N-acetylated L-histidylglycine | 23506-34-5

• 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: N-acetylated L-histidylglycine
• 英文别名: N-acetyl-L-histidylglycine；Ac-His-Gly；Ac-His-Gly-OH；Ac-L-His-Gly；N-(N^α-acetyl-histidyl)-glycine；N-Acetyl-L-histidyl-glycin；2-[[(2S)-2-acetamido-3-(1H-imidazol-5-yl)propanoyl]amino]acetic acid
• CAS: 23506-34-5
• 化学式: C₁₀H₁₄N₄O₄
• 分子量: 254.246
• InChiKey: DVGRJKALLKJPSI-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acetylated L-histidylglycine 在 C₁₄H₃₆N₆O₂Pt₂⁽⁴⁺⁾ 、 水 作用下， 反应 72.0h， 生成 N-乙酰-L-组氨酸
  参考文献：
  名称：

  各种吡嗪桥联的铂（II）配合物的合成，光谱和X射线表征：1 H NMR比较研究其催化甲硫氨酸和组氨酸二肽水解的能力

  摘要：

  摘要四种吡嗪（pz）桥连的Pt（II）配合物[{Pt（1,3-pd）Cl} 2（μ-pz）] Cl 2·LiCl（1）（1,3-pd = 1,3 -丙二胺），[{Pt（2,2-diMe-1,3-pd）Cl} 2（μ-pz）] Cl 2·2 [Li（H 2 O）4] Cl·2H 2 O（2） （2,2-diMe-1,3-pd = 2,2-二甲基-1,3-丙二胺），[{Pt（1,3-pnd）Cl} 2（μ-pz）]（ClO 4）2 ·H 2 O（3）（1,3-pnd =（±）-1,3-戊二胺）和[{Pt（1,3-pnd）Cl} 2（μ-pz）] Cl 2·2 [Pt合成了（1,3-pnd）Cl 2]·2H 2 O（4）。已经对化合物1-3进行了NMR和UV-Vis光谱表征，对配合物2和4进行了单晶X射线分析。4晶体中的原子分布表明存在一种无序现象，这可能归因于[{Pt（1,3-pnd）Cl} 2（μ-pz）]

  DOI：

  10.1016/j.poly.2016.06.011

文献信息

• New Selectivity and Turnover in Peptide Hydrolysis by Metal Complexes. A Palladium(II) Aqua Complex Catalyzes Cleavage of Peptides Next to the Histidine Residue
  作者：Tatjana N. Parac、Nenad M. Kostić

  DOI：10.1021/ja952162e

  日期：1996.1.1

  the palladium(II)−peptide complex. The cleavage is regioselective. In all the aforementioned dipeptides and in the tripeptide AcGly-His-Gly only the amide bond involving the carboxylic group of histidine is cleaved; the amide bond involving the amino group of histidine is not cleaved. When the carboxylic group of histidine is free, as in AcGly-His, cis-[Pd(en)(H2O)2]2+ does not effect hydrolysis. Lability

  这似乎是第一次报告称与组氨酸残基结合的过渡金属络合物会影响该残基旁边的肽的水解裂解。AcHis-Aa 二肽，其中 C 端氨基酸指定为 Aa 为 Gly、Ala、Ser、Thr、Leu、Phe 和 Tyr，在 60 °C 和 1.46 ≤ pD ≤ 2.61 下在 cis-[Pd (en)(H2O)2]2+。通过 1H NMR 光谱可以方便地监测反应，我们报告了动力学。就钯 (II)-肽复合物而言，该反应是单分子的。切割是区域选择性的。在所有上述二肽和三肽 AcGly-His-Gly 中，仅涉及组氨酸羧基的酰胺键断裂；涉及组氨酸氨基的酰胺键未裂解。当组氨酸的羧基游离时，如 AcGly-His，cis-[Pd(en)(H2O)2]2+ 不影响水解。钯 (II) 配合物和酸性溶液的不稳定性使得水解中的适度转变成为可能；催化剂...
• New Regioselectivity in the Cleavage of Histidine-Containing Peptides by Palladium(II) Complexes Studied by Kinetic Experiments and Molecular Dynamics Simulations
  作者：Tatjana N. Parac、G. Matthias Ullmann、Nenad M. Kostić

  DOI：10.1021/ja982369i

  日期：1999.4.1

  Palladium(II) complexes promote hydrolytic cleavage of amide bonds in N-acetylhistidylglycine (AcHis−Gly), N-acetylhistidine (AcHis), and their derivatives methylated at the N-1 or N-3 atom of imidazole. Methylation controls coordination of imidazole to palladium(II) and allows stereochemical analysis of the reactions. The complex [PdCl4]2- regioselectively cleaves the amide bond involving the carboxylic

  钯 (II) 复合物促进 N-乙酰组氨酰甘氨酸 (AcHis-Gly)、N-乙酰组氨酸 (AcHis) 及其衍生物中酰胺键的水解裂解，这些衍生物在咪唑的 N-1 或 N-3 原子处甲基化。甲基化控制咪唑与钯 (II) 的配位，并允许对反应进行立体化学分析。复合物 [PdCl4]2- 区域选择性地裂解涉及组氨酸羧基的酰胺键，即 His-Gly 键；当肽通过 N-1 和 N-3 原子与钯 (II) 配位时，裂解的速率常数几乎相同。复合物 [Pd(H2O)4]2+ 以相当的速率裂解涉及乙酰化二肽中组氨酸的羧基 (His-Gly) 和氨基 (AcHis) 的酰胺键。这种前所未有的反应性通过理论计算得到检验，其中以新的方式将分子动力学和泊松-玻尔兹曼方程的解结合起来。当 Pd(H2O)32+ 基团连接到 N-1 原子时，两个易裂键都可以通过 i...
• Copper(II) Binding Modes in the Prion Octapeptide PHGGGWGQ: A Spectroscopic and Voltammetric Study
  作者：Raffaele P. Bonomo、Giuseppe Impellizzeri、Giuseppe Pappalardo、Enrico Rizzarelli、Giovanni Tabbì

  DOI：10.1002/1521-3765(20001117)6:22<4195::aid-chem4195>3.0.co;2-2

  日期：2000.11.17

  absorption spectra suggest a similar co-ordination sphere of the metal ion in both peptides, which at neutral pH consists of a square pyramidal geometry with three peptidic nitrogens and the imidazole nitrogen as donor atoms. Cyclic voltammetric measurements were used to confirm the geometrical features of these copper(II) complexes: the observation of negative redox potentials are in good agreement with

  已知人类朊病毒蛋白 (PrPc) 的 N 端八肽重复区域与 Cu(II) 结合。为了研究铜在 PrPc 中的结合模式，合成了八肽 Ac-PHGGGWGQ-NH2 (1)，对应于八重重复序列，以及四肽 Ac-HGGG-NH2 (2)。已通过圆二色性 (CD) 和电子自旋共振 (ESR) 光谱研究了与 1 和 2 形成的铜 (II) 配合物。这两种肽在中性和碱性 pH 值下与 Cu(II) 形成 1:1 复合物。CD、ESR 和可见吸收光谱表明两种肽中金属离子的配位球相似，在中性 pH 值下由具有三个肽氮和咪唑氮作为供体原子的方形金字塔几何结构组成。循环伏安测量用于确认这些铜 (II) 配合物的几何特征：观察到的负氧化还原电位与推断的几何形状非常一致。所有这些结果综合起来表明，肽 1 提供了一个单一的金属结合位点，铜 (II) 在中性和碱性 pH 值下与该位点强烈结合，并且金属的结合诱导了 HGGG
• Disparate behavior of pyrazine and pyridazine platinum(II) dimers in the hydrolysis of histidine- and methionine-containing peptides and unique crystal structure of {[Pt(en)Cl]2(μ-pydz)}Cl2 with a pair of NH⋯Cl−⋯HN hydrogen bonds supporting the pyridazine bridge
  作者：Snežana Rajković、Urszula Rychlewska、Beata Warżajtis、Darko P. Ašanin、Marija D. Živković、Miloš I. Djuran

  DOI：10.1016/j.poly.2013.09.008

  日期：2014.1

  Treatment of [Pt(en)Cl-2] complex with pyridazine lead to the formation of new diplatinum(II) coordination compound [Pt(en)CIl(2)(mu-pydz))Cl-2, which was characterized by NMR spectroscopy and single-crystal X-ray diffraction. X-ray analysis revealed that the needed support for the pyridazine bridge formation, which in other metal complexes has been mostly provided by additional bridging units coordinated to metal centers, might come from supramolecular interactions such as intermolecular hydrogen bonds. This complex was converted into the corresponding aqua complex, [Pt(en)(H2O)](2)(mu-pydz))(4+), and 1H NMR spectroscopy was applied for comparison of its catalytic activity with that of the analogous pyrazine-bridged [Pt(en)(H2O)](2)(P-Pz))(4) complex in the hydrolysis of the N-acetylated L-histidylglycine (Ac-L-His-Gly) and L-methionyl-glycyl-L-histidyl-glycineamide (Ac-L-Met-Gly-L-His-GlyNH(2)). All reactions were performed in the pH range 2.0-2.5 and at 37 degrees C. It was found that although dimerization, in general, improves significantly the hydrolytic potency of Pt(II) complexes, the pyridazine Pt(II) dimer is significantly less active than its pyrazine Pt(II) analog, which is probably due to an increased steric effect exerted in the former complex by the ortho-position of the two nitrogen atoms. Consequently, [Pt(en)(H2O)](2)(mu-pydz))(4+) only binds to the methionine sulfur atom of the Ac-L-Met-Gly-L-His-GlyNFI(2) peptide and promotes cleavage of amide bond that involves the carboxylic group of methionine. In contrast, the analogous pyrazine Pt(II) dimer reacts with both methionine and histidine residues of this tetrapeptide, promoting cleavage of amide bonds involving carboxylic groups of both of these anchoring amino acids. Considering these results it can be assumed that in the polypeptide containing both methionine and histidine residues the regioselective cleavage of the amide bond involving only the carboxylic group of methionine can be achieved successfully by using the presently investigated pyridazine-bridged Pt(II) complex. (C) 2013 Elsevier Ltd. All rights reserved.
• Diethanolamine Pd(II) complexes in bioorganic modeling as model systems of metallopeptidases and soybean lipoxygenase inhibitors
  作者：Zorica D. Petrović、Dimitra Hadjipavlou-Litina、Eleni Pontiki、Dušica Simijonović、Vladimir P. Petrović

  DOI：10.1016/j.bioorg.2009.07.003

  日期：2009.10

  The reaction of PdCl2 with diethanolammonium chloride (DEAxHCl), in the molar ratio 1: 2, affords the [HDEA](2)[PdCl4] complex (1). The hydrolytic activity of the novel Pd(II) complex 1 was tested in reaction with N-acetylated L-histidylglycine dipeptide (AcHis-Gly). Complex 1, as well as earlier prepared trans[ PdCl2(DEA)(2)] complex (2), and DEA, as their precursor, were tested for their in vitro free radical scavenging activity. UV absorbance-based enzyme assays were done in order to evaluate their inhibitory activity of soybean lipoxygenase (LOX). Also, assays with superoxide anion radical were done. The scavenging activities of the complexes were measured and compared with those of their precursors and caffeic acid. Complex 2 exhibits the highest antioxidant activity and the highest inhibitory effect against the soybean LOX. (C) 2009 Elsevier Inc. All rights reserved.