glutamate

• 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: glutamate
• 英文别名: Glu；L-glutamate；2-azaniumylpentanedioate
• 化学式: C₅H₈NO₄
• 分子量: 146.123
• InChiKey: WHUUTDBJXJRKMK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-dimethylamino-4-hydroxybiphenyl-3-carbaldehyde 、 glutamate 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Salicyaldehyde-based fluorescent sensors with high sensitivity for amino acids

  摘要：

  Structurally simple salicylaldehyde-based fluorescent sensors for amino acids have been obtained by one-step or two-step synthesis. These sensors show significant fluorescence enhancement in the presence of many amino acids at concentrations as low as 10(-5) mol/L. The reversible reaction of the aldehydes with amino acids to form imines in aqueous solution is proposed to account for the observed fluorescence enhancement. (C) 2011 Xi Huai Qiang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.03.005
• 作为产物：
  描述：

  DL-脯氨酸 在 Bradyrhizobium japonicum Proline utilization A 、 3-(aminocarbonyl)-1-[5-O-[[1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranos-5-O-yl]phosphonyloxy(oxylato)phosphinyl]-β-L-ribofuranosyl]pyridinium 作用下， 以 aq. phosphate buffer 为溶剂， 生成 glutamate
  参考文献：
  名称：

  Kinetic and Structural Characterization of Tunnel-Perturbing Mutants in Bradyrhizobium japonicum Proline Utilization A

  摘要：

  Proline utilization A from Bradyrhizobium japonicum (BjPutA) is a bifunctional flavoenzyme that catalyzes the oxidation of proline to glutamate using fused proline dehydrogenase (PRODH) and Delta(1)-pyrroline-5-carboxylate dehydrogenase (PSCDH) domains. Recent crystal structures and kinetic data suggest an intramolecular channel connects the two active sites, promoting substrate channeling of the intermediate Delta(1)-pyrroline-5-carboxylate/glutamate-gamma-semialdehyde (PSC/GSA). In this work, the structure of the channel was explored by inserting large side chain residues at four positions along the channel in BjPutA. Kinetic analysis of the different mutants revealed replacement of D779 with Tyr (D779Y) or Trp (D779W) significantly decreased the overall rate of the PRODH-PSCDH channeling reaction. X-ray crystal structures of D779Y and D779W revealed that the large side chains caused a constriction in the central section of the tunnel, thus likely impeding the travel of PSC/GSA in the channel. The D779Y and D779W mutants have PRODH activity similar to that of wild-type BjPutA but exhibit significantly lower PSCDH activity, suggesting that exogenous PSC/GSA enters the channel upstream of Asp779. Replacement of nearby Asp778 with Tyr (D778Y) did not impact BjPutA channeling activity. Consistent with the kinetic results, the X-ray crystal structure of D778Y shows that the main channel pathway is not impacted; however, an off-cavity pathway is closed off from the channel. These findings provide evidence that the off-cavity pathway is not essential for substrate channeling in BjPutA.

  DOI：

  10.1021/bi5007404

文献信息

• A prebiotic Krebs cycle analog generates amino acids with H2 and NH3 over nickel
  作者：Harpreet Kaur、Sophia A. Rauscher、Emilie Werner、Youngdong Song、Jing Yi、Wahnyalo Kazöne、William F. Martin、Harun Tüysüz、Joseph Moran

  DOI：10.1016/j.chempr.2024.02.001

  日期：2024.5

  nonenzymatic reductive amination of six biological ketoacids and glyoxylate to give the corresponding amino acids in good yields using ammonium concentrations ranging from 6 to 150 mM. Catalytic amounts of nickel or ground meteorites enable these reactions at 22°C and pH 8. The same conditions promote an H-dependent ketoacid-forming reductive aldol chemistry that co-occurs with reductive amination, producing

  大约 40 亿年来，氢 (H) 一直为微生物的新陈代谢提供动力。最近的发现还发现，它还为最古老的生物碳固定途径的地球化学类似物提供了燃料，这揭示了新陈代谢的起源。然而，目前尚不清楚H是否可以维持更复杂的非酶反应网络。在这里，我们表明，使用 6 至 150 mM 的铵浓度，H 驱动六种生物酮酸和乙醛酸的非酶还原胺化，以良好的产率产生相应的氨基酸。催化量的镍或磨碎的陨石在 22°C 和 pH 8 下能够实现这些反应。相同的条件促进 H 依赖性酮酸形成还原羟醛化学，该化学与还原胺化同时发生，产生类似于氨基酸合成的连续反应网络古代微生物的代谢核心。这些结果支持了这样的假设：最早的生化网络可能在没有酶或 RNA 的情况下出现。