl-L-γ-glutamate α-amide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 生成 苄基L-alpha-谷氨酰t胺化物盐酸盐(1:1)
  参考文献：
  名称：

  Phosphotyrosine-Containing Dipeptides as High-Affinity Ligands for the p56^lck SH2 Domain

  摘要：

  Src homology-2 (SH2) domains are noncatalytic motifs containing approximately 100 amino acid residues that are involved in intracellular signal transduction. The phosphotyrosine-containing tetrapeptide Ac-pYEEI binds to the SH2 domain of p.56(lck) (Lck) with an affinity of 0.1 mu M. Starting from Ac-pYEEI, we have designed potent antagonists of the Lck SH2 domain which are reduced in peptidic character and in which the three carboxyl groups have been eliminated. The two C-terminal amino acids (EI) have been replaced by benzylamine derivatives and the pY + 1 glutamic acid has been substituted with leucine. The best C-terminal fragment identified, (S)-1-(4-isopropylphenyl)ethylamine, binds to the Lck SH2 domain better than the C-terminal dipeptide EI. Molecular modeling suggests that the substituents at the 4-position of the phenyl ring occupy the pY + 3 lipophilic pocket in the SH2 domain originally occupied by the isoleucine side chain. This new series of phosphotyrosine-containing dipeptides binds to the Lck SH2 domain with potencies comparable to that of tetrapeptide 1.

  DOI：

  10.1021/jm980612i

文献信息

• [EN] HETEROCYCLIC DERIVATIVES FOR TREATMENT OF HYPERLIPIDEMIA AND RELATED DISEASES<br/>[FR] DERIVES HETEROCYCLIQUES POUR LE TRAITEMENT DE L'HYPERLIPIDEMIE ET DE MALADIES ASSOCIEES
  申请人：AVANIR PHARMACEUTICALS

  公开号：WO2005123686A1

  公开（公告）日：2005-12-29

  The present invention provides compositions adapted to enhance reverse cholesterol transport in mammals. The compositions are suitable for oral delivery and useful in the treatment and/or prevention of hypercholesterolemia, atherosclerosis and associated cardiovascular diseases.

  本发明提供了适用于增强哺乳动物体内逆向胆固醇转运的组合物。这些组合物适合口服给药，并可用于治疗和/或预防高胆固醇血症、动脉粥样硬化及相关心血管疾病。
• Chemical Synthesis of<i>N</i>-Acetylmuramyl Peptides with Partial Structures of Bacterial Cell Wall and Their Analogs in Relation to Immunoadjuvant Activities
  作者：Shoichi Kusumoto、Yuzo Tarumi、Kazuhiro Ikenaka、Tetsuo Shiba

  DOI：10.1246/bcsj.49.533

  日期：1976.2

  in Staphylococcus aureus were synthesized in order to elucidate the minimum effective structure responsible for immunoadjuvant activity of bacterial cell walls. In view of the finding that N-acetylmuramyl-L-alanyl-D-isoglutamine was the least structure moiety for exhibition of the activity, nine analogs of either N-acetylmuramyl amino acid or N-acetylmuramyl dipeptide were also synthesized.

  为了阐明负责细菌细胞壁免疫佐剂活性的最小有效结构，合成了对应于金黄色葡萄球菌细胞壁部分结构的连续长度的 N-乙酰胞壁酰肽。鉴于发现 N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺是表现活性最少的结构部分，还合成了 N-乙酰胞壁酰氨基酸或 N-乙酰胞壁酰二肽的九种类似物。
• Immunologically active dipeptidyl saccharides and methods of preparation
  申请人：Merck & Co., Inc.

  公开号：EP0014159B1

  公开（公告）日：1982-07-14
• Peptide Heterocycle Conjugates:  A Diverted Edman Degradation Protocol for the Synthesis of N-Terminal 2-Iminohydantoins
  作者：Ghotas Evindar、Robert A. Batey

  DOI：10.1021/ol034032d

  日期：2003.4.1

  [reaction: see text] A modified Edman degradation procedure provides an effective means of introducing a heterocycle at the N-terminus of an alpha-amino acid amide or peptide. Reaction of a peptide with an isothiocyanate, followed by dehydrothiolative trapping of the intermediate thiourea, by intramolecular cyclization of the weakly nucleophilic adjacent amide nitrogen, generates an iminohydantoin

  [反应：见正文]改进的Edman降解程序提供了一种在α-氨基酸酰胺或肽的N末端引入杂环的有效方法。肽与异硫氰酸酯反应，然后通过弱亲核性相邻酰胺氮的分子内环化，对中间硫脲进行脱氢巯基化捕集，生成亚氨基乙内酰脲。亚氨基乙内酰脲的溶液相平行合成以及由二肽和三肽衍生的亚氨基乙内酰脲的聚合物支持的合成也得以实现。
• Phosphotyrosine-Containing Dipeptides as High-Affinity Ligands for the p56<i>^lck</i> SH2 Domain
  作者：Montse Llinàs-Brunet、Pierre L. Beaulieu、Dale R. Cameron、Jean-Marie Ferland、Jean Gauthier、Elise Ghiro、James Gillard、Vida Gorys、Martin Poirier、Jean Rancourt、Dominik Wernic、Raj Betageri、Mario Cardozo、Scott Jakes、Suzanne Lukas、Usha Patel、John Proudfoot、Neil Moss

  DOI：10.1021/jm980612i

  日期：1999.2.1

  Src homology-2 (SH2) domains are noncatalytic motifs containing approximately 100 amino acid residues that are involved in intracellular signal transduction. The phosphotyrosine-containing tetrapeptide Ac-pYEEI binds to the SH2 domain of p.56(lck) (Lck) with an affinity of 0.1 mu M. Starting from Ac-pYEEI, we have designed potent antagonists of the Lck SH2 domain which are reduced in peptidic character and in which the three carboxyl groups have been eliminated. The two C-terminal amino acids (EI) have been replaced by benzylamine derivatives and the pY + 1 glutamic acid has been substituted with leucine. The best C-terminal fragment identified, (S)-1-(4-isopropylphenyl)ethylamine, binds to the Lck SH2 domain better than the C-terminal dipeptide EI. Molecular modeling suggests that the substituents at the 4-position of the phenyl ring occupy the pY + 3 lipophilic pocket in the SH2 domain originally occupied by the isoleucine side chain. This new series of phosphotyrosine-containing dipeptides binds to the Lck SH2 domain with potencies comparable to that of tetrapeptide 1.