环己烷羧基-辅酶A | 5960-12-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 环己烷羧基-辅酶A
• 英文名称: cyclohexancarboxyl-CoA
• 英文别名: cyclohexane-1-carbonyl-CoA；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] cyclohexanecarbothioate
• CAS: 5960-12-3
• 化学式: C₂₈H₄₆N₇O₁₇P₃S
• 分子量: 877.697
• InChiKey: QRSKGVRHSLILFG-TYHXJLICSA-N

物化性质

• 溶解度：
  PBS（pH 7.2）：10 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  56
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  389
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  1-monoenoyl-CoA 在 3-吗啉丙磺酸 、 titanium(III) citrate 、 7,8-dihydro-2,12-dimethyl-6H-dipyrido[1,2-a:2',1'-c][1,4]diazepinediium dibromide 、 sodium chloride 、 potassium hydroxide 、 magnesium chloride 作用下， 反应 0.01h， 生成 环己烷羧基-辅酶A
  参考文献：
  名称：

  Reversible Biological Birch Reduction at an Extremely Low Redox Potential

  摘要：

  The Birch reduction of aromatic rings to cyclohexadiene compounds is widely used in chemical synthesis and requires solvated electrons, the most potent reductants known in organic chemistry. Benzoyl-coenzyme A (CoA) reductases (BCR) are key enzymes in the anaerobic bacterial degradation of aromatic compounds and catalyze an analogous reaction under physiological conditions. Class I BCRs are FeS enzymes and couple the reductive dearomatization of benzoyl-CoA to cyclohexa-1,5-diene-1-carboxyl-CoA (dienoyl-CoA) to a stoichiometric ATP hydrolysis. Here, we report on a tungsten-containing class II BCR from Geobacter metallireducens that catalyzed the fully reversible, ATP-independent dearomatization of benzoyl-CoA to dienoyl-CoA. BCR additionally catalyzed the disproportionation of dienoyl-CoA to benzoyl-CoA/monoenoyl-CoA and the four- and six-electron reduction of benzoyl-CoA in the presence of a reduced low-potential bridged 2,2'-bipyridyl redox dye. Reversible redox titration experiments in the presence of this redox dye revealed a midpoint potential of E-0'= -622 mV for the benzoyl-CoA/dienoyl-CoA couple, which is far below the values of other known reversible substrate/product redox couples in enzymology. This work demonstrates the efficiency of reversible metalloenzyme catalysis, which in chemical synthesis can only be achieved under essentially irreversible conditions.

  DOI：

  10.1021/ja103448u

文献信息

• METHODS AND COMPOSITIONS FOR PRODUCING HYDROCARBONS
  申请人：SCHIRMER ANDREAS

  公开号：US20100221798A1

  公开（公告）日：2010-09-02

  Compositions and methods for producing hydrocarbons such as aldehydes, alkanes, and alkenes are described herein. Certain hydrocarbons can be used in biofuels.

  本文描述了用于生产醛、烷烃和烯烃等烃类化合物的组合物和方法。某些烃类化合物可以用于生物燃料。
• METHODS AND COMPOSITIONS RELATED TO THIOESTERASE ENZYMES
  申请人：Hom Louis

  公开号：US20100154293A1

  公开（公告）日：2010-06-24

  The present invention relates to novel mutant thioesterase enzymes and naturally-occurring equivalents thereof, compositions made from such enzymes and uses of thioesterase enzymes. In particular, the present invention provides mutant thioesterase enzymes that have altered properties, for example, altered substrate specificity, altered activity, altered selectivity, and/or altered proportional yields in the product mixtures. The present invention also provides polynucleotides encoding such mutant thioesterase enzymes, and vectors and host cells comprising such polynucleotides. The invention further provides for novel uses of thioesterases in the production of various fatty acid derivatives, which are useful as, or as components of, industrial chemicals and fuels.

  本发明涉及新型突变硫酯酶酶和自然存在的等效物，由这些酶制成的组合物以及硫酯酶酶的用途。特别是，本发明提供具有改变性质的突变硫酯酶酶，例如改变底物特异性、改变活性、改变选择性和/或改变产物混合物中的比例收率。本发明还提供编码这种突变硫酯酶酶的多核苷酸，以及包含这种多核苷酸的载体和宿主细胞。本发明还提供了硫酯酶在生产各种脂肪酸衍生物中的新用途，这些衍生物可用作工业化学品和燃料的组成部分或作为工业化学品和燃料。
• A Pair of Atypical KAS III Homologues with Initiation and Elongation Functions Program the Polyketide Biosynthesis in Asukamycin
  作者：Xiaoli Yan、Jun Zhang、Hongqun Tan、Zhihao Liu、Kai Jiang、Wenya Tian、Mengmeng Zheng、Zhi Lin、Zixin Deng、Xudong Qu

  DOI：10.1002/anie.202200879

  日期：2022.5.2

  KAS IIIs are known to be involved in the initiation step of polyketide and fatty acid biosynthesis. In vitro reconstitution of the upper triene chain of asukamycin unveils two highly unusual KAS IIIs which both exhibit initiation and iterative elongation activity. Together with the permissive ketoreductase and dehydratase, these C−C bond-forming enzymes can synthesize a large variety of polyenes.

  已知 KAS III 参与聚酮化合物和脂肪酸生物合成的起始步骤。Asukamycin 上三烯链的体外重组揭示了两种非常不寻常的 KAS III，它们都表现出起始和迭代延伸活性。与允许的酮还原酶和脱水酶一起，这些 C-C 键形成酶可以合成多种多烯。
• An Atypical Acyl‐CoA Synthetase Enables Efficient Biosynthesis of Extender Units for Engineering a Polyketide Carbon Scaffold
  作者：Mengmeng Zheng、Jun Zhang、Wan Zhang、Lu Yang、Xiaoli Yan、Wenya Tian、Zhihao Liu、Zhi Lin、Zixin Deng、Xudong Qu

  DOI：10.1002/anie.202208734

  日期：2022.10.24

  new acyl-CoA synthetase (ACS, UkaQ) with broad substrate specificity and an unusual catalytic mode was identified. Its stability and catalytic activity were remarkably improved by protein engineering, enabling it to synthesize a large variety of acyl-CoAs. In combination with permissive carboxylases, diverse extender units were synthesized and used to engineer the polyketide carbon scaffold of antimycin

  鉴定了一种具有广泛底物特异性和不寻常催化模式的新型酰基辅酶 A 合成酶（ACS，UkaQ）。蛋白质工程显着提高了其稳定性和催化活性，使其能够合成多种酰基辅酶 A。结合允许的羧化酶，合成了多种扩展单元，并用于设计抗霉素的聚酮化合物碳支架。
• Cell-free synthesis of polyketides
  申请人：THE LELAND STANFORD JUNIOR UNIVERSITY

  公开号：EP1493814A1

  公开（公告）日：2005-01-05

  Cell-free systems which effect the production of polyketides employing modular polyketides synthases are described. Libraries of new and/or known polyketides may also be produced in cell-free systems employing aromatic PKS, modular PKS or both.

  本文描述了利用模块化多酮合成酶生产多酮的无细胞系统。新的和/或已知的多酮类化合物库也可在采用芳香族 PKS、模块化 PKS 或两者的无细胞系统中生产。