6-hydroxycyclohex-1-ene-1-carbonyl-CoA | 148471-95-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-hydroxycyclohex-1-ene-1-carbonyl-CoA
• 英文别名: S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 6-hydroxycyclohexene-1-carbothioate
• CAS: 148471-95-8
• 化学式: C₂₈H₄₄N₇O₁₈P₃S
• 分子量: 891.681
• InChiKey: WBCJUEJWJADAGR-CRVKRRNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  57
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  409
• 氢给体数：
  10
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  [(2R,3R,4R,5R)-5-(6-氨基嘌呤-9-基)-2-[[[[3-[2-(2-苯甲酰硫乙基氨基甲酰)乙基氨基甲酰]-3-羟基-2,2-二甲基-丙氧基]-羟基-磷酰]氧基-羟基-磷酰]氧基甲基]-4-羟基-四氢呋喃-3-基]氧基膦酸 在 titanium(III) citrate 、 benzoyl-coenzyme A reductase 、 cyclohexa-1,5-diene-1-carboxyl-CoA hydratase 、 水 作用下， 生成 1,5-dienoyl-CoA 、 6-hydroxycyclohex-1-ene-1-carbonyl-CoA
  参考文献：
  名称：

  Mechanism of Enzymatic Birch Reduction: Stereochemical Course and Exchange Reactions of Benzoyl-CoA Reductase

  摘要：

  Dearomatizing benzoyl-coenzyme A reductases (BCR) from facultatively anaerobic bacteria are key enzymes in the anaerobic degradation of aromatic compounds. They catalyze the ATP-dependent reduction of benzoyl-CoA (BCoA) to cyclohexa-1,5-diene-1-carboxyl-CoA (dienoyl-CoA). A Birch reduction mechanism involving alternate electron transfer and protonation steps has been proposed for BCR. In this work we reacted BCoA in H2O and D2O, and d(5)-BCoA in H2O with BCR and the second enzyme of the pathway, dienoyl-CoA hydratase (DCH). The 1,4 hydration product formed from the dienoyl-CoA, 6-hydroxycyclohex-1-ene-1-carbonyl-CoA, was analyzed by several NMR techniques. The results obtained indicate that BCR stereoselectively forms the trans-dienoyl-CoA product, and DCH stereoselectively catalyzes a trans-1,4 water addition. Moreover, unexpected proton exchanges at C-2 and C-6 were observed. They indicate that a free

  DOI：

  10.1021/ja805091w

文献信息

• ANALYSIS AND ENHANCEMENT OF METABOLIC PATHWAYS FOR METHANOGENESIS
  申请人：Havemen Shelley

  公开号：US20100035309A1

  公开（公告）日：2010-02-11

  Processes for biogenic production of a hydrogen-carbon-containing fluid from a hydrocarbon containing formation are described. The processes may include providing in the formation an anaerobic microorganism consortium containing one or more enzymes to activate a starting hydrocarbon by an addition of a chemical group to the hydrocarbon. The processes may further include converting the activated hydrocarbon into the hydrogen-carbon-containing fluid through one or more intermediate hydrocarbons, and recovering the hydrogen-carbon-containing fluid from the formation.
• Mechanism of Enzymatic Birch Reduction: Stereochemical Course and Exchange Reactions of Benzoyl-CoA Reductase
  作者：Bärbel Thiele、Oliver Rieder、Bernard T. Golding、Michael Müller、Matthias Boll

  DOI：10.1021/ja805091w

  日期：2008.10.29

  Dearomatizing benzoyl-coenzyme A reductases (BCR) from facultatively anaerobic bacteria are key enzymes in the anaerobic degradation of aromatic compounds. They catalyze the ATP-dependent reduction of benzoyl-CoA (BCoA) to cyclohexa-1,5-diene-1-carboxyl-CoA (dienoyl-CoA). A Birch reduction mechanism involving alternate electron transfer and protonation steps has been proposed for BCR. In this work we reacted BCoA in H2O and D2O, and d(5)-BCoA in H2O with BCR and the second enzyme of the pathway, dienoyl-CoA hydratase (DCH). The 1,4 hydration product formed from the dienoyl-CoA, 6-hydroxycyclohex-1-ene-1-carbonyl-CoA, was analyzed by several NMR techniques. The results obtained indicate that BCR stereoselectively forms the trans-dienoyl-CoA product, and DCH stereoselectively catalyzes a trans-1,4 water addition. Moreover, unexpected proton exchanges at C-2 and C-6 were observed. They indicate that a free