2-fluorodehydrocoelenterazine

• 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: 2-fluorodehydrocoelenterazine
• 英文别名: (2Z)-8-benzyl-2-[(2-fluorophenyl)methylidene]-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3-one
• 化学式: C₂₆H₁₈FN₃O₂
• 分子量: 423.446
• InChiKey: XGLFGCIJNDZTGK-HAHDFKILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  65.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-fluorodehydrocoelenterazine 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 2.0h， 生成 N-[3-Benzyl-5-(4-hydroxy-phenyl)-pyrazin-2-yl]-2-((2S,3S)-2,3-dihydroxy-4-mercapto-butylsulfanyl)-2-(2-fluoro-phenyl)-acetamide
  参考文献：
  名称：

  19F-Dehydrocoelenterazine as probe to investigate the active site of symplectin

  摘要：

  Fluorinated dehydrocoelenterazines (F-DCTs) were synthesized to study molecular mechanisms of symplectin; a photoprotein of luminous squid Symplectoteuthis oualaniensis L. F-DCTs reacted with dithiothreitol and glutathione under neutral conditions to give the stable chromophores as symplectin model. Reconstructed symplectin was also obtained by addition of F-DCTs into apo-symplectin, and showed bioluminescence to emit 50-65% amount of light as natural symplectin. The structure of the chromophores was determined by F-19 NMR, Q-TOF-MS, and MS/MS analyses. Sequencing of the chromopeptides of symplectin models prepared from F-DCTs and thiol compounds was accomplished by ESI-Q-TOF-MS/MS analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00100-x
• 作为产物：
  描述：

  2-氟苯乙酸 在 盐酸 、 manganese(IV) oxide 、 sodium hydroxide 、 氯化亚砜 、 硫酸 、 氢溴酸 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 10.5h， 生成 2-fluorodehydrocoelenterazine
  参考文献：
  名称：

  19F-Dehydrocoelenterazine as probe to investigate the active site of symplectin

  摘要：

  Fluorinated dehydrocoelenterazines (F-DCTs) were synthesized to study molecular mechanisms of symplectin; a photoprotein of luminous squid Symplectoteuthis oualaniensis L. F-DCTs reacted with dithiothreitol and glutathione under neutral conditions to give the stable chromophores as symplectin model. Reconstructed symplectin was also obtained by addition of F-DCTs into apo-symplectin, and showed bioluminescence to emit 50-65% amount of light as natural symplectin. The structure of the chromophores was determined by F-19 NMR, Q-TOF-MS, and MS/MS analyses. Sequencing of the chromopeptides of symplectin models prepared from F-DCTs and thiol compounds was accomplished by ESI-Q-TOF-MS/MS analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00100-x

文献信息

• 19F-Dehydrocoelenterazine as probe to investigate the active site of symplectin
  作者：Minoru Isobe、Tatsuya Fujii、Masaki Kuse、Keiichi Miyamoto、Kazushi Koga

  DOI：10.1016/s0040-4020(02)00100-x

  日期：2002.3

  Fluorinated dehydrocoelenterazines (F-DCTs) were synthesized to study molecular mechanisms of symplectin; a photoprotein of luminous squid Symplectoteuthis oualaniensis L. F-DCTs reacted with dithiothreitol and glutathione under neutral conditions to give the stable chromophores as symplectin model. Reconstructed symplectin was also obtained by addition of F-DCTs into apo-symplectin, and showed bioluminescence to emit 50-65% amount of light as natural symplectin. The structure of the chromophores was determined by F-19 NMR, Q-TOF-MS, and MS/MS analyses. Sequencing of the chromopeptides of symplectin models prepared from F-DCTs and thiol compounds was accomplished by ESI-Q-TOF-MS/MS analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.