feruloyl CoA

• 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: feruloyl 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] 3-(4-hydroxy-3-methoxyphenyl)prop-2-enethioate
• 化学式: C₃₁H₄₄N₇O₁₉P₃S
• 分子量: 943.713
• InChiKey: GBXZVJQQDAJGSO-HSJNEKGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  61
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  418
• 氢给体数：
  10
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  feruloyl CoA 在 caffeoyl-CoA O-methyltransferase 、 cinnamyl alcohol dehydrogenase 作用下， 生成 松柏醇
  参考文献：
  名称：

  Physicochemical properties, antioxidant activities and comprehensive phenolic profiles of tea-macerated Chardonnay wine and model wine

  摘要：

  DOI：

  10.1016/j.foodchem.2023.137748
• 作为产物：
  描述：

  咖啡酸 在 hydroxycinnamic acids/hydroxycinnamoyl CoA esters O-methyltransferase 、 4-coumarate-CoA ligase 作用下， 生成 feruloyl CoA
  参考文献：
  名称：

  Physicochemical properties, antioxidant activities and comprehensive phenolic profiles of tea-macerated Chardonnay wine and model wine

  摘要：

  DOI：

  10.1016/j.foodchem.2023.137748

文献信息

• Functional Characterization of a Hydroxyacid/Alcohol Hydroxycinnamoyl Transferase Produced by the Liverwort Marchantia emarginata
  作者：Ping-Ping Wang、Hui Liu、Shuai Gao、Ai-Xia Cheng

  DOI：10.3390/molecules22111854

  日期：——

  The aerial organs of most terrestrial plants are covered by a hydrophobic protective cuticle. The main constituent of the cuticle is the lipid polyester cutin, which is composed of aliphatic and aromatic domains. The aliphatic component is a polyester between fatty acid/alcohol and hydroxycinnamoyl acid. The BAHD/HxxxD family enzymes are central to the synthesis of these polyesters. The nature of this class of enzymes in bryophytes has not been explored to date. Here, a gene encoding a fatty ω-hydroxyacid/fatty alcohol hydroxycinnamoyl transferase (HFT) has been isolated from the liverwort Marchantia emarginata and has been functionally characterized. Experiments based on recombinant protein showed that the enzyme uses ω-hydroxy fatty acids or primary alcohols as its acyl acceptor and various hydroxycinnamoyl-CoAs—preferentially feruloyl-CoA and caffeoyl-CoA—as acyl donors at least in vitro. The transient expression of a MeHFT-GFP fusion transgene in the Nicotiana benthamiana leaf demonstrated that MeHFT is directed to the cytoplasm, suggesting that the feruloylation of cutin monomers takes place there.

  陆生植物的地上器官覆盖着一层疏水的保护性角质层。角质层的主要成分是脂质聚酯——角质，它由脂肪族和芳香族结构域组成。脂肪族部分是一种脂肪酸/醇和羟基肉桂酰酸之间的聚酯。BAHD/HxxxD家族酶是这些聚酯合成过程的核心。迄今为止，这类酶在苔藓植物中的性质尚未被探究。本文从地钱（Marchantium emarginatum）中分离出一个编码脂肪酸ω-羟酸/脂肪酸醇羟基肉桂酰转移酶（HFT）的基因，并进行了功能表征。基于重组蛋白的实验表明，该酶以ω-羟基脂肪酸或初级醇作为其酰基受体，以各种羟基肉桂酰-CoA——优选阿魏酰-CoA和咖啡酰-CoA——作为酰基供体，至少在体外如此。在地钱叶片中短暂表达MeHFT-GFP融合转基因表明，MeHFT被导向细胞质，这表明角质单体的阿魏化作用发生在那里。
• Enzymatic production of oroxylin A and hispidulin using a liverwort flavone 6-<i>O</i>-methyltransferase
  作者：Yu-Ying Zhang、Rui-Xue Xu、Shuai Gao、Ai-Xia Cheng

  DOI：10.1002/1873-3468.12312

  日期：2016.8

  its strongest preferences were baicalein and scutellarein, which were converted into, respectively, oroxylin A and hispidulin. Allowed a sufficient reaction time, the conversion rate of these two substrates was, respectively, 90% and 100%. PaF6OMT offers an enzymatic route to the synthesis of oroxylin A and hispidulin. This article is protected by copyright. All rights reserved.

  黄oxy属和地艾属物种中含量丰富的化合物Oroxylin A和组蛋白是治疗缺血性脑血管疾病的重要先导化合物。它们的酶促合成需要能够与相关类黄酮的6-OH基团相互作用的O-甲基转移酶，但是这种酶尚未在植物中鉴定出来。在此，从地艾属物种盲肠脉间裂中分离出编码O-甲基转移酶的基因（命名为PaF6OMT）。对替代底物的测试显示，其最强的偏好是黄ical素和黄cut苷，它们分别被转化为奥昔林A和组蛋白。在足够的反应时间下，这两种底物的转化率分别为90％和100％。PaF6OMT提供了一种酶促途径来合成羟丙草精A和组织蛋白。本文受版权保护。版权所有。
• Establishing a Toolkit for Precursor-Directed Polyketide Biosynthesis: Exploring Substrate Promiscuities of Acid-CoA Ligases
  作者：Maybelle Kho Go、Jeng Yeong Chow、Vivian Wing Ngar Cheung、Yan Ping Lim、Wen Shan Yew

  DOI：10.1021/bi300425j

  日期：2012.6.5

  biosynthesized from acyl-CoA precursors by polyketide synthases. One of the limitations to combinatorial biosynthesis of polyketides has been the lack of a toolkit that describes the means of delivering novel acyl-CoA precursors necessary for polyketide biosynthesis. Using five acid-CoA ligases obtained from various plants and microorganisms, we biosynthesized an initial library of 79 acyl-CoA thioesters by screening

  聚酮化合物是化学上多样化且具有医学上重要意义的生物化学物质，它们是通过聚酮化合物合酶从酰基辅酶A前体生物合成的。聚酮化合物的组合生物合成的局限性之一是缺少工具包，该工具包描述了递送聚酮化合物生物合成所必需的新型酰基-CoA前体的方法。使用从各种植物和微生物中获得的5种酸性CoA连接酶，我们通过针对123种羧酸的文库筛选每种酸性CoA连接酶，生物合成了79种酰基CoA硫酯的初始文库。酰基-CoA硫酯库包括肉桂基-CoA，3-苯基丙酰基-CoA，苯甲酰基-CoA，苯乙酰基-CoA，丙二酰-CoA，饱和和不饱和脂族CoA硫酯和双环芳族CoA硫酯的衍生物。在我们对新型酰基辅酶A前体的生物合成路线的搜索中，我们发现了两种以前未报道过的丙二酰辅酶A衍生物（3-硫代苯丙氨酰辅酶A和苯基丙二酰辅酶A），无法通过规范的丙二酰辅酶A合成酶生产。该报告强调了确定常规底物池之外底物混杂的实用性和重要性，并描述了建
• Cloning and Functional Characterization of Two 4-Coumarate: CoA Ligase Genes from Selaginella moellendorffii
  作者：Xin-Yan Liu、Ping-Ping Wang、Yi-Feng Wu、Ai-Xia Cheng、Hong-Xiang Lou

  DOI：10.3390/molecules23030595

  日期：——

  extensively characterized in other vascular plants, little is known of their functions in Selaginella. Here, we isolated two 4CL genes (Sm4CL1 and Sm4CL2) from Selaginella moellendorffii. Based on the enzymatic activities of the recombinant proteins, both of these genes encoded bona fide 4CLs. The 4CL isoforms in S. moellendorffii have different activities: Sm4CL2 was more active than Sm4CL1. The enzymatic properties

  卷柏是现存的苔藓双生植物属，代表了古代的气管植物谱系。重要的进化状态使其成为研究维管植物代谢进化的宝贵资源。4-香豆酸酯：CoA连接酶（4CL）是关键酶，它控制碳通过苯丙烷代谢途径进入特定的木质素，类黄酮和与壁结合的酚类生物合成途径的流量。尽管4CL在其他维管植物中已得到广泛表征，但对其在卷柏中的功能了解甚少。在这里，我们从卷柏卷柏中分离了两个4CL基因（Sm4CL1和Sm4CL2）。基于重组蛋白的酶活性，这两个基因均编码了真正的4CL。S. moellendorffii中的4CL亚型具有不同的活性：Sm4CL2比Sm4CL1更活跃。酶学性质和基因表达模式表明，4CL基因在维管植物的进化中是保守的。
• 4-Coumarate:coenzyme A ligase isoform 3 from <i>Piper nigrum</i> (Pn4CL3) catalyzes the CoA thioester formation of 3,4-methylenedioxycinnamic and piperic acids
  作者：Zhehao Jin、Juraithip Wungsintaweekul、Sang-Hoon Kim、Jeong-Han Kim、Yongho Shin、Dae-Kyun Ro、Soo-Un Kim

  DOI：10.1042/bcj20190527

  日期：2020.1.17

  enzyme, exhibited general 4CL activity towards coumaric and ferulic acids. However, Pn4CL3 was also active towards piperonylic acid, 3,4-MDCA, and piperic acid. Pn4CL3 possessed ∼2.6 times higher catalytic efficiency (kcat/KM) towards 3,4-MDCA and piperic acid than towards coumaric and ferulic acids, suggesting its specific role in piperine biosynthesis. Different substrate preference among the Pn4CL isoforms

  黑胡椒，Piper nigrum L.的干绿色水果，是世界上最受欢迎的家用香料。胡椒碱是黑胡椒的刺激性化合物，被认为部分源自苯丙烷途径。在胡椒碱的生物合成中，4-香豆酸酯：CoA连接酶（4CL）必须在将中间酸活化为相应的CoA硫酯作为底物方面发挥关键作用。基于转录组数据，我们从未成熟的胡椒中分离出三种黑假单胞菌4CL亚型（Pn4CL1，-2和-3）。这些Pn4CLs在大肠杆菌中表达，用于使用假定的底物，即肉桂酸，香豆酸，阿魏酸，胡椒基，3,4-亚甲基二氧肉桂酸（3,4-MDCA）和胡椒酸进行体外酶法测定。系统发育分析和底物使用研究表明，对香豆酸和阿魏酸有活性的Pn4CL1属于木质素合成的I类4CL。Pn4CL2是典型的肉桂酸酯特异的香豆酸盐：CoA连接酶样（CLL）蛋白。作为II类酶的Pn4CL3对香豆酸和阿魏酸具有一般的4CL活性。然而，Pn4CL3也对胡椒酸，3,4-MDCA和胡椒酸有活性。Pn4CL3对3