L-glutamic acid diamide | 2013-17-4

• 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
• 英文名称: L-glutamic acid diamide
• 英文别名: L-glutamine amide；L-glutaminamide；glutamine amide；H-Gln-NH2；Gln-NH₂；Q-NH2；Glutamamide；(2S)-2-aminopentanediamide
• CAS: 2013-17-4
• 化学式: C₅H₁₁N₃O₂
• 分子量: 145.161
• InChiKey: LCGISIDBXHGCDW-VKHMYHEASA-N

物化性质

• 沸点：
  473.7±40.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 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：
  112
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  L-glutamic acid diamide 在 盐酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Structure activity studies on the C-terminal hexapeptide of substance P with modifications at the glutaminyl and methioninyl residues

  摘要：

  Analogues of [Orn6]-SP6-11 have been synthesized in which the SCH3 group of the Met11 side chain is replaced by other functional groups, such as (CH2)2NH2, COOH, CONH2, and COOR, which have basic, acid, or neutral character and which may act as either H-bonding donors or H-bonding acceptors. These analogues were tested in guinea pig ileum and rat colon muscularis mucosae, in vitro. Substitution of Lys, Gln, or Glu at position 11 caused a marked reduction in biological activity in both tissues. In contrast, the glutamate benzyl ester analogue had only slightly reduced activity in the guinea pig ileum and an increased (4.7 times) activity in the rat colon. It is concluded that charged groups in the side chain at position 11 of SP6-11 reduce the biological activity of SP hexapeptide.

  DOI：

  10.1021/jm00391a041
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 钯 作用下， 生成 L-glutamic acid diamide
  参考文献：
  名称：

  Dekker; Stone; Fruton, Journal of Biological Chemistry, 1949, vol. 181, p. 722,727

  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
• Method for treatment or prophylaxis of gastro-intestinal disease
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US04529602A1

  公开（公告）日：1985-07-16

  A method for the therapeutic treatment and/or prophylaxis of gastro-intestinal diseases using a sulfodehydroabietic acid of the formula: ##STR1## or a pharmaceutically acceptable salt thereof is disclosed.

  本发明涉及使用下式的磺化脱氢松香酸或其药学上可接受的盐进行治疗和/或预防胃肠疾病的方法：##STR1##
• THERMORESPONSIVE POLYMER AND PRODUCTION METHOD THEREOF
  申请人：NAGAOKA Hirokazu

  公开号：US20070203313A1

  公开（公告）日：2007-08-30

  A material which expresses its critical solution temperature even in an aqueous solution containing a buffer or salt, and at the same time, shows small variation width of the critical solution temperature even when concentration of salt or the like contained in water, a buffer liquid or the like is different, interacts with a substance such as a component in the living body and can therefore be used efficiently in the isolation of substances, is provided. A monomer represented by a formula (1) and a thermoresponsive polymer which contains said monomer as a polymerization component.

  提供一种材料，即使在含有缓冲液或盐的水溶液中也能表达其临界溶液温度，并且在水、缓冲液或类似物中含有盐等物质的浓度不同时，其临界溶液温度变化范围很小，与生物体中的组分等物质发生相互作用，因此在物质的分离中可以高效使用。该材料包括由式（1）表示的单体和包含该单体作为聚合组分的热敏聚合物。
• Thermoresponsive polymer and production method thereof
  申请人：Chisso Corporation

  公开号：US07847047B2

  公开（公告）日：2010-12-07

  A material which expresses its critical solution temperature even in an aqueous solution containing a buffer or salt, and at the same time, shows small variation width of the critical solution temperature even when concentration of salt or the like contained in water, a buffer liquid or the like is different, interacts with a substance such as a component in the living body and can therefore be used efficiently in the isolation of substances, is provided. A monomer represented by a formula (1) and a thermoresponsive polymer which contains said monomer as a polymerization component.

  提供一种物质，即使在含有缓冲剂或盐的水溶液中也能表达其临界溶解温度，并且在水，缓冲液或类似物中含有盐或类似物的浓度不同时，临界溶解温度的变化范围也很小，与生物体内的成分等物质相互作用，因此可以在物质的分离中高效使用。该物质包括一个由公式（1）表示的单体和含有该单体作为聚合组分的热响应性聚合物。
• Prebiotic Catalytic Peptide Ligation Yields Proteinogenic Peptides by Intramolecular Amide Catalyzed Hydrolysis Facilitating Regioselective Lysine Ligation in Neutral Water
  作者：Jyoti Singh、Daniel Whitaker、Benjamin Thoma、Saidul Islam、Callum S. Foden、Abil E. Aliev、Tom D. Sheppard、Matthew W. Powner

  DOI：10.1021/jacs.2c03486

  日期：2022.6.15

  understanding the emergence of life. Building on our recent discovery that thiols catalyze the ligation of amino acids, amides, and peptides with amidonitriles in neutral water, we demonstrate the outcome of ligation depends on pH and that high pKa primary thiols are the ideal catalysts. While the most rapid thiol catalyzed peptide ligation occurs at pH 8.5–9, the most selective peptide ligation, that

  催化剂控制的肽合成的益生元起源是理解生命出现的基础。基于我们最近发现的硫醇在中性水中催化氨基酸、酰胺和肽与酰胺腈的连接，我们证明连接的结果取决于 pH 值和高 p K a伯硫醇是理想的催化剂。虽然最快的硫醇催化肽连接发生在 pH 8.5–9，但最具选择性的肽连接，耐受所有蛋白质侧链，发生在 pH 7。我们还确定了中间肽基脒水解成的高度选择性机制α-肽虽然证明具有非蛋白质结构的脒（如 β-和 γ-肽）的水解显示出较差的选择性。值得注意的是，这一发现能够使赖氨酸肽在中性 pH 值下进行高度 α 选择性的无保护基连接，同时保持功能性 ε-胺侧链完整。