cyclo(L-tyrosine-3-methyl-L-tyrosine)

• 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: cyclo(L-tyrosine-3-methyl-L-tyrosine)
• 英文别名: (3~{S},6~{S})-3-[(4-hydroxyphenyl)methyl]-6-[(3-methyl-4-oxidanyl-phenyl)methyl]piperazine-2,5-dione；(3S,6S)-3-[(4-hydroxy-3-methylphenyl)methyl]-6-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: YBIHVNADQSTKMY-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基-4-羟基苯甲醛 在 ammonium hydroxide 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 16.25h， 生成 cyclo(L-tyrosine-3-methyl-L-tyrosine)
  参考文献：
  名称：

  Structure–Activity Relationships of cyclo(l-Tyrosyl-l-tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct

  摘要：

  A series of analogues of cyclo(L-tyrosyl-L-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been synthesized and analyzed by UV-vis and electron paramagnetic resonance spectroscopy and by X-ray crystallography. The introduction of iodine substituents onto cyclo(L-tyrosyl-L-tyrosine) results in sub-mu M binding affinity for the CYP121 enzyme and a complete shift to the high-spin state of the heme Fe-III. The introduction of halogens that are able to interact with heme groups is thus a feasible approach to the development of next-generation, tight binding inhibitors of the CYP121 enzyme, in the search for novel antitubercular compounds.

  DOI：

  10.1021/acs.jmedchem.9b01199

文献信息

• Structure–Activity Relationships of <i>cyclo</i>(<scp>l</scp>-Tyrosyl-<scp>l</scp>-tyrosine) Derivatives Binding to <i>Mycobacterium tuberculosis</i> CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct
  作者：Sunnia Rajput、Kirsty J. McLean、Harshwardhan Poddar、Irwin R. Selvam、Gayathri Nagalingam、James A. Triccas、Colin W. Levy、Andrew W. Munro、Craig A. Hutton

  DOI：10.1021/acs.jmedchem.9b01199

  日期：2019.11.14

  A series of analogues of cyclo(L-tyrosyl-L-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been synthesized and analyzed by UV-vis and electron paramagnetic resonance spectroscopy and by X-ray crystallography. The introduction of iodine substituents onto cyclo(L-tyrosyl-L-tyrosine) results in sub-mu M binding affinity for the CYP121 enzyme and a complete shift to the high-spin state of the heme Fe-III. The introduction of halogens that are able to interact with heme groups is thus a feasible approach to the development of next-generation, tight binding inhibitors of the CYP121 enzyme, in the search for novel antitubercular compounds.