methyl 2-[[(2S)-6-amino-2-(phenylmethoxycarbonylamino)hexanoyl]amino]acetate | 211797-31-8

• 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: methyl 2-[[(2S)-6-amino-2-(phenylmethoxycarbonylamino)hexanoyl]amino]acetate
• CAS: 211797-31-8
• 化学式: C₁₇H₂₅N₃O₅
• 分子量: 351.403
• InChiKey: BECWRFRUZOOHFK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[[(2S)-6-amino-2-(phenylmethoxycarbonylamino)hexanoyl]amino]acetate 在 sodium acetate 、 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 methyl 2-[[(2S)-6-(2,5-dioxopyrrol-1-yl)-2-(phenylmethoxycarbonylamino)hexanoyl]amino]acetate
  参考文献：
  名称：

  Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors

  摘要：

  A series of novel transglutaminase inhibitors was prepared, based on the scaffold of a commonly used peptide substrate and bearing an electrophilic maleimide group. These compounds were evaluated in vitro and shown to lead to irreversible inactivation of tissue transglutaminase. Comparison with inhibitors studied previously provides insight into the steric environment of the enzyme active site. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.061
• 作为产物：
  描述：

  Nε-Boc-Nα-Cbz-L-赖氨酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 methyl 2-[[(2S)-6-amino-2-(phenylmethoxycarbonylamino)hexanoyl]amino]acetate
  参考文献：
  名称：

  Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors

  摘要：

  A series of novel transglutaminase inhibitors was prepared, based on the scaffold of a commonly used peptide substrate and bearing an electrophilic maleimide group. These compounds were evaluated in vitro and shown to lead to irreversible inactivation of tissue transglutaminase. Comparison with inhibitors studied previously provides insight into the steric environment of the enzyme active site. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.061

文献信息

• Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors
  作者：Dany Halim、Karine Caron、Jeffrey W. Keillor

  DOI：10.1016/j.bmcl.2006.10.061

  日期：2007.1

  A series of novel transglutaminase inhibitors was prepared, based on the scaffold of a commonly used peptide substrate and bearing an electrophilic maleimide group. These compounds were evaluated in vitro and shown to lead to irreversible inactivation of tissue transglutaminase. Comparison with inhibitors studied previously provides insight into the steric environment of the enzyme active site. (c) 2006 Elsevier Ltd. All rights reserved.