2-[[氨基-(膦酰氨基)亚甲基]氨基]乙酸 | 5115-19-5

• 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
• 中文名称: 2-[[氨基-(膦酰氨基)亚甲基]氨基]乙酸
• 英文名称: Phosphoglycocyamin
• 英文别名: Glykocyaminphosphorsaeure；phosphocreatine；N-phosphonocarbamimidoyl-glycine；N-Phosphonocarbamimidoyl-glycin；(N'-Phosphono-guanidino)-essigsaeure；Glykocyaminphosphonsaeure；Phosphoglykocyamin；Phosphoguanidinoacetate；2-[[amino-(phosphonoamino)methylidene]amino]acetic acid
• CAS: 5115-19-5
• 化学式: C₃H₈N₃O₅P
• 分子量: 197.087
• InChiKey: UUZLOPBEONRDRY-UHFFFAOYSA-N

物化性质

• 熔点：
  150 °C
• 沸点：
  474.5±47.0 °C(Predicted)
• 密度：
  2.09±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  aqueous cadmium chloride 、 2-[[氨基-(膦酰氨基)亚甲基]氨基]乙酸 以 甲醇 、 乙醇 为溶剂， 以49%的产率得到
  参考文献：
  名称：

  SYNTHESIS AND CHARACTERIZATION OF CADMIUM COMPLEXES WITH PHOSPHORYLATED LIGANDS

  摘要：

  Complexes of cadmium(II) with phosphorylated ligands were studied in the solid state. One of these ligands is phosphocreatine (HPCR), an important natural compound and the others are diisopropylphosphorylguanidine (DPG) and diisopropylphosphorylthiourea (DPT). The complexes were synthesized and characterized by elemental and thermogravimetric analyses and IR and Raman spectroscopy. The formed complexes are: [Cd(PCr)Cl](2), Cd(DPG)Cl-2 and [Cd(DPT)(3)Cl]Cl. In the HPCR and DPG complexes, Cd(II) is bound through the oxygen of the phosphoryl group and the nitrogen of the guanidine group and in the DPT complexes through the sulfur atom.

  DOI：

  10.1081/sim-100002236
• 作为产物：
  描述：

  胍基乙酸 在 pyruvate kinase 、 recombinant mitochondrial taurocyamine kinase from Arenicola brasiliensis 、 potassium chloride 、 magnesium acetate 、 2-(膦酰氧基)丙烯酸酯 、 5’-三磷酸腺苷 、 还原型辅酶Ⅰ 、 L-lactate dehydrogenase 作用下， 生成 2-[[氨基-(膦酰氨基)亚甲基]氨基]乙酸
  参考文献：
  名称：

  Identification of amino acid residues responsible for taurocyamine binding in mitochondrial taurocyamine kinase from Arenicola brasiliensis

  摘要：

  In order to investigate the residues associated with binding of the substrate taurocyamine in Arenicola mitochondrial taurocyamine kinase (TK), we performed Ala-scanning of the amino acid sequence HTKTV at positions 67-71 on the GS loop, and determined apparent K(m) and V(max) (appK(m) and appV(max), respectively) of the mutant forms for the substrates taurocyamine and glycocyamine. The appK(m) values for taurocyamine of the K69A, T70A and V71A mutants were significantly increased as compared with wild-type, suggesting that these residues are associated with taurocyamine binding. Of special interest is a property of V71A mutant: its catalytic efficiency for glycocyamine was twice that for taurocyamine, indicating that the V71A mutant acts like a glycocyamine kinase, rather than a TK. The role of the amino acid residue K95 of Arenicola MiTK was also examined. K95 was replaced with R, H. V. I. A and E. K95R, K95H and K95I have a 3-fold higher affinity for taurocyamine, and activity was largely lost in K95E. On the other hand, the K95Y mutant showed a rather unique feature: namely, an increase in substrate concentration caused a decrease in initial velocity of the reaction (substrate inhibition). This is the first report on the key amino acid residues responsible for taurocyamine binding in mitochondrial TK. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbapap.2011.06.003

文献信息

• Cramer,F. et al., Chemische Berichte, 1962, vol. 95, p. 1670 - 1682
  作者：Cramer,F. et al.

  DOI：——

  日期：——
• Effect of Betula pendula Admixture on Tree Growth and Branch Diameter in young Pinus sylvestris Stands in Southern Finland
  作者：Sauli Valkonen、Juha Ruuska

  DOI：10.1080/713711863

  日期：2003.9.1
• Fawaz; Seraidarian, Journal of Biological Chemistry, 1946, vol. 165, p. 100
  作者：Fawaz、Seraidarian

  DOI：——

  日期：——
• Identification of amino acid residues responsible for taurocyamine binding in mitochondrial taurocyamine kinase from Arenicola brasiliensis
  作者：Kumiko Tanaka、Tamotsu Matsumoto、Tomohiko Suzuki

  DOI：10.1016/j.bbapap.2011.06.003

  日期：2011.10

  In order to investigate the residues associated with binding of the substrate taurocyamine in Arenicola mitochondrial taurocyamine kinase (TK), we performed Ala-scanning of the amino acid sequence HTKTV at positions 67-71 on the GS loop, and determined apparent K(m) and V(max) (appK(m) and appV(max), respectively) of the mutant forms for the substrates taurocyamine and glycocyamine. The appK(m) values for taurocyamine of the K69A, T70A and V71A mutants were significantly increased as compared with wild-type, suggesting that these residues are associated with taurocyamine binding. Of special interest is a property of V71A mutant: its catalytic efficiency for glycocyamine was twice that for taurocyamine, indicating that the V71A mutant acts like a glycocyamine kinase, rather than a TK. The role of the amino acid residue K95 of Arenicola MiTK was also examined. K95 was replaced with R, H. V. I. A and E. K95R, K95H and K95I have a 3-fold higher affinity for taurocyamine, and activity was largely lost in K95E. On the other hand, the K95Y mutant showed a rather unique feature: namely, an increase in substrate concentration caused a decrease in initial velocity of the reaction (substrate inhibition). This is the first report on the key amino acid residues responsible for taurocyamine binding in mitochondrial TK. (C) 2011 Elsevier B.V. All rights reserved.
• SYNTHESIS AND CHARACTERIZATION OF CADMIUM COMPLEXES WITH PHOSPHORYLATED LIGANDS
  作者：Judith Felcman、Damiana C. N. Lopes、Renata A. Cattapan、Claudio A. Téllez Soto

  DOI：10.1081/sim-100002236

  日期：2001.3.31

  Complexes of cadmium(II) with phosphorylated ligands were studied in the solid state. One of these ligands is phosphocreatine (HPCR), an important natural compound and the others are diisopropylphosphorylguanidine (DPG) and diisopropylphosphorylthiourea (DPT). The complexes were synthesized and characterized by elemental and thermogravimetric analyses and IR and Raman spectroscopy. The formed complexes are: [Cd(PCr)Cl](2), Cd(DPG)Cl-2 and [Cd(DPT)(3)Cl]Cl. In the HPCR and DPG complexes, Cd(II) is bound through the oxygen of the phosphoryl group and the nitrogen of the guanidine group and in the DPT complexes through the sulfur atom.