S-[2-[3-[[(2R)-4-[[[(2R,3R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基](E)-十四碳-11-烯硫代羧酸酯 | 53034-79-0

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: S-[2-[3-[[(2R)-4-[[[(2R,3R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基](E)-十四碳-11-烯硫代羧酸酯
• 中文别名: S-{17-[(2R,3S,4R,5R)-5-(6-氨基-9H-嘌呤-9-基)-4-羟基-3-(磷羧基氧代)四氢呋喃-2-基]-9,13,15-三羟基-10,10-二甲基-13,15-二羟基-4,8-二羰基-12,14,16-三氧杂-3,7-二氮杂-13,15-二磷杂十七碳-1-基}(2E)-3-(3,4-二羟基苯基)丙-2-烯硫酸酯
• 英文名称: caffeoyl 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-(3,4-dihydroxyphenyl)prop-2-enethioate
• CAS: 53034-79-0
• 化学式: C₃₀H₄₂N₇O₁₉P₃S
• 分子量: 929.686
• InChiKey: QHRGJMIMHCLHRG-FUEUKBNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  429
• 氢给体数：
  11
• 氢受体数：
  24

安全信息

• 储存条件：
  -20°C

制备方法与用途

咖啡酰辅酶A可以从禾本科植物的叶组织中分离出来，其Km值为1.45微摩尔。

反应信息

• 作为反应物：
  描述：

  S-[2-[3-[[(2R)-4-[[[(2R,3R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基](E)-十四碳-11-烯硫代羧酸酯 在 hydroxycinnamic acids/hydroxycinnamoyl CoA esters O-methyltransferase 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
• 作为产物：
  描述：

  咖啡酸 在 4-coumarate-CoA ligase 作用下， 生成 S-[2-[3-[[(2R)-4-[[[(2R,3R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基](E)-十四碳-11-烯硫代羧酸酯
  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

• 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。
• 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。
• Characterization and Functional Analysis of 4-Coumarate:CoA Ligase Genes in Mulberry
  作者：Chuan-Hong Wang、Jian Yu、Yu-Xiang Cai、Pan-Pan Zhu、Chang-Ying Liu、Ai-Chun Zhao、Rui-Hua Lü、Meng-Jiao Li、Feng-Xiang Xu、Mao-De Yu

  DOI：10.1371/journal.pone.0155814

  日期：——

  A small, multigene family encodes 4-coumarate:CoA ligases (4CLs) that catalyze the ligation of CoA to hydroxycinnamic acids, a branch point directing metabolites to flavonoid or monolignol pathways. In this study, we characterized four 4CL genes from M. notabilis Genome Database, and cloned four Ma4CL genes from M. atropurpurea cv. Jialing No.40. A tissue-specific expression analysis indicated that Ma4CL3 was expressed at higher levels than the other genes, and that Ma4CL3 was strongly expressed in root bark, stem bark, and old leaves. Additionally, the expression pattern of Ma4CL3 was similar to the trend of the total flavonoid content throughout fruit development. A phylogenetic analysis suggested that Mn4CL1, Mn4CL2, and Mn4CL4 belong to class I 4CLs, and Mn4CL3 belongs to class II 4CLs. Ma4CL genes responded differently to a series of stresses. Ma4CL3 expression was higher than that of the other Ma4CL genes following wounding, salicylic acid, and ultraviolet treatments. An in vitro enzyme assay indicated that 4-coumarate acid was the best substrate among cinnamic acid, 4-coumarate acid, and caffeate acid, but no catalytic activity to sinapate acid and ferulate acid. The results of subcellular localization experiments showed that Ma4CL3 localized to the cytomembrane, where it activated transcription. We used different vectors and strategies to fuse Ma4CL3 with stilbene synthase (STS) to construct four Ma4CL-MaSTS co-expression systems to generate resveratrol. The results indicated that only a transcriptional fusion vector, pET-Ma4CL3-T-MaSTS, which utilized a T7 promoter and lac operator for the expression of MaSTS, could synthesize resveratrol.

  一个由多个基因组成的小家族编码4-香豆酸：辅酶A连接酶（4CL），该酶催化辅酶A与羟基肉桂酸的连接，这是将代谢物导向黄酮或单木酚途径的分叉点。在这项研究中，我们描述了来自M. notabilis基因组数据库的四个4CL基因，并克隆了来自M. atropurpurea cv. Jialing No.40的四个Ma4CL基因。组织特异性表达分析表明，Ma4CL3的表达水平高于其他基因，并且在根皮、茎皮和旧叶中表达强烈。此外，Ma4CL3的表达模式与整个果实发育过程中总黄酮含量的趋势相似。系统发育分析表明，Mn4CL1、Mn4CL2和Mn4CL4属于I类4CL，而Mn4CL3属于II类4CL。Ma4CL基因对一系列胁迫的反应不同。在伤口、水杨酸和紫外线处理后，Ma4CL3的表达水平高于其他Ma4CL基因。体外酶分析表明，在肉桂酸、4-香豆酸和咖啡酸中，4-香豆酸是最好的底物，但对芥酸和阿魏酸没有催化活性。亚细胞定位实验结果表明，Ma4CL3定位于细胞膜，并在那里激活转录。我们使用不同的载体和策略将Ma
• Facile enzymic synthesis of caffeoyl CoA
  作者：Huabin Meng、Wilbur H. Campbell

  DOI：10.1016/s0031-9422(96)00594-8

  日期：1997.2

  p-Hydroxycinnamic acid:CoA ligase (EC 6.2.1.12) was extracted from aspen xylem and its activity with several cinnamic acids was determined. The highest activity was found with p-hydroxycinnamic acid and the extract had reasonable activity with ferulic, caffeic and 5-hydroxyferulic acids but none with sinapic acid. Using this isolated enzyme preparation, caffeoyl CoA was synthesized and subsequently purified using reversed phase C-18 solid phase extraction. This enzymic synthesis method, which yielded 40% product, is rapid and simple and provides a cost-effective alternative to the use of commercial acyl CoA ligase. Copyright (C) 1997 Elsevier Science Ltd.
• Physicochemical properties, antioxidant activities and comprehensive phenolic profiles of tea-macerated Chardonnay wine and model wine
  作者：Zijian Liang、Pangzhen Zhang、Wen Ma、Xin-An Zeng、Zhongxiang Fang

  DOI：10.1016/j.foodchem.2023.137748

  日期：2024.3