cyclo(L-tyrosine(OBn)-glycine) | 1628630-12-5

• 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: cyclo(L-tyrosine(OBn)-glycine)
• 英文别名: (3S)-3-[(4-phenylmethoxyphenyl)methyl]piperazine-2,5-dione
• CAS: 1628630-12-5
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: ODKYNKZETZVCJN-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclo(L-tyrosine(OBn)-glycine) 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以92%的产率得到3-(S)-(4-hydroxy-benzyl)-piperazine-2,5-dione
  参考文献：
  名称：

  带有苄基部分的二酮哌嗪的合成和构象表征

  摘要：

  合成带有苄基部分和不同对位取代基的二酮哌嗪并通过 1 H NMR 光谱分析。发现所有这些二酮哌嗪都采用折叠的构形...

  DOI：

  10.1246/cl.131001
• 作为产物：
  描述：

  Boc-Tyr-Gly-OMe 在 甲酸 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 、 仲丁醇 为溶剂， 反应 68.0h， 生成 cyclo(L-tyrosine(OBn)-glycine)
  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

• Synthesis and Conformational Characterization of Diketopiperazines Bearing a Benzyl Moiety
  作者：Michiyasu Nakao、Yuriko Toriuchi、Shintaro Fukayama、Shigeki Sano

  DOI：10.1246/cl.131001

  日期：2014.3.5

  Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1H NMR spectroscopy. All of these diketopiperazines were found to adopt a folded conforma...

  合成带有苄基部分和不同对位取代基的二酮哌嗪并通过 1 H NMR 光谱分析。发现所有这些二酮哌嗪都采用折叠的构形...
• 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.