indole-3-acetate | 1596-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: indole-3-acetate
• 英文别名: 3-indoleacetate；indoleacetate；I3AT；2-(1H-indol-3-yl)acetate
• CAS: 1596-90-3
• 化学式: C₁₀H₈NO₂
• 分子量: 174.179
• InChiKey: SEOVTRFCIGRIMH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  indole-3-acetate 在 1,4-dithio-D,L-threitol 、 His₆-tagged recombinant indoleacetate decarboxylase from Olsenella uli activating enzyme 、 His₆-tagged recombinant indoleacetate decarboxylase from Olsenella uli 、 5-脱氮核黄素 作用下， 以 aq. buffer 为溶剂， 生成 3-甲基吲哚
  参考文献：
  名称：

  形成粪臭素的甘氨酰自由基酶的机理研究表明反应通过氢原子转移引发

  摘要：

  氨基酸衍生的芳基乙酸酯的肠道微生物脱羧是一种化学上具有挑战性的酶促转化，它会产生影响宿主生理的小分子。来自Olsenella uli ( Ou IAD)的甘氨酰自由基酶 (GRE) 吲哚乙酸脱羧酶对 indole-3-acetate (I3A) 进行非氧化性自由基脱羧，产生粪臭素，这是一种在猪和反刍动物肠道中产生的与疾病相关的代谢物。尽管 IAD 很重要，但我们对其机制的理解是有限的。在这里，我们描述了Ou IAD 的机制，评估了先前提出的假设：（1）涉及初始 1-e 的 Kolbe 型脱羧反应-I3A 的羧酸盐的氧化或 (2) 从 I3A 的 α-碳中提取氢原子以产生初始的以碳为中心的自由基。定点诱变、动力学同位素效应实验、在 D 2 O 中进行的反应分析和计算建模与涉及初始氢原子转移的机制一致。这一发现更广泛地扩展了 GRE 脱羧酶和非氧化性脱羧酶所采用的自由基机制的类型。阐明 IAD

  DOI：

  10.1021/jacs.1c13580
• 作为产物：
  描述：

  吲哚-3-乙腈 、 水 生成 indole-3-acetate 、 铵
  参考文献：
  名称：

  Characterization of a Nitrilase and a Nitrile Hydratase from Pseudomonas sp. Strain UW4 That Converts Indole-3-Acetonitrile to Indole-3-Acetic Acid

  摘要：

  摘要 吲哚-3-乙酸（IAA）是一种基本的植物激素，能够控制植物生长和发育的许多方面。 假单胞菌 菌株 UW4 是一种根瘤植物生长促进细菌，能产生和分泌 IAA。虽然该细菌中有多个推定的 IAA 生物合成基因，但导致菌株 UW4 产生 IAA 的途径尚不清楚。本文描述了 IAA 生物合成的吲哚-3-乙酰胺（IAM）和吲哚-3-乙醛肟/吲哚-3-乙腈（IAOx/IAN）途径，并评估了介导这些途径的两种酶（硝化酶和腈氢化酶）的具体作用。编码这两种酶的基因在 大肠杆菌 中表达，并分离和鉴定了这两种酶。底物进食试验表明，腈水解酶从 IAN 底物中产生 IAM 和 IAA，而腈水解酶只产生 IAM。这两种腈水解酶的最适温度和 pH 值截然不同。腈水解酶最适温度为 50°C，pH 值为 6；而腈水解酶最适温度为 4°C，pH 值为 7.5。根据多序列比对、主题分析、理化性质和酶测定，可以得出结论：UW4 腈酶具有芳香底物特异性。腈水解酶被确定为一种铁型金属酶，不需要 P47K 激活蛋白的帮助就能发挥活性。这些数据被解释为该细菌中 IAA 生物合成的初步模型。

  DOI：

  10.1128/aem.00649-14

文献信息

• First Micelle-Free Photoredox Catalytic Access to Hydrated Electrons for Syntheses and Remediations with a Visible LED or even Sunlight
  作者：Robert Naumann、Martin Goez

  DOI：10.1002/chem.201803929

  日期：2018.11.27

  sustainability and applications, we have instead attached carboxylate groups to a ruthenium (tris)bipyridyl catalyst such that its pentaanionic radical strongly repels the dianionic radical of the bioavailable donor urate. We have explored the influence of the Coulombic interactions on the electron generation by a time‐resolved study from microseconds to hours, including for comparison the unsubstituted complex

  水合电子是超还原剂，但是当两个光子汇聚在一起时，可见光可以生成可见光，最有效的方式是将第一光子的能量存储在自由基对中，该自由基对是由牺牲供体还原激发的催化剂而形成的。以前所有此类用于在可见光范围内产生可合成数量的带电子的水合电子的系统，都必须借助SDS胶束进行分隔，以限制该对的性能受限重组。为了克服胶束对可持续性和应用的限制，我们将羧酸酯基团连接到钌（tris）联吡啶基催化剂上，以使其五阴离子基团强烈排斥生物可利用的供体尿酸盐的二阴离子基团。我们通过时间分辨研究（从微秒到几小时）探索了库仑相互作用对电子生成的影响，包括进行比较，形成未取代的复合物，形成单阳离子自由基，带有或不带有SDS胶束。就稳定性和总电子输出而言，新的均匀电子源是最好的。它的合成范围更广，因为它不需要胶束屏蔽亲水性较低的化合物，这特别有利于交叉偶联。它可以耐受超分子容器作为水不溶性底物或产品的载体。作为该领域的一项应用，
• An in Vitro System of Indole-3-Acetic Acid Formation from Tryptophan in Maize (Zea mays) Coleoptile Extracts
  作者：T. Koshiba、H. Matsuyama

  DOI：10.1104/pp.102.4.1319

  日期：1993.8.1

  The formation of a product from tryptophan that had the same retention time as that of authentic indole-3-acetic acid (IAA) on high performance liquid chromatography was detected in crude extracts of maize (Zea mays) coleoptiles. The product was identified as IAA by mass spectrometry. The IAA-forming activity was co-purified with an indole-3-acetaldehyde (IAAld) oxidase activity by chromatography on hydrophobic and gel filtration (GPC-100) columns. During purification, the IAA-forming activity, rather than that of IAAld oxidase, decreased; but when hemoprotein obtained from the same tissue was added, activity recovered to the same level as that of IAAld oxidase. The promotive activity of the hemoprotein was confirmed by the result that the activity coincided with amounts of the hemoprotein after GPC-100 column chromatography. The hemoprotein was characterized and identified as a cytosolic ascorbate peroxidase (T. Koshiba [1993] Plant Cell Physiol [in press]). The reaction of the IAA-forming activity was apparently one step from tryptophan. The activity was inhibited by 2-mercaptoethanol. The optimum temperature for the IAA-forming system as well as for the IAAld oxidase was 50 to 60[deg]C, and the acitivity at 30[deg]C was one-third to one-half of that at 60[deg]C. The system did not discriminate the L- and D-enantiomers of tryptophan.

  在玉米胚芽的粗提物中，检测到了由色氨酸形成的产品，其在高效液相色谱法上的保留时间与真正的吲哚-3-乙酸（IAA）相同。通过质谱法，该产品被鉴定为IAA。通过疏水色谱和凝胶过滤色谱（GPC-100）柱，IAA形成活性与吲哚-3-乙醛（IAAld）氧化酶活性共同纯化。在纯化过程中，IAA形成活性（而非IAAld氧化酶活性）下降；但当加入从相同组织获得的血红蛋白时，活性恢复到与IAAld氧化酶相同的水平。血红蛋白的促进活性通过以下结果得到证实：在GPC-100柱色谱法后，活性与血红蛋白的量一致。血红蛋白的特征和鉴定为细胞质抗坏血酸过氧化物酶（T. Koshiba [1993] Plant Cell Physiol [in press]）。IAA形成活性的反应显然是从色氨酸一步完成的。该活性被2-巯基乙醇抑制。IAA形成系统和IAAld氧化酶的最佳温度为50至60[deg]C，30[deg]C时的活性是60[deg]C时的三分之一到一半。该系统不能区分色氨酸的L-和D-对映体。
• Molecular Cloning and Characterization of Aldehyde Oxidases in Arabidopsis thaliana
  作者：H. Sekimoto、M. Seo、N. Kawakami、T. Komano、S. Desloire、S. Liotenberg、A. Marion-Poll、M. Caboche、Y. Kamiya、T. Koshiba

  DOI：10.1093/oxfordjournals.pcp.a029387

  日期：1998.4.1

  Using degenerate primers designed by deduced amino acid sequences of known aldehyde oxidases (AO) from maize and bovine, two independent cDNA fragments were amplified by reverse transcription-polymerase chain reaction (PCR). The two corresponding full-length cDNAs (atAO-1 and atAO-2; 4,484 and 4,228 bp long, respectively) were cloned by screening the Arabidopsis cDNA library followed by rapid amplification of cDNA end-PCR. These cDNAs are highly homologous at both the nucleotide and amino acid sequence levels, and the deduced amino acid sequences showed high similarity with those of maize and tomato AOs. They contain consensus sequences for two iron-sulfur centers and a molybdenum cofactor (MoCo)-binding domain. In addition, another cDNA having a sequence similar to that of the cDNAs was screened (atAO-3; 3,049 bp), and a putative AO gene (AC002376) was reported on chromosome 1, which (atAO-4) was distinct from, but very similar to, the above three AOs. atAO-1, 2, 3, and 4 were physically mapped on chromosomes 5, 3, 2 and 1, respectively. These data indicate that there is an AO multigene family in Arabidopsis. atAO-1 protein was shown to be highly similar to one of the maize AOs in respect to a region thought to be involved in determination of substrate specificity, suggesting that they might encode a similar type of AO, which could efficiently oxidize indole-3-acetaldehyde to indole-3-acetic acid (IAA). atAO-1 and atAO-2 genes were expressed at higher levels in lower hypo-cotyls and roots of the wild-type seedlings, while atAO-3 was slightly higher in cotyledons and upper hypocotyls. The expression of atAO-1 was more abundant in the seedlings of an IAA overproducing mutant (superrootl; surf) than in those of wild type. atAO-2 and atAO-3 transcripts were rather evenly distributed in these seedlings. A possible involvement of atAO genes in phytohormone biosynthesis in Arabidopsis is discussed.

  利用根据玉米和牛已知醛氧化酶（AO）氨基酸序列设计的退化引物，通过反转录聚合酶链反应（PCR）扩增出两个独立的 cDNA 片段。通过筛选拟南芥 cDNA 文库，然后快速扩增 cDNA end-PCR，克隆出了两个相应的全长 cDNA（atAO-1 和 atAO-2；分别长 4,484 和 4,228 bp）。这些 cDNA 在核苷酸和氨基酸序列水平上高度同源，推导出的氨基酸序列与玉米和番茄 AOs 的氨基酸序列高度相似。它们包含两个铁硫中心和一个钼辅助因子（MoCo）结合域的共识序列。此外，还筛选出另一个与上述 cDNA 序列相似的 cDNA（atAO-3；3,049 bp），并在 1 号染色体上报告了一个推测的 AO 基因（AC002376），该基因（atAO-4）与上述三个 AO 不同，但非常相似。这些数据表明拟南芥中存在一个 AO 多基因家族。atAO-1 蛋白与玉米中的一种 AO 在一个被认为参与确定底物特异性的区域上高度相似，这表明它们可能编码一种类似的 AO，能有效地将吲哚-3-乙醛氧化成吲哚-3-乙酸（IAA）。在野生型幼苗的下胚轴和根中，atAO-1 和 atAO-2 基因的表达量较高，而在子叶和上胚轴中，atAO-3 的表达量稍高。在IAA过量产生的突变体（superrootl；surf）的幼苗中，atAO-1的表达量比野生型高。本文讨论了atAO基因参与拟南芥植物激素生物合成的可能性。
• Production of Homo- and Hetero-Dimeric Isozymes from Two Aldehyde Oxidase Genes of Arabidopsis thaliana
  作者：S. Akaba、M. Seo、N. Dohmae、K. Takio、H. Sekimoto、Y. Kamiya、N. Furuya、T. Romano、T. Koshiba

  DOI：10.1093/oxfordjournals.jbchem.a022463

  日期：1999.8.1

  Polyclonal antibodies were raised against synthetic peptides or recombinant polypeptides encoded by Arabidopsis atAO-1 and atAO-2 cDNAs, which have sequences similar to maize and animal aldehyde oxidase (AO) cDNAs. Anti-atAO-1 antibodies recognized AOa and A0β among the three isoforms, AOα, AOβ, and AOγ, detected in Arabidopsis seedlings after native PAGE, while anti-atAO-2 antibodies reacted with AOβ and AOγ. The polypep-tide specifically recognized by each antibody was collected as the Protein-A/IgG/antigen complex. The 150- and 146-kDa polypeptides were purified by SDS-PAGE and digested with Achromobacter Protease I. From the amino acid sequences and molecular masses of the derivative peptides, it was revealed that the 150- and 145-kDa polypeptides were the products of atAO-1 and atAO-2, respectively. Molecular masses of the native forms of AOα, AOβ, and AOγ were estimated as approximately 290–300 kDa. These results suggest that AOα and AOγare homodimers consisting of atAO-1 and atAO-2 products, respectively, and that AOβ is a heterodimer of the atAO-1 and atAO-2 products.

  针对由拟南芥atAO-1和atAO-2 cDNAs编码的合成肽或多肽，我们制备了多克隆抗体，这些多肽的序列与玉米和动物醛氧化酶（AO）cDNA的序列相似。抗atAO-1抗体在原位PAGE后检测到拟南芥幼苗中的三种同工型AOα、AOβ和AOγ中的AOa和A0β，而抗atAO-2抗体与AOβ和AOγ反应。每种抗体特异性识别的多肽作为蛋白质A/IgG/抗原复合物收集。150和146 kDa的多肽通过SDS-PAGE纯化，并用Achromobacter蛋白酶I消化。从衍生的肽的氨基酸序列和分子质量来看，150和145 kDa的多肽分别是atAO-1和atAO-
• Functional Expression of Two Arabidopsis Aldehyde Oxidases in the Yeast Pichia pastoris
  作者：H. Koiwai、S. Akaba、M. Seo、T. Komano、T. Koshiba

  DOI：10.1093/oxfordjournals.jbchem.a022654

  日期：2000.4.1

  To investigate the biochemical and enzymatic properties of two aldehyde oxidase (AO) isoforms of Arabidopsis thaliana, we expressed AAO1 and AAO2 cDNAs in a heterolo-gous yeast (Pichia pastoris) system and successfully obtained the proteins in active forms. The expressed AAO1 and AAO2 proteins gave activity bands with the same mobilities on native gel electrophoresis and exhibited the same substrate preferences on zymograms with 8 aldehydes as those of AOa and AOy in Arabidopsis seedlings, respectively. Furthermore, anti-AAO1 and anti-AAO2 antibodies, which specifically recognize the seedling AOα and AOγ, respectively, reacted with the AAO1 and AAO2 proteins produced in P. pastoris, respectively. These results indicate that these AO proteins are accurately produced in the yeast system, as in Arabidopsis seedlings. Using AO preparations from P. pastoris, the enzymatic properties of Arabidopsis AOα and AOγ were investigated. AOα showed a relatively wide substrate specificity for 7 aldehydes tested, with high affinity to benzaldehyde and indole-3-aldehyde, while AOγ could most efficiently oxidize naphthaldehyde. AOα was strongly inhibited by iodoacetate and KCN, while AOγ was inhibited not only by iodoacetate and KCN but also by 2-mercaptethanol, dithiothreitol, menadion, and estradiol. AOα and AOγ showed the highest activity at around 65 and 50°C, respectively, and exhibited pH dependence around pH 8.0. These results indicate that the two AO isoforms in Arabidopsis seedlings have different enzymatic properties and may have different physiological roles in vivo.

  为了研究拟南芥两种醛氧化酶（AO）异构体的生化和酶学特性，我们在异源酵母（Pichia pastoris）系统中表达了 AAO1 和 AAO2 cDNA，并成功获得了活性形式的蛋白质。表达的 AAO1 和 AAO2 蛋白在原生凝胶电泳中呈现出相同迁移率的活性条带，并且在 8 种醛的酶图谱中表现出与拟南芥幼苗中的 AOa 和 AOy 相同的底物偏好。此外，抗 AAO1 和抗 AAO2 抗体分别能特异性识别拟南芥幼苗中的 AOα 和 AOγ，它们也能分别与拟南芥中产生的 AAO1 和 AAO2 蛋白发生反应。这些结果表明，与拟南芥幼苗一样，这些 AO 蛋白也是在酵母系统中准确产生的。利用拟南芥的 AO 制剂，研究了拟南芥 AOα 和 AOγ 的酶特性。AOα 对所测试的 7 种醛具有相对广泛的底物特异性，对苯甲醛和吲哚-3-甲醛具有较高的亲和力，而 AOγ 能最有效地氧化萘甲醛。AOα 受碘乙酸酯和 KCN 的强烈抑制，而 AOγ 不仅受碘乙酸酯和 KCN 的抑制，还受 2-巯基乙醇、二硫苏糖醇、甲萘醌和雌二醇的抑制。AOα 和 AOγ 分别在 65 和 50°C 左右显示出最高的活性，并在 pH 8.0 左右表现出 pH 依赖性。这些结果表明，拟南芥幼苗中的两种 AO 异构体具有不同的酶特性，在体内可能具有不同的生理作用。