S-4-methylbenzoyl coenzyme A | 149834-12-8

• 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: S-4-methylbenzoyl coenzyme A
• 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] 4-methylbenzenecarbothioate
• CAS: 149834-12-8
• 化学式: C₂₉H₄₂N₇O₁₇P₃S
• 分子量: 885.676
• InChiKey: UVPLYHXZJGQOQS-SXQYHYLKSA-N

物化性质

• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  57
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  389
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  S-4-methylbenzoyl coenzyme A 在 titanium(III) citrate 、 methyl-BzCoA reductase Tcl 作用下， 以 aq. buffer 为溶剂， 生成 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] 4-methylcyclohexa-1,5-diene-1-carbothioate
  参考文献：
  名称：

  一种催化多功能的苯甲酰基-CoA还原酶，是反硝化细菌中甲基和卤代苯甲酸酯降解的关键酶。

  摘要：

  I类苯甲酰辅酶A（BzCoA）还原酶（BCR）是芳香族化合物厌氧降解的关键酶。他们可能通过基于自由基的，类似桦木的还原机制催化中央BzCoA中间体及其类似物向ATP依赖性还原成共轭环状1,5-二烯酰基-CoA。于1995年发现的反硝化细菌芳香龙虾（BCRTar）的酶至今仍是唯一分离出的且可从生物化学途径获得的BCR，主要是因为BCR极不稳定，并且迄今为止其异源生产已大大失败。这里，我们描述了一个平台，用于从大肠杆菌中的相关反硝化物种Thauera chlorobenzoica（MBRTcl）编码指定的3-甲基苯甲酰辅酶A还原酶的四个结构基因的异源表达。有人建议参与降解甲基取代的BzCoA类似物。重组的MBRTcl具有一个αβγδ亚基结构，包含三个低电势[4Fe-4S]簇，并且高度不稳定。它催化了BzCoA的ATP依赖性还原脱芳香化反应，每转移两个电子就水解2.3-2.8个ATP，并优先在间

  DOI：

  10.1074/jbc.ra118.003329
• 作为产物：
  描述：

  4-甲基苯甲酰基碳酸乙酯 、 coenzyme A disodium salt 在 碳酸氢钠 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.5h， 生成 S-4-methylbenzoyl coenzyme A
  参考文献：
  名称：

  Point Mutations (Q19P and N23K) Increase the Operational Solubility of a 2α-O-Benzoyltransferase that Conveys Various Acyl Groups from CoA to a Taxane Acceptor

  摘要：

  Two site-directed Mutations within the wild-type 2-O-benzoyltransferase (tbt) cDNA, from Taxus cuspidata plants, yielded air encoded protein containing replacement amino acids at Q19P and N23K that trial) to a solvent-exposed loop region. The likely significant changes in the biophysical properties invoked by these mutations Caused the overexpressed, modified TBT (mTBT) to partition into the Soluble enzyme fraction about 5-fold greater than the wild-type enzyme. Sufficient protein could now be acquired to examine the scope of the substrate specificity of mTBT by incubation with 7,13-O,O-diacetyl-2-O-debenzoylbaceatin III that was mixed individually with various substituted benzoyls, alkanoyls, and (E)-butenoyl CoA donors. The mTBT catalyzed the conversion of each 7,13-O,O-diacetyl-2-O-debenzoylbaccatin III to several 7,13-O,O-diacetyl-2-O-acyl-2-O-debenzoylbaccatin III analogues. The relative catalytic efficiency of mTBT with the 7,13-O,O-diacetyl-2-O-debenzoyl surrogate Substrate and heterole carbonyl CoA substrates was slightly greater than with the natural aroyl substrate benzoyl CoA, While substituted benzoyl CoA thioesters were less productive. Short-chain hydrocarbon carbonyl and cyclohexanoyl CoA thioesters were also productive, where C-4 Substrates were transferred by mTBT with similar to 10- to 17-fold greater catalytic efficiency compared to the transfer of benzoyl. The described broad specificity of mTBT suggests (flat a plethora of 2-O-acyl variants of the antimitotic paclitaxel can be assembled through biocatalytic sequences.

  DOI：

  10.1021/np900524d

文献信息

• Structure–activity analysis of base and enzyme-catalyzed 4-hydroxybenzoyl coenzyme A hydrolysis
  作者：Feng Song、Zhihao Zhuang、Debra Dunaway-Mariano

  DOI：10.1016/j.bioorg.2006.07.002

  日期：2007.2

  a slope (rho) of 1.5. In the case of the enzyme-catalyzed hydrolysis, the kcat/Km values measured for the para-substituted analogs defined substrate specificity. Asp32 was shown to play a key role in substrate recognition, and in particular, in the discrimination between the targeted substrate and other cellular benzoyl-CoA thioesters.

  在这项研究中，碱催化水解的二级速率常数k2和野生型假单胞菌sp的kcat，Km和kcat / Km值。测量了CBS3 4-羟基苯甲酰基辅酶A（4-HBA-CoA）硫酯酶催化的4-HBA-CoA及其对位取代类似物的水解。对于碱催化的水解，logk2对对位取代基的sigma值的图是线性的，斜率（rho）为1.5。在酶催化水解的情况下，对位取代的类似物测得的kcat / Km值定义了底物特异性。Asp32已显示在底物识别中，特别是在目标底物与其他细胞性苯甲酰基-CoA硫酯的区分中起关键作用。
• MICROORGANISMS AND METHODS FOR THE BIOSYNTHESIS OF AROMATICS, 2,4-PENTADIENOATE AND 1,3-BUTADIENE
  申请人：Osterhout Robin E.

  公开号：US20120021478A1

  公开（公告）日：2012-01-26

  The invention provides non-naturally occurring microbial organisms having a toluene, benzene, p-toluate, terephthalate, (2-hydroxy-3-methyl-4-oxobutoxy)phosphonate, (2-hydroxy-4-oxobutoxy)phosphonate, benzoate, styrene, 2,4-pentadienoate, 3-butene-1ol or 1,3-butadiene pathway. The invention additionally provides methods of using such organisms to produce toluene, benzene, p-toluate, terephthalate, (2-hydroxy-3-methyl-4-oxobutoxy)phosphonate, (2-hydroxy-4-oxobutoxy)phosphonate, benzoate, styrene, 2,4-pentadienoate, 3-butene-1ol or 1,3-butadiene.

  本发明提供了一种非自然出现的微生物有甲苯、苯、对甲苯酸、对苯二甲酸、(2-羟基-3-甲基-4-氧代丁氧基)膦酸酯、(2-羟基-4-氧代丁氧基)膦酸酯、苯甲酸、苯乙烯、2,4-戊二烯酸、3-丁烯-1-醇或1,3-丁二烯代谢途径。此外，本发明还提供了使用这些微生物制备甲苯、苯、对甲苯酸、对苯二甲酸、(2-羟基-3-甲基-4-氧代丁氧基)膦酸酯、(2-羟基-4-氧代丁氧基)膦酸酯、苯甲酸、苯乙烯、2,4-戊二烯酸、3-丁烯-1-醇或1,3-丁二烯的方法。
• Thioester-mediated biocatalytic amide bond synthesis with in situ thiol recycling
  作者：Christian Schnepel、Laura Rodríguez Pérez、Yuqi Yu、Antonio Angelastro、Rachel S. Heath、Max Lubberink、Francesco Falcioni、Keith Mulholland、Martin A. Hayes、Nicholas J. Turner、Sabine L. Flitsch

  DOI：10.1038/s41929-022-00889-x

  日期：——

  catalyses the conversion of a wide range of carboxylic acids to acyl-S-Coenzyme A and other thioesters in good yields. CARsr-A was used in situ as part of a recycling system to regenerate thioesters for acyl-S-Coenzyme A-dependent enzymes in one-pot reactions. This concept of thioester recycling is demonstrated with a range of acyltransferases that allow the formation of diverse amides and the non-native

  羧酸活化为硫酯在生物学中起着重要作用。然而，生化研究和生物技术应用受到普遍缺乏硫酯的阻碍，尤其是那些基于辅酶 A (CoA-SH) 的硫酯。在这里，我们通过利用羧酸还原酶 (CAR sr ) 的混杂活性展示了一种通用的硫酯回收酶。CAR sr (CAR sr -A)的腺苷酸化结构域催化各种羧酸以良好的产率转化为酰基-S-辅酶 A 和其他硫酯。汽车_-A 原位用作回收系统的一部分，以在一锅反应中为酰基-S-辅酶 A 依赖性酶再生硫酯。这种硫酯循环的概念通过一系列酰基转移酶得到证明，这些酰基转移酶允许使用表观遗传作者赖氨酸乙酰转移酶 HATp300 形成不同的酰胺和组蛋白衍生肽中赖氨酸侧链的非天然酰化。总的来说，这些结果为硫酯形成向酰胺形成及以后的形成建立了一个通用平台。
• Microorganisms and methods for the biosynthesis of aromatics, 2,4-pentadienoate and 1,3-butadiene
  申请人：Genomatica, Inc.

  公开号：EP2607340A1

  公开（公告）日：2013-06-26

  The invention provides non-naturally occurring microbial organisms having a 1,3-butadiene pathway. The invention additionally provides methods of using such organisms to produce 1,3-butadiene.

  本发明提供了具有 1,3-丁二烯途径的非天然微生物。此外，本发明还提供了利用此类生物生产 1,3-丁二烯的方法。
• MICROORGANISMS AND METHODS FOR THE PRODUCTION OF 1.4- CYCLOHEXANEDIMETHANOL
  申请人：Genomatica, Inc.

  公开号：EP2652141A1

  公开（公告）日：2013-10-23