2,2-Dihydroxyspheroidene

• 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: 2,2-Dihydroxyspheroidene
• 英文别名: (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-dodecaene-3,3-diol
• 化学式: C₄₁H₆₀O₃
• 分子量: 600.9
• InChiKey: YCYFTLOJTFQQOD-FZFXUSNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  44
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-Dihydroxyspheroidene 生成 水 、 spheroidenone
  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：

  (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

文献信息

• 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.
• 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。