Indole-3-butanoate

• 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-butanoate
• 英文别名: 4-(1H-indol-3-yl)butanoate
• 化学式: C12H12NO2-
• 分子量: 202.23
• InChiKey: JTEDVYBZBROSJT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-butanoate 、 UDP-glucose 生成 4-(indol-3-yl)butanoyl-beta-D-glucose 、 UDP
  参考文献：
  名称：

  Perturbation of Indole-3-Butyric Acid Homeostasis by the UDP-GlucosyltransferaseUGT74E2ModulatesArabidopsisArchitecture and Water Stress Tolerance

  摘要：

  反应性氧化物和氧化还原信号与植物激素之间存在协同和拮抗相互作用，以调节植物对生物和非生物胁迫的保护反应。然而，对这种交互作用的分子机制了解甚少。我们证明，拟南芥的过氧化氢响应性UDP-葡糖苷转移酶UGT74E2参与了通过其对生长素吲哚-3-丁酸（IBA）的活性调节植物体型和水分胁迫响应。重组UGT74E2的生化特性表明，它强烈偏好IBA作为底物。在转基因植物中评估吲哚-3-乙酸（IAA）、IBA及其共轭物，表明催化特异性在植物体内得以维持。在这些转基因植物中，不仅IBA-Glc浓度增加，而且自由IBA水平升高，共轭IAA模式也被修改。这种扰动的IBA和IAA稳态与体型变化有关，包括增加的枝条分支和改变的莲座形状，并导致在干旱和盐胁迫处理期间显著提高了生存率。因此，我们的结果揭示了IBA和IBA-Glc是形态和生理应激适应机制的重要调节因子，并提供了氢过氧化物和生长素稳态之间相互作用的分子证据，通过IBA UGT的作用。

  DOI：

  10.1105/tpc.109.071316

文献信息

• Modification of auxinic phenoxyalkanoic acid herbicides by the acyl acid amido synthetase GH3.15 from Arabidopsis
  作者：Ashley M. Sherp、Soon Goo Lee、Evelyn Schraft、Joseph M. Jez

  DOI：10.1074/jbc.ra118.004975

  日期：2018.11

  corresponding auxinic phenoxyalkanoic acid herbicides 2,4-dichlorophenoxylacetic acid (2,4-D) and 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB). The IBA-specific AtGH3.15 protein displayed high catalytic activity with 2,4-DB, which was comparable to its activity with IBA. Screening of phenoxyalkanoic and phenylalkyl acids indicated that side-chain length of alkanoic and alkyl acids is a key feature of AtGH3.15's

  抗除草剂性状是最广泛使用的农业生物技术产品。然而，为了保持其有效性并减轻对除草剂抗性杂草的选择，发现使用不同化学作用方式的新抗性特征至关重要。在植物中，格雷琴·哈根（Gretchen Hagen）3（GH3）酰基酰胺合成酶催化氨基酸与茉莉酸酯和植物生长素的植物激素结合。尚未研究该反应化学作为除草剂修饰和灭活的可能方法。在这里，我们研究了一组使用生长素吲哚-3-乙酸（IAA）和吲哚-3-丁酸（IBA）作为底物的拟南芥GH3蛋白，以及相应的生长素苯氧基链烷酸除草剂2,4-二氯苯氧基乳酸（ 2,4-D）和4-（2,4-二氯苯氧基）丁酸（2,4-DB）。IBA特有的AtGH3.15蛋白对2,4-DB表现出高催化活性，这与其在IBA中的活性相当。苯氧基链烷酸和苯烷基酸的筛选表明，链烷酸和烷基酸的侧链长度是AtGH3.15底物偏爱的关键特征。AtGH3.15·2,4-DB配合物的X射线晶体结构揭示了除
• Arabidopsis thaliana GH3.15 acyl acid amido synthetase has a highly specific substrate preference for the auxin precursor indole-3-butyric acid
  作者：Ashley M. Sherp、Corey S. Westfall、Sophie Alvarez、Joseph M. Jez

  DOI：10.1074/jbc.ra118.002006

  日期：2018.3

  Various phytohormones control plant growth and development and mediate biotic and abiotic stress responses. Gretchen Hagen 3 (GH3) acyl acid amido synthetases are plant enzymes that typically conjugate amino acids to indole-3-acetic acid (IAA) or jasmonic acid (JA) to inactivate or activate these phytohormones, respectively; however, the physiological and biological roles of many of these enzymes remain unclear. Using a biochemical approach, we found that the Arabidopsis thaliana GH3.15 (AtGH3.15) preferentially uses indole-3-butyric acid (IBA) and glutamine as substrates. The X-ray crystal structure of the AtGH3.15 center dot AMP complex, modeling of IBA in the active site, and biochemical analysis of site-directed mutants provide insight on active site features that lead to AtGH3.15's preference for IBA. Assay-based in planta analysis of AtGH3.15-overexpressing lines indicated that their root elongation and lateral root density were resistant to IBA treatment but not to treatment with either IAA or JA. These findings suggest that AtGH3.15 may play a role in auxin homeostasis by modulating the levels of IBA for peroxisomal conversion to IAA. Analysis of AtGH3.15 promoter-driven yellow fluorescent protein reporter lines revealed that AtGH3.15 is expressed at significant levels in seedlings, roots, and parts of the siliques. We conclude that AtGH3.15 is unique in the GH3 protein family for its role in modifying IBA in auxin homeostasis and that it is the first GH3 protein shown to primarily modify a plant growth regulator other than IAA and JA.