L-异谷氨酰胺 | 636-65-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酰胺类衍生物
• 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: L-异谷氨酰胺
• 英文名称: glutamine
• 英文别名: Isoglutamin；(4S)-5-amino-4-azaniumyl-5-oxopentanoate
• CAS: 636-65-7
• 化学式: C₅H₁₀N₂O₃
• 分子量: 146.146
• InChiKey: AEFLONBTGZFSGQ-VKHMYHEASA-N

物化性质

• 熔点：
  160 °C
• 比旋光度：
  D21 +20.5° (c = 6.1 in H2O)
• 沸点：
  423.1±40.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)
• 溶解度：
  轻微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-Glu-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-Glu-nh2 hcl
CAS number: 636-65-7

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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: C5H10N2O3.ClH
Molecular weight: 182.6

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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：

  L-异谷氨酰胺 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 生成 arginyl-glutamine
  参考文献：
  名称：

  THE PREPARATION OFL-ARGINYL DIPEPTIDES OF ASPARAGINE, GLUTAMINE, AND SOME BASIC AMINO ACIDS

  摘要：

  以下二肽的合成过程如下：L-精氨酰-L天冬酰胺酸醋酸盐、L-精氨酰-L谷氨酰胺醋酸盐、L-精氨酰-L赖氨酸二醋酸盐和L-精氨酰-L鸟氨酸二醋酸盐。前两者通过将α-羧苄氧基-ω-硝基-L-精氨酸的混合酸酐直接与L-天冬酰胺或L-谷氨酸偶联制备而成；对产生的中间体进行催化氢解反应得到二肽。另外两者通过将α-羧苄氧基-L-精氨酸与ω-羧苄氧基-L-赖氨酸甲酯盐或ω-羧苄氧基-L-鸟氨酸甲酯盐与N,N'-二环己基-碳二亚胺一起反应得到；需要皂化和氢化才能揭示所得的二肽。

  DOI：

  10.1139/v60-262
• 作为产物：
  描述：

  N-benzyloxycarbonyl-L-glutamic acid-1-hydrazide 在 甲醇 、 乙醇 、 镍 、 钯 作用下， 生成 L-异谷氨酰胺
  参考文献：
  名称：

  Narita, Nippon Kagaku Zasshi, 1953, vol. 74, p. 832

  摘要：

  DOI：

文献信息

• Peptide ligation by chemoselective aminonitrile coupling in water
  作者：Pierre Canavelli、Saidul Islam、Matthew W. Powner

  DOI：10.1038/s41586-019-1371-4

  日期：2019.7

  N-to-C peptide ligation. Our model unites prebiotic aminonitrile synthesis and biological α-peptides, suggesting that short N-acyl peptide nitriles were plausible substrates during early evolution.Prebiotic peptide formation is achieved through chemoselective, high-yielding ligation of α-aminonitriles in water, showing selectivity for α-peptide coupling and tolerance of all proteinogenic amino acid residues

  酰胺键的形成是化学和生物学中最重要的反应之一 1-4，但目前还没有化学方法可以在水中实现 α-肽连接，从而耐受肽连接位点的所有 20 种蛋白质氨基酸。通用遗传密码确立了肽的生物学作用早于生命最后一个普遍的共同祖先，并且肽在生命起源中发挥了重要作用5-9。硫在柠檬酸循环、非核糖体肽合成和聚酮化合物生物合成中的重要作用指向在生命进化过程中，硫酯依赖性肽连接先于 RNA 依赖性蛋白质合成 5,9-13。然而，尚未证明氨酰基硫酯形成的稳健机制。在这里，我们报告了一种化学选择性，高产 α-氨基腈连接，仅利用益生元合理的分子——硫化氢、硫代乙酸盐 12,14 和铁氰化物 12,14-17 或氰基乙炔 8,14——在水中产生 α-肽。这种连接对 α-氨基腈偶联具有极高的选择性，并能耐受所有 20 个蛋白质氨基酸残基。两个基本特征使肽能够在水中连接：α-氨基腈的反应性和 pKaH 使它们与中性 pH 值的
• Chemoselectivity of chemically modified α-chymotrypsin
  作者：A. Dominguez、N. Cabezas、J.M. Sánchez - Montero、J.V. Sinisterra

  DOI：10.1016/0040-4020(94)01060-d

  日期：1995.2

  modified α-CT (α-CT-PEG) must be lower than 14.455 Å because the synthesis of peptides is not observed using 2-aminoethanol octanoate as nucleophile. α-CT-PEG is chemoselective towards the aromatic esters because unnatural aliphatic esters are not hydrolyzed in the presence of N-benzoyl-L-Tyrosine ethyl ester. Unnatural aliphatic acyl-donors with a distance smaller than 8.8 Å are recognized by the chemically

  讨论了用单甲氧基聚乙二醇（α-CT-PEG）化学修饰的α-胰凝乳蛋白酶的酶活性，该酶以不同于天然酶底物的酯水解和肽合成为测试反应。这些反应允许分析α-CT-PEG的“ ar”，“ h”，“ n”和“ am”亚位的尺寸。使用2-氨基乙醇酸酯和甘氨酸衍生物，我们已经证明，化学修饰的α-CT（α-CT-PEG）的“ n”亚位的深度必须小于14.455Å，因为未观察到肽的合成。 2-氨基乙醇辛酸酯作为亲核试剂。α-CT-PEG对芳族酯具有化学选择性，因为非天然脂族酯在N-苯甲酰基-L-酪氨酸乙酯存在下不会被水解。距离不自然的脂族酰基供体小于8.8的小分子被化学修饰的酶识别为酰基给体。从这些结果，我们可以得出结论，α-CT-PEG不必识别酰基供体分子中N-酰基的存在。酰基供体和亲核试剂中均存在庞大的烷基链，这会降低酯水解和肽合成过程中生物催化剂的酶促活性。
• Development of Amino Acids Functionalized SBA-15 for the Improvement of Protein Adsorption
  作者：Raquel Gutiérrez-Climente、Margaux Clavié、Jérémie Gouyon、Giang Ngo、Yoann Ladner、Pascal Etienne、Pascal Dumy、Pierre Martineau、Martine Pugnière、Catherine Perrin、Gilles Subra、Ahmad Mehdi

  DOI：10.3390/molecules26196085

  日期：——

  observed while the structural ones remained unchanged. The adsorption of the enzyme lysozyme (Lyz) onto the resulting functionalized [email protected] materials was evaluated at different pHs. The presence of different functional groups compared with bare SBA-15 showed better adsorption results, for example, 79.6 nmol of Lyz adsorbed per m2 of [email protected] compared with the 44.9 nmol/m2 of the bare SBA-15

  对于涉及与生物系统和生物分子相互作用的许多应用（例如，催化、分离、传感器设计、纳米科学或药物递送），有序介孔材料及其具有多个官能团的修饰具有广泛的科学兴趣。特别是，将酶固定在固体载体上对工业和合成化学具有很高的吸引力，因为它可以开发稳定且廉价的生物催化剂。在此背景下，我们开发了新型硅烷化氨基酸衍生物 (Si-AA-NH 2) 在生物相容性条件下固定在 SBA-15 材料上，避免使用有毒催化剂、溶剂或试剂。所得氨基酸功能化材料 () 通过 XRD、TGA、EA、Zeta 电位、氮吸附和 FT-IR 进行表征。观察到物理性质（例如电荷）的差异，而结构性质保持不变。在不同的 pH 值下评估了酶溶菌酶 (Lyz) 对所得官能化 [电子邮件保护] 材料的吸附。与裸SBA-15 相比，不同官能团的存在显示出更好的吸附结果，例如，与裸SBA-15的44.9 nmol/m 2相比，每m 2 [email protected]吸附了79
• 5(4H)-Oxazolinones as acyl donors in papain-catalyzed peptide fragment condensations
  作者：Byung Keun Hwang、Qu-Ming Gu、Charles J. Sih

  DOI：10.1016/0040-4039(94)85208-1

  日期：1994.4

  Papain, a thiol protease was shown to utilize 5(4H)-oxazolinones of peptides as acyl donors in peptide segment condensations. The effectiveness of this methodology is illustrated by the successful coupling of oxidized insulin B chain (30 residues) to angiotensin III (7 residues) in 59% yield.

  木瓜蛋白酶，一种硫醇蛋白酶，在肽段缩合中显示出利用5（4H）-恶唑啉酮作为酰基供体。该方法的有效性通过氧化胰岛素B链（30个残基）与血管紧张素III（7个残基）的成功偶联以59％的产率得以说明。
• [EN] PROCESSES FOR THE PREPARATION OF THALIDOMIDE<br/>[FR] PROCÉDÉS DE PRÉPARATION DE THALIDOMIDE
  申请人：CIPLA LTD

  公开号：WO2009083724A1

  公开（公告）日：2009-07-09

  The present invention provides a process for the preparation of thalidomide (I) comprising: i) reacting a compound of formula (II), where one of R represents -OH or -NH2 and the other of R represents -NH2 or -OH, respectively, with a phthaloylating agent in the presence of a base and a a non-polar organic solvent to obtain a phthaloyl derivative where R have the same meanings as above; and ii) dehydrating the phthaloyl derivative using a dehydrating agent selected from an acid anhydride, an acid halide, an ion exchange resin or a molecular sleve to obtain thalidomide (I).

  本发明提供了一种制备沙利度胺（I）的方法，包括：i）在碱和非极性有机溶剂存在下，将式（II）的化合物与邻苯二甲酰化试剂反应，其中R中的一个代表-OH或-NH2，另一个分别代表-NH2或-OH，以获得邻苯二甲酰衍生物，其中R具有与上述相同的含义；以及ii）使用选自酸酐、酸卤、离子交换树脂或分子筛的脱水试剂，脱水邻苯二甲酰衍生物，以获得沙利度胺（I）。