(S)-2-peroxycoelenterazine | 1161931-09-4

• 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: (S)-2-peroxycoelenterazine
• 英文别名: coelenterazine hydroperoxide；c2-Hydroperoxy-coelenterazine；(2S)-8-benzyl-2-hydroperoxy-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]imidazo[1,2-a]pyrazin-3-one
• CAS: 1161931-09-4
• 化学式: C₂₆H₂₁N₃O₅
• 分子量: 455.47
• InChiKey: HOSWCJDTHOAORT-SANMLTNESA-N

物化性质

• 沸点：
  726.4±70.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-peroxycoelenterazine 在 1,4-dithio-D,L-threitol 、 apoaequorin 、 氧气 、 三羟甲基氨基甲烷盐酸盐 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Selective protein modification by the hydroperoxide intermediate in a photoprotein, aequorin

  摘要：

  During the course of protein modi. cation program, we employed a recombinant aequorin, the apo-protein reconstituted with coelenterazine, and found out that the photolytic hyperperoxide modified three S-SCH2CHOHCHOHCH2SH groups to -S-SCH2CHOHCH = CH-S = O) H or -S-SCH2CHOHCH = CH-S(= O)OH of terminal DTT connected to cysteine residues of the C-145, C-152 and C-180, which turned out to locate near the chromophore. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.033
• 作为产物：
  描述：

  腔肠素 在 1,4-dithio-D,L-threitol 、 apoaequorin 、 氧气 、 三羟甲基氨基甲烷盐酸盐 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 (S)-2-peroxycoelenterazine
  参考文献：
  名称：

  Selective protein modification by the hydroperoxide intermediate in a photoprotein, aequorin

  摘要：

  During the course of protein modi. cation program, we employed a recombinant aequorin, the apo-protein reconstituted with coelenterazine, and found out that the photolytic hyperperoxide modified three S-SCH2CHOHCHOHCH2SH groups to -S-SCH2CHOHCH = CH-S = O) H or -S-SCH2CHOHCH = CH-S(= O)OH of terminal DTT connected to cysteine residues of the C-145, C-152 and C-180, which turned out to locate near the chromophore. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.033

文献信息

• Formation of Coelenteramine from 2‐Peroxycoelenterazine in the Ca ²⁺ ‐Binding Photoprotein Aequorin
  作者：Satoshi Inouye、Mitsuhiro Nakamura、Takamitsu Hosoya

  DOI：10.1111/php.13590

  日期：2022.9

  Aequorin consists of apoprotein (apoAequorin) and (S)-2-peroxycoelenterazine (CTZ-OOH) and is considered to be a transient-state complex of an enzyme (apoAequorin) and a substrate (coelenterazine and molecular oxygen) in the enzymatic reaction. The degradation process of CTZ-OOH in aequorin was characterized under various conditions of protein denaturation. By acid treatment, the major product from

  水母发光蛋白由载脂蛋白（apoAequorin）和（S）-2-过氧腔肠素（CTZ-OOH）组成，被认为是酶（apoAequorin）和底物（腔肠素和分子氧）在酶促反应中的瞬态复合物。在各种蛋白质变性条件下表征了水母发光蛋白中 CTZ-OOH 的降解过程。通过酸处理，CTZ-OOH的主要产物是腔肠胺（CTM），而不是腔肠酰胺（CTMD），并且没有观察到明显的发光。CTZ-OOH 的 CTM 对应物通过液相色谱/电喷雾电离-飞行时间质谱 (LC/ESI-TOF-MS) 鉴定为 4-羟基苯丙酮酸 (4HPPA) 和 4-羟基苯乙酸 (4HPAA)。在水母发光蛋白与 Ca 2+的发光反应中，检测到相似数量的 4HPPA 和 4HPAA，表明 CTM 是由 CTZ-OOH 通过二氧杂环丁酮阴离子的两条途径形成的，而不是通过 CTMD 的水解形成的。
• Selective protein modification by the hydroperoxide intermediate in a photoprotein, aequorin
  作者：Issei Doi、Masaki Kuse、Toshio Nishikawa、Minoru Isobe

  DOI：10.1016/j.bmc.2009.03.033

  日期：2009.5

  During the course of protein modi. cation program, we employed a recombinant aequorin, the apo-protein reconstituted with coelenterazine, and found out that the photolytic hyperperoxide modified three S-SCH2CHOHCHOHCH2SH groups to -S-SCH2CHOHCH = CH-S = O) H or -S-SCH2CHOHCH = CH-S(= O)OH of terminal DTT connected to cysteine residues of the C-145, C-152 and C-180, which turned out to locate near the chromophore. (C) 2009 Elsevier Ltd. All rights reserved.