benzoyl-CoA(4-)

• 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: benzoyl-CoA(4-)
• 英文别名: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[(3R)-4-[[3-(2-benzoylsulfanylethylamino)-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] phosphate
• 化学式: C28H36N7O17P3S-4
• 分子量: 867.6
• InChiKey: VEVJTUNLALKRNO-TYHXJLICSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  56
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  400
• 氢给体数：
  5
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  O2CC6H4NH2-o(1-) 、 benzoyl-CoA(4-) 生成 coenzyme A 、 N-Benzoylanthranilate
  参考文献：
  名称：

  香石竹细胞培养物中植物抗毒素的生物合成：诱导苯甲酰辅酶A：邻氨基苯甲酸N-苯甲酰转移酶活性。

  摘要：

  已经显示石竹石竹的细胞培养物积累了N-苯甲酰基-4-甲氧基邻氨基苯甲酸，先前被鉴定为植物抗毒素甲氧基二氨基乙酰胺B，响应于用从巨大疫霉菌的细胞壁分离的粗激发子的处理。 .sp。甘氨酸或商业酵母提取物。在苯甲酰辅酶A存在下，来自诱导细胞的无细胞提取物可有效催化邻氨基苯甲酸的N-苯甲酰化。已显示部分纯化的转移酶对邻氨基苯甲酸具有特异性，几乎没有对4-羟基邻氨基苯甲酸的活性，而除苯甲酰基-CoA以外的酰基供体，例如水杨酰基-，肉桂酰基-或4-香豆酰基-CoA也被接受。细胞的诱导剂处理另外诱导了S-腺苷-L-蛋氨酸：N-苯甲酰基-4-羟基邻氨基苯甲酸4-O-甲基转移酶活性。因此，我们建议甲氧基二乙酰胺B通过N-苯甲酰基-4-羟基邻氨基苯甲酸衍生自N-苯并基邻氨基苯甲酸。深色生长的细胞几乎没有N-苯甲酰转移酶活性（约8 mu kat / kg），在加入引发剂后6 h内其活性增加了约9倍。另外，在这些条件下，细胞的苯丙氨酸氨解酶活性在约5

  DOI：

  10.1016/0003-9861(89)90376-7
• 作为产物：
  描述：

  氢(+1)阳离子 、 isophthalyl-CoA 生成 benzoyl-CoA(4-) 、 二氧化碳
  参考文献：
  名称：

  Anaerobic degradation of xenobiotic isophthalate by the fermenting bacterium Syntrophorhabdus aromaticivorans

  摘要：

  海洋硫酸盐还原菌、芳香族化合物降解脱氮菌等。

  DOI：

  10.1038/s41396-019-0348-5

文献信息

• Enzymatic Characterization and Elucidation of the Catalytic Mechanism of a Recombinant Bovine Glycine<i>N</i>-Acyltransferase
  作者：Christoffel P. S. Badenhorst、Maritza Jooste、Alberdina A. van Dijk

  DOI：10.1124/dmd.111.041657

  日期：2012.2

  Glycine conjugation, a phase II detoxification process, is catalyzed by glycine N -acyltransferase (GLYAT; E.C. 2.3.1.13). GLYAT detoxifies various xenobiotics, such as benzoic acid, and endogenous organic acids, such as isovaleric acid, which makes GLYAT important in the management of organic acidemias in humans. We cloned the open reading frame encoding the bovine ortholog of GLYAT from bovine liver mRNA into the bacterial expression vector pColdIII. The recombinant enzyme was expressed, partially purified, and enzymatically characterized. Protein modeling was used to predict Glu226 of bovine GLYAT to be catalytically important. This was assessed by constructing an E226Q mutant and comparing its enzyme kinetics to that of the wild-type recombinant bovine GLYAT. The Michaelis constants for benzoyl-CoA and glycine were determined and were similar for wild-type recombinant GLYAT, E226Q recombinant GLYAT, and GLYAT present in bovine liver. At pH 8.0, the E226Q mutant GLYAT had decreased activity, which could be compensated for by increasing the reaction pH. This suggested a catalytic mechanism in which Glu226 functions to deprotonate glycine, facilitating nucleophilic attack on the acyl-CoA. The recombinant bovine GLYAT enzyme, combined with this new understanding of its active site and reaction mechanism, could be a powerful tool to investigate the functional significance of GLYAT sequence variations. Eventually, this should facilitate investigations into the impact of known and novel sequence variations in the human GLYAT gene.

  甘氨酸缀合是 II 期解毒过程，由甘氨酸 N-酰基转移酶 (GLYAT；E.C. 2.3.1.13) 催化。 GLYAT 可以解毒各种外源性物质（例如苯甲酸）和内源性有机酸（例如异戊酸），这使得 GLYAT 在人类有机酸血症的治疗中发挥着重要作用。我们将牛肝脏 mRNA 中编码 GLYAT 的牛直系同源物的开放阅读框克隆到细菌表达载体 pColdIII 中。表达、部分纯化重组酶并进行酶学表征。使用蛋白质模型来预测牛 GLYAT 的 Glu226 具有重要的催化作用。这是通过构建 E226Q 突变体并将其酶动力学与野生型重组牛 GLYAT 的酶动力学进行比较来评估的。测定了苯甲酰辅酶A和甘氨酸的米氏常数，并且与野生型重组GLYAT、E226Q重组GLYAT和牛肝脏中存在的GLYAT相似。在 pH 8.0 时，E226Q 突变体 GLYAT 的活性降低，这可以通过提高反应 pH 值来补偿。这表明 Glu226 具有使甘氨酸去质子化的催化机制，促进对酰基辅酶 A 的亲核攻击。重组牛 GLYAT 酶，结合对其活性位点和反应机制的新认识，可能成为研究 GLYAT 序列变异功能意义的有力工具。最终，这将有助于研究人类 GLYAT 基因中已知和新的序列变异的影响。
• Coenzyme A-dependent Aerobic Metabolism of Benzoate via Epoxide Formation
  作者：Liv J. Rather、Bettina Knapp、Wolfgang Haehnel、Georg Fuchs

  DOI：10.1074/jbc.m110.124156

  日期：2010.7

  (protocatechuate, mainly in fungi). We have shown before that many bacteria, e.g. Azoarcus evansii, the organism studied here, use a completely different mechanism. This elaborate pathway requires formation of benzoyl-CoA, followed by an oxygenase reaction and a nonoxygenolytic ring cleavage. Benzoyl-CoA transformation is catalyzed by the iron-containing benzoyl-CoA oxygenase (BoxB) in conjunction with

  在芳香底物的有氧代谢中，加氧酶利用分子氧羟基化并最终裂解芳香环。在常见的中间体苯甲酸酯的情况下，开环底物是儿茶酚（在细菌中）或 3,4-二羟基苯甲酸酯（原儿茶酸酯，主要在真菌中）。我们之前已经证明，许多细菌，例如这里研究的有机体 Azoarcus evansii，使用完全不同的机制。这种复杂的途径需要形成苯甲酰辅酶 A，然后是加氧酶反应和非氧化环裂解。苯甲酰-CoA 转化由含铁的苯甲酰-CoA 加氧酶 (BoxB) 与 FAD 和含有还原酶 (BoxA) 的铁硫中心共同催化，后者从 NADPH 中提供电子。在这里我们表明苯甲酰辅酶 A 加氧酶实际上不形成 2, 苯甲酰-CoA 的 3-二氢二醇，如以前所假设的，但 2,3-环氧化物。烯酰-CoA 水合酶 (BoxC) 使用两个分子的水首先水解打开 2,3-环氧苯甲酰-CoA 的环，这可以通过其互变异构的七元氧塞平环形式进行。然后将环 C2 水解为甲酸，产生
• Characterization of seed‐specific benzoyloxyglucosinolate mutations in <i>Arabidopsis thaliana</i>
  作者：Daniel J. Kliebenstein、John C. D’Auria、Aditi S. Behere、Jae Hak Kim、Kevin L. Gunderson、John N. Breen、Grace Lee、Jonathan Gershenzon、Robert L. Last、Georg Jander

  DOI：10.1111/j.1365-313x.2007.03205.x

  日期：2007.9

  Glucosinolates are secondary metabolites involved in pathogen and insect defense of cruciferous plants. Although seeds and vegetative tissue often have very different glucosinolate profiles, few genetic factors that determine seed glucosinolate accumulation have been identified. An HPLC‐based screen of 5500 mutagenized Arabidopsis thaliana lines produced 33 glucosinolate mutants, of which 21 have seed‐specific changes. Five of these mutant lines, representing three genetic loci, are compromised in the biosynthesis of benzoyloxyglucosinolates, which are only found in seeds and young seedlings of A. thaliana. Genetic mapping and analysis of T‐DNA insertions in candidate genes identified BZO1 (At1g65880), which encodes an enzyme with benzoyl‐CoA ligase activity, as being required for the accumulation of benzoyloxyglucosinolates. Long‐chain aliphatic glucosinolates are elevated in bzo1 mutants, suggesting substrate competition for the common short‐chain aliphatic glucosinolate precursors. Whereas bzo1 mutations have seed‐specific effects on benzoyloxyglucosinolate accumulation, the relative abundance of 3‐benzoyloxypropyl‐ and 4‐benzoyloxybutylglucosinolates depends on the maternal genotype.

  摘要葡萄糖苷酸盐是十字花科植物防御病原体和昆虫的次级代谢产物。虽然种子和植株组织通常具有非常不同的葡萄糖苷酸特征，但决定种子葡萄糖苷酸积累的遗传因素却很少被发现。对 5500 个诱变拟南芥品系进行的基于 HPLC 的筛选产生了 33 个葡萄糖苷酸突变体，其中 21 个具有种子特异性变化。其中 5 个突变株代表 3 个遗传位点，它们在苯甲酰氧基葡萄糖苷酸盐的生物合成中受到影响，而这种物质只存在于拟南芥的种子和幼苗中。通过对候选基因的 T-DNA 插入进行遗传测绘和分析，发现 BZO1（At1g65880）是苯甲酰氧基葡萄糖苷酸积累所必需的，它编码一种具有苯甲酰-CoA 连接酶活性的酶。在 bzo1 突变体中，长链脂肪族葡萄糖苷酸含量升高，这表明底物竞争常见的短链脂肪族葡萄糖苷酸前体。bzo1 突变体对苯甲酰氧基葡萄糖苷酸积累具有种子特异性影响，而 3-苯甲酰氧基丙基葡萄糖苷酸和 4-苯甲酰氧基丁基葡萄糖苷酸的相对丰度则取决于母本基因型。
• 4-Hydroxybenzoate-coenzyme A ligase from Rhodopseudomonas palustris: purification, gene sequence, and role in anaerobic degradation
  作者：J Gibson、M Dispensa、G C Fogg、D T Evans、C S Harwood

  DOI：10.1128/jb.176.3.634-641.1994

  日期：1994.2

  Anaerobic metabolism of most aromatic acids is initiated by coenzyme A thioester formation. Rhodopseudomonas palustris grows well under anaerobic, phototrophic conditions with many aromatic acids, including benzoate and 4-hydroxybenzoate, as a carbon source. A coenzyme A ligase that reacts with 4-hydroxybenzoate was purified from 4-hydroxybenzoate-grown cells of R. palustris. This enzyme required MgATP, reduced coenzyme A, and 4-hydroxybenzoate, benzoate, or cyclohex-1,4-dienecarboxylate for optimal activity but also used phosphopantetheine, cyclohex-2,5-dienecarboxylate, and 4-fluorobenzoate at lower rates. The 4-hydroxybenzoate-coenzyme A ligase differed in molecular characteristics from a previously described benzoate-coenzyme A ligase from R. palustris, and the two ligases did not cross-react immunologically. The gene encoding the 4-hydroxybenzoate enzyme was cloned and sequenced. The deduced gene product showed about 20% amino acid identity with bacterial coenzyme A ligases involved in aerobic degradation of aromatic acids. An R. palustris mutant carrying a disrupted 4-hydroxybenzoate-coenzyme A ligase gene was unable to grow with 4-hydroxybenzoate under anaerobic conditions, indicating that the enzyme is essential for anaerobic degradation of this compound.

  大多数芳香族酸的厌氧代谢是通过辅酶A硫酯形成来启动的。沼泽紫杆菌在厌氧、光合条件下，利用苯甲酸和4-羟基苯甲酸等多种芳香族酸作为碳源生长良好。从R. palustris的4-羟基苯甲酸生长细胞中纯化出一种与4-羟基苯甲酸反应的辅酶A连接酶。该酶需要MgATP、还原辅酶A以及4-羟基苯甲酸、苯甲酸或环己-1,4-二烯羧酸以获得最佳活性，但也以较低速率利用磷酸泛酰乙醇胺、环己-2,5-二烯羧酸和4-氟苯甲酸。4-羟基苯甲酸-辅酶A连接酶在分子特性上与之前描述的来自R. palustris的苯甲酸-辅酶A连接酶不同，并且这两种连接酶在免疫学上没有交叉反应。克隆和测序了编码4-羟基苯甲酸酶的基因。推导的基因产物与参与芳香族酸的好氧降解的细菌辅酶A连接酶具有约20％的氨基酸同源性。携带破坏的4-羟基苯甲酸-辅酶A连接酶基因的R. palustris突变体无法在厌氧条件下利用4-羟基苯甲酸生长，表明该酶对于该化合物的厌氧降解是必需的。
• Characterization of the CoA ligases of human liver mitochondria catalyzing the activation of short- and medium-chain fatty acids and xenobiotic carboxylic acids
  作者：Donald A. Vessey、Michael Kelley、Robert S. Warren

  DOI：10.1016/s0304-4165(99)00088-4

  日期：1999.8

  Two distinct forms of xenobiotic/medium-chain fatty acid:CoA ligase (XM-ligase) were isolated from human liver mitochondria. They were referred to as HXM-A and HXM-B based on their order of elution from a DEAE-cellulose column. Activity of the two ligases was determined toward 15 different carboxylic acids. HXM-A represented 60-80% of the benzoate activity in the lysate, and kinetic analysis revealed

  从人肝线粒体中分离出两种不同形式的异源生物/中链脂肪酸：CoA连接酶（XM-连接酶）。根据它们从DEAE-纤维素柱上洗脱的顺序，它们被称为HXM-A和HXM-B。确定了两种连接酶对15种不同羧酸的活性。HXM-A代表裂解物中苯甲酸酯活性的60-80％，动力学分析表明苯甲酸酯是最好的底物（最高V（max）/ K（m））。该酶还具有中链脂肪酸：CoA连接酶活性。HXM-B具有最大的己酸活性，己酸是其最佳底物。然而，它也对许多异生羧酸具有活性。这两种人XM-连接酶与先前表征的牛XM-连接酶的比较表明它们在动力学上是不同的。当用苯甲酸作为底物进行分析时，HXM-A和HXM-B都绝对依赖Mg（2+）或Mn（2+）的活性。此外，添加一价阳离子（K（+），Rb（+）或NH（4）（+））刺激HXM-A活性增加> 30倍，HXM-B活性增加4倍。对于这两种形式，对直链脂肪酸的活性受K（+）的刺激均少于对苯甲