dehydrocoelenterazine mono-methyl ether | 276879-70-0

• 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: dehydrocoelenterazine mono-methyl ether
• 英文别名: (2Z)-8-benzyl-6-(4-hydroxyphenyl)-2-[(4-methoxyphenyl)methylidene]imidazo[1,2-a]pyrazin-3-one
• CAS: 276879-70-0
• 化学式: C₂₇H₂₁N₃O₃
• 分子量: 435.482
• InChiKey: XNLZLQHXFKEZIJ-JLPGSUDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dehydrocoelenterazine mono-methyl ether 在 potassium tert-butylate 、 氧气 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Synthesis of 13C-Dehydrocoelenterazine and NMR Studies on the Bioluminescence of a Symplectoteuthis Model

  摘要：

  The bioluminescence of luminous squid (Symplectoteuthis oualaniensis) is presumed to be initiated by the addition of the sulfhydryl residue of a photoprotein to dehydrocoelenterazine (DCL). To clarify this step, a novel synthetic route was established to label DCL with C-13. Dithiothreitol (DTT) and glutathione (GSH) were used as photoprotein models. The addition of DTT and GSH to C-13-labeled DCL gave luminous chromophores. Its structures were confirmed by NMR and MS spectrometry. The DTT adduct emitted light under alkaline condition to produce an oxidized compound. Thus we succeeded in modeling the bioluminescence of a photoprotein with DTT. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00163-0
• 作为产物：
  描述：

  4-(5-氨基-6-苄基吡嗪-2-基)苯酚 在 盐酸 、 manganese(IV) oxide 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 水 为溶剂， 反应 4.5h， 生成 dehydrocoelenterazine mono-methyl ether
  参考文献：
  名称：

  Synthesis of 13C-Dehydrocoelenterazine and NMR Studies on the Bioluminescence of a Symplectoteuthis Model

  摘要：

  The bioluminescence of luminous squid (Symplectoteuthis oualaniensis) is presumed to be initiated by the addition of the sulfhydryl residue of a photoprotein to dehydrocoelenterazine (DCL). To clarify this step, a novel synthetic route was established to label DCL with C-13. Dithiothreitol (DTT) and glutathione (GSH) were used as photoprotein models. The addition of DTT and GSH to C-13-labeled DCL gave luminous chromophores. Its structures were confirmed by NMR and MS spectrometry. The DTT adduct emitted light under alkaline condition to produce an oxidized compound. Thus we succeeded in modeling the bioluminescence of a photoprotein with DTT. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00163-0

文献信息

• Synthesis of 13C-Dehydrocoelenterazine and NMR Studies on the Bioluminescence of a Symplectoteuthis Model
  作者：Masaki Kuse、Minoru Isobe

  DOI：10.1016/s0040-4020(00)00163-0

  日期：2000.4

  The bioluminescence of luminous squid (Symplectoteuthis oualaniensis) is presumed to be initiated by the addition of the sulfhydryl residue of a photoprotein to dehydrocoelenterazine (DCL). To clarify this step, a novel synthetic route was established to label DCL with C-13. Dithiothreitol (DTT) and glutathione (GSH) were used as photoprotein models. The addition of DTT and GSH to C-13-labeled DCL gave luminous chromophores. Its structures were confirmed by NMR and MS spectrometry. The DTT adduct emitted light under alkaline condition to produce an oxidized compound. Thus we succeeded in modeling the bioluminescence of a photoprotein with DTT. (C) 2000 Elsevier Science Ltd. All rights reserved.