N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)methionine | 252909-87-8

• 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-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)methionine
• 英文别名: N-2-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidinyl)-L-methionine；(2S)-2-[(4-amino-1-methyl-5-nitroso-6-oxopyrimidin-2-yl)amino]-4-methylsulfanylbutanoic acid
• CAS: 252909-87-8
• 化学式: C₁₀H₁₅N₅O₄S
• 分子量: 301.326
• InChiKey: KSOORLDVGXYMHS-YFKPBYRVSA-N

物化性质

• 沸点：
  470.9±55.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  163
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cadmium(II) chloride 、 N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)methionine 在 KOH 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Solution study and 2-D layered structures of zinc(II) and cadmium(II) complexes with N-2-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidinyl)-l-methionine as ligand

  摘要：

  The solution study of the N-2-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidinyl)-L-methionine has revealed that it acts as a monoprotic acid in the pH range 2.5-9.5. In solution the complexes detected with Zn(II) and Cd(II) at 1:1 and 1:4 metal-to-ligand molar ratios were the mononuclear species [ZnL2], [CdL2] and [Cd(HL)](2+), with the ligand coordinating through the carboxylate group in the two former and through the pyrimidine ring in the later. From these, two layered complexes of Zn(II) and Cd(II) with HL were obtained. ([Zn(mu -L)(2)]. 2H(2)O)(n), monoclinic, space group P2(1), a = 10.882(3), b = 7.473(2), c = 18.534(4) Angstrom, beta = 90.92(2)degrees, Z = 2; ([Cd(mu -L)(2)]. 3H(2)O)(n), triclinic, space group P1, a = 7.615(2), b = 10.427(2), c = 11.129(2) Angstrom, alpha = 86.29(3), beta = 78.87(3), gamma = 71.13(3)degrees, Z = 1. The structures of both complexes are very similar except for the coordination numbers of five and seven for Zn(II) and Cd(II), respectively. These facts point out the versatility of this family of N-pyrimidine amino acids as ligands, as well as the importance of the crystallization processes in obtaining supramolecular compounds. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(00)00206-1
• 作为产物：
  描述：

  L-蛋氨酸 、 6-amino-3,4-dihydro-3-methyl-2-methoxy-5-nitroso-4-oxopyrimidine 在 氢氧化钾 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以75%的产率得到N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)methionine
  参考文献：
  名称：

  N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)methionine

  摘要：

  The absolute configuration of the title compound, C10H15N5O4S, has been determined and is in agreement with that of the starting material, L-methionine. Two identical hydrogen-bonded buckled sheets run parallel to the [101] and [(1) over bar 01] planes. Molecules lying in either of these planes are linked together by a ring structure to form these sheets, in which two chains of molecules run antiparallel to each other along the b axis. A further hydrogen-bonded ring structure links the [10 (1) over bar] and [101] sheets together, resulting in an infinite three-dimensional hydrogen-bonded network.

  DOI：

  10.1107/s0108270199008495

文献信息

• Bifunctional pyrimidine-amino-acid ligands: solution study and crystal structure of a Mn(II) chain alternating six- and sevenfold coordination environments
  作者：R López-Garzón、P Arranz-Mascarós、M.L Godino-Salido、M.D Gutiérrez-Valero、R Cuesta、J.M Moreno

  DOI：10.1016/s0020-1693(03)00343-8

  日期：2003.11

  The acid-base characterization in aqueous solution of the N-2-[4-amino-1,6-dihydro-1-methyl-5-nitroso-6-oxopyrimidinyl)methionine, a member of a family of bifunctional N-pyrimidine alpha-amino acids ligands, has been carried out by potentiometric and UV-Vis techniques in the 2.5-9.0 pH range, indicating a quasi-zwitterionic structure. The solution study of the HL/Mn(II) system at 1:2, 2:1 and 4:1 molar ratios (25 degreesC and pH < 6), reveals that both moieties are active in coordinating to the metal ion, through the carboxylate group when the ligand is deprotonated or through the pyrimidinic fragment when acting in its molecular form. A solid complex with MnL2.61/2H(2)O stoichiometry was isolated from an aqueous 1:3 [HL]/[Mn(II)] mixture at pH 6. The X-ray single-crystal characterization has revealed that this complex can be formulated as [Mn(H2O)(4)(mu-L)(2)Mn(L)(2)(H2O)].8H(2)O}(n), an infinite chain in which two different Mn(II) ions having six- and sevenfold coordination environments alternate along the chain. The asymmetric unit contains two ligands coordinating in different fashion. One of these coordinates monodentately through the oxygen atom belonging to the exocyclic nitroso group while the other exhibits a (3)eta-bridging pattern between the six- and sevenfold Mn(II) arrangements. The versatile coordination modes of this ligand is discussed and compared to other complexes of this bifunctional family of ligands. (C) 2003 Elsevier B.V. All rights reserved.