甘氨酰甘氨酰-L-组氨酸 | 7451-76-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 组氨酸类衍生物
• 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: 甘氨酰甘氨酰-L-组氨酸
• 英文名称: diglycylhistidine
• 英文别名: gly-gly-his；glycylglycylhistidine；2-[[2-[(2-azaniumylacetyl)amino]acetyl]amino]-3-(1H-imidazol-5-yl)propanoate
• CAS: 7451-76-5；93404-95-6
• 化学式: C₁₀H₁₅N₅O₄
• 分子量: 269.26
• InChiKey: PDAWDNVHMUKWJR-UHFFFAOYSA-N

物化性质

• 熔点：
  >210 °C (decomp)
• 沸点：
  813.8±65.0 °C(Predicted)
• 密度：
  1.440

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  150
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  potassium tetrachloropalladate(II) 、 甘氨酰甘氨酰-L-组氨酸 以 重水 为溶剂， 生成 [Pd(II)(gly-gly-his-2H)](1-)
  参考文献：
  名称：

  Coordination of Ru(NO)Cl3 to the tripeptides glyglygly and glyglyhis: N-terminal amine–amide and C-terminal imidazole–amide functionalities in bidentate chelation

  摘要：

  [RuCl3(NO)(H2O)(2)] (1) reacts with triglycine (gly-gly-gly) (***) and digtycylhistidine (gly-gly-his) (***) (*** symbols represent formulas of the peptides for the monoanion deprotonated at the carboxylate: (giy-gly-gly-H) or (gly-gly-his-H) represents ligands of one deprotonated amide, and (gly-gly-gly-2H) with two deprotonated amides) to form several complexes of the {Ru-II(NO+)}(6) chromophore. Only coordination from the terminal amino group of (gly-gly-gly) occurs below pH similar to 5. After heating 15h at 55 degreesC, pH 8.22, coordination through the terminal amine and adjacent ionized amido group as [Ru(NO)Cl-3(gly-gly-gly-H)](2-) (2) is detected by H-1 NMR with the appearance of one 'AB' quartet for the CH2 adjacent to the N-terminus. The NO stretching frequency suggests chelated Na-2[Ru(NO)Cl-3(gly-gly-gly-H)] (v(NO) = 1877 cm(-1)). Removal of 3Cl(-) by treatment with 3Ag(CF3CO2) at pH 7.6 allowed formation of the more chelated [Ru(NO)(H2O)(2)(gly-gly-gly-2H)] in approximately 56% yield, but the equilibrium could not be shifted Fully to this two-amide bound chelate. apparently due to competitive hydrolysis or increased lability of the [Ru(NO)(H2O)(3)](3+) center. The species that have been detected for gly-gly-his complexes (3) strongly depend upon the pH of the preparation. One main species and three lesser ones, in abundances of approximately 70, 20, and 10%, are produced in 3 h (55 degreesC) at pH 5.2. The major isomer is coordinated only via the imidazole side chain. Approximately 20% adopts the C-terminal imidazole plus the adjacent amide chelation. distributed between two diastereomers with the terminal carboxylate placed above or below the RuN2Cl2 plane in nearly equal amounts. Another 10% adopts the N-terminal amine plus amide chelation of the kind discussed for gly-gly-gly. The v(NO) value of 1871 cm (-1) of the main imidazole-only coordinated product matches that observed for the 1:1 [RuCl3(NO)(imidazole)(H2O)] complex. The dissociation of the imidazole-bound species occurs when the pH is raised above 8. The distribution of species and the nearly equal amounts of the diastereomers have been supported by MMFF94 and SYBYL molecular mechanics structural energy minimization calculations. [Ni-II(gly-gly-gly-2H)](2+) and [Pd-II(gly-gly-gly-2H)Cl](2-) were examined by NMR methods for comparison. The presence or absence of the coordinated carboxylate was readily established by C-k13 NMR spectroscopy via a carboxylate chemical shift near 187 ppm for Ni-II and 173 ppm for {Ru(NO)}(6) or Pd-II. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(00)00309-1

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
• SOLOMONAMIDE ANALOGUE COMPOUNDS, PHARMACEUTICALS CONTAINING SOLOMONAMIDE ANALOGUE COMPOUNDS, AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：US20150291659A1

  公开（公告）日：2015-10-15

  Solomanamide analogues of Formula-I having anti-inflammatory activity, and viable synthetic routes for the preparation of such analogues, including the synthesis of macrocyclic core of Salomanamide analogues. The Solomanamide analogues of Formula-I or their pharmaceutical salt may be provided in a pharmaceutical composition and administered in an effective amount for the treatment of inflammation and/or pain.

  公式I的Solomanamide类似物具有抗炎活性，并且具有制备这种类似物的可行合成路线，包括制备Salomanamide类似物的大环核心的合成。公式I的Solomanamide类似物或其药物盐可以在药物组合物中提供，并以有效剂量用于治疗炎症和/或疼痛。
• AGENT FOR SUPPRESSING TUMOUR GROWTH
  申请人：Institut Elementoorganicheskikh Soedineny Rossiiskoi Akademii Nauk (Ineos Ran)

  公开号：EP0786253A1

  公开（公告）日：1997-07-30

  The invention pertains to biology and medicine, specifically, to the suppression of malignant tumour growth. The problem addressed by the invention is that of finding more effective and less toxic agents for suppressing tumour growth. The invention in essence proposes the use of a substance consisting of a cobalt or iron complex with substituted phthalocyanines (I) or naphthalocyanines (II) and of a biogenic reducing agent. In the formulae shown, R = COONa, SO3Na, CH2C5H4N⊕Cl⊖, CH2(NH2)2S⊕CH2Cl⊖. Use of the proposed agent facilitates effective suppression of a wide range of malignant neoplasms, specifically, suppression of malignant cell proliferation (in vitro), slowing of tumour growth in mice (in vivo), and a significant increase in the life expectancy of the mice by comparison with inter alia the use of a prototype.

  本发明涉及生物学和医学，特别是抑制恶性肿瘤生长。本发明要解决的问题是找到更有效、毒性更小的抑制肿瘤生长的药物。本发明实质上提出使用一种物质，该物质由钴或铁与取代酞菁（I）或萘酞菁（II）的络合物和一种生物还原剂组成。在所示公式中，R = COONa、SO3Na、CH2C5H4N⊕Cl⊖、CH2(NH2)2S⊕CH2Cl⊖。使用该制剂可有效抑制多种恶性肿瘤，特别是抑制恶性细胞增殖（体外）、减缓肿瘤在小鼠体内的生长（体内），以及与使用原型制剂相比显著延长小鼠的寿命。
• Composition containing a penem or carbapenem antibiotic
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0226304B1

  公开（公告）日：1991-08-28
• Novel acylamino acid compounds and a method for their production
  申请人：NATIONAL FOOD RESEARCH INSTITUTE MINISTRY OF AGRICULTURE, FORESTRY AND FISHERIES

  公开号：EP0500332B1

  公开（公告）日：1998-05-27