(3E)-1-methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-2H-ψ,ψ-caroten-2-ol | 13836-67-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3E)-1-methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-2H-ψ,ψ-caroten-2-ol
• 英文别名: (+/-)-1-methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-ψ,ψ-caroten-2-ol；(+/-)-2-Methoxy-2,6,10,14,19,23,27,31-octamethyl-dotriaconta-4t,6t,8t,10t,12t,14t,16t,18t,20t,22t,26t,30-dodecaen-3-ol；(+/-)-1-Methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-ψ,ψ-carotin-2-ol；Spheroidenol；(+/-)-spheroidenol；2-Hydroxyspheroidene；(4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,26E)-2-methoxy-2,6,10,14,19,23,27,31-octamethyldotriaconta-4,6,8,10,12,14,16,18,20,22,26,30-dodecaen-3-ol
• CAS: 13836-67-4
• 化学式: C₄₁H₆₀O₂
• 分子量: 584.926
• InChiKey: IYSJCVOSCTVRGJ-FZFXUSNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3E)-1-methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-2H-ψ,ψ-caroten-2-ol 、 氢(+1)阳离子 、 氧气 、 [2Fe-2S]¹⁺ 生成 2,2-Dihydroxyspheroidene 、 水 、 [2Fe-2S]²⁺
  参考文献：
  名称：

  在大肠杆菌中表达的球状红杆菌球状烯单加氧酶 CrtA 的新活性。

  摘要：

  球形红细菌的球状烯单加氧酶 CrtA 在大肠杆菌的非天然底物末端引入酮基和/或羟基，从而产生新型氧代胡萝卜素。含血红素的CrtA 不是P450 酶，而是一种新型的加氧酶。

  DOI：

  10.1128/aem.01606-10
• 作为产物：
  描述：

  2,7-二甲基-2,4,6-辛三烯二醛 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 Petroleum ether 、 苯 为溶剂， 生成 (3E)-1-methoxy-3,4-didehydro-1,2,7',8'-tetrahydro-2H-ψ,ψ-caroten-2-ol
  参考文献：
  名称：

  类胡萝卜素和相关化合物。第十六部分。螺旋黄嘌呤，氯黄嘌呤，椭球体和椭球烯酮的结构和合成研究

  摘要：

  通过降解和核磁共振谱研究清楚地确定了螺菌黄质（视紫红霉素）的结构。相似的研究表明，氯黄嘌呤，椭球体（“ Y颜料”）和椭球酮（“ R颜料”）的结构；这些结构已通过总合成得到证实。

  DOI：

  10.1039/j39660002166

文献信息

• Goodwin et al., Biochemical Journal, 1956, vol. 64, p. 486,490
  作者：Goodwin et al.

  DOI：——

  日期：——
• Catalytic properties of the expressed acyclic carotenoid 2-ketolases from Rhodobacter capsulatus and Rubrivivax gelatinosus
  作者：Tanja Gerjets、Sabine Steiger、Gerhard Sandmann

  DOI：10.1016/j.bbalip.2008.12.006

  日期：2009.2

  Purple photosynthetic bacteria synthesize the acyclic carotenoids spheroidene and spirilloxanthin which are ketolated to spheroidenone and 2,2'-diketospirilloxanthin under aerobic growth. For the studies of the catalytic reaction of the ketolating enzyme, the crtA genes from Rubrivivax gelatinosus and Rhodobacter capsulatus encoding acyclic carotenoid 2-ketolases were expressed in Escherichia coli to functional enzymes. With the purified enzyme from the latter, the requirement of molecular oxygen and reduced ferredoxin for the catalytic activity was determined. Furthermore, the putative intermediate 2-HO-spheroidene was in vitro converted to the corresponding 2-keto product. Therefore, a monooxygenase mechanism involving two consecutive hydroxylation steps at C-2 were proposed for this enzyme. By functional pathway complementation studies in E coli and enzyme kinetic studies, the product specificity of both enzymes were investigated. it appears that the ketolases could catalyze most intermediates and products of the spheroidene and spirilloxanthin pathway. This was also the case for the enzyme from Rba. capsulatus from which spirilloxanthin synthesis is absent. In general, the ketolase of Rvi. gelatinosus had a better specificity for spheroidene, HO-spheroidene and spirilloxanthin as substrates than the ketolase from Rba. capsulatus. (C) 2008 Elsevier B.V. All rights reserved.
• Carotenoids and related compounds. Part XVI. Structural and synthetic studies on spirilloxanthin, chloroxanthin, spheroidene, and spheroidenone
  作者：M. S. Barber、L. M. Jackman、P. S. Manchand、B. C. L. Weedon

  DOI：10.1039/j39660002166

  日期：——

  The structure of spirilloxanthin (rhodoviolascin) was unambiguously determined by degradative and nuclear magnetic resonance spectral studies. Similar studies indicated the structures of chloroxanthin, spheroidene (“Pigment Y”), and spheroidenone (“Pigment R”); these structures have been confirmed by total syntheses.

  通过降解和核磁共振谱研究清楚地确定了螺菌黄质（视紫红霉素）的结构。相似的研究表明，氯黄嘌呤，椭球体（“ Y颜料”）和椭球酮（“ R颜料”）的结构；这些结构已通过总合成得到证实。
• Novel Activity of <i>Rhodobacter sphaeroides</i> Spheroidene Monooxygenase CrtA Expressed in <i>Escherichia coli</i>
  作者：Pyung Cheon Lee、Erik Holtzapple、Claudia Schmidt-Dannert

  DOI：10.1128/aem.01606-10

  日期：2010.11

  sphaeroides introduces a keto group and/or hydroxy group at the ends of nonnative substrates in Escherichia coli, resulting in the production of novel oxocarotenoids. The heme-containing CrtA is not a P450 enzyme but a new type of oxygenase.

  球形红细菌的球状烯单加氧酶 CrtA 在大肠杆菌的非天然底物末端引入酮基和/或羟基，从而产生新型氧代胡萝卜素。含血红素的CrtA 不是P450 酶，而是一种新型的加氧酶。