(±)-茉莉酸-异亮氨酸 | 120330-93-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (±)-茉莉酸-异亮氨酸
• 英文名称: N-((-)-jasmonoyl)-L-isoleucine
• 英文别名: (-) jasmonoyl-L-isoleucine；(-)-jasmonoyl-L-isoleucine；(2S,3S)-3-methyl-2-[[2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetyl]amino]pentanoic acid
• CAS: 120330-93-0
• 化学式: C₁₈H₂₉NO₄
• 分子量: 323.433
• InChiKey: IBZYPBGPOGJMBF-QRHMYKSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲氧基胺盐酸盐 、 (±)-茉莉酸-异亮氨酸 以 甲醇 、 水 为溶剂， 反应 18.0h， 以71.429%的产率得到
  参考文献：
  名称：

  [EN] COMPOUNDS AND THEIR USE AS ANTAGONISTS OF JASMONATE PERCEPTION
  [FR] COMPOSÉS ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DE PERCEPTION DE JASMONATE

  摘要：

  这项发明提供了适用于改变植物、种子或从种子生长出来的植物特性的化合物、方法和用途，通过抑制植物中茉莉酸介导的过程。特别地，该发明提供了茉莉酸类似物或其他结构相关的类似物，其作为拮抗剂发挥作用。例如，它们可以用于提高植物对一种或多种生物性或半生物性病原体的抗病能力，或用于提高植物对非生物胁迫的抗性。

  公开号：

  WO2015040061A1
• 作为产物：
  描述：

  N-[2-[(1R,2R,3S)-3-Hydroxy-2-(2Z)-2-penten-1-ylcyclopentyl]acetyl]-L-isoleucine 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 以89%的产率得到(±)-茉莉酸-异亮氨酸
  参考文献：
  名称：

  Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid

  摘要：

  The TES ether of 2-((1R,2S,3R)-3-hydroxy-2-((Z)-pent-2-enyl)cyclopentyl)acetic acid (5, equal to the reduction product of epi-jasmonic acid) derived from (1R,4S)-4-hydroxycyclopent-2-enyl acetate (19) in 13 steps was activated by using isobutyl chloroformate and was subjected to condensation with isoleucine at room temperature for 48 h. The product was desilylated and oxidized to the isoleucine conjugate of epi-jasmonic acid in 68% yield over three steps. Similarly, allo-isoleucine conjugate of epi-jasmonic acid and three isoleucine conjugates of ent-epi-jasmonic acid, jasmonic acid, and ent-jasmonic acid were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.144

文献信息

• Preparation and Biological Activity of Molecular Probes to Identify and Analyze Jasmonic Acid-binding Proteins
  作者：Yusuke JIKUMARU、Tadao ASAMI、Hideharu SETO、Shigeo YOSHIDA、Tadashi YOKOYAMA、Naomi OBARA、Morifumi HASEGAWA、Osamu KODAMA、Makoto NISHIYAMA、Kazunori OKADA、Hideaki NOJIRI、Hisakazu YAMANE

  DOI：10.1271/bbb.68.1461

  日期：2004.1

  Several types of jasomonic acid (JA) derivatives, including JA–amino acid conjugates, a JA–biotin conjugate, a JA–dexamethasone heterodimer, and a JA–fluoresceine conjugate, were prepared as candidates for molecular probes to identify JA-binding proteins. These JA derivatives, excepting the JA–fluoresceine conjugate, exhibited significant biological activities in a rice seedling assay, a rice phytoalexin-inducing assay, and/or a soybean phenylalanine ammonia-lyase-inducing assay. These JA derivatives could therefore be useful probes for identifying JA-binding proteins. The activity spectra of the prepared compounds were different from each other, suggesting that different types of JA receptors were involved in the perception of JA derivatives in the respective bioassays.

  几种类型的茉莉酸（JA）衍生物被制备为识别JA结合蛋白的分子探针候选者，包括JA-氨基酸结合物、JA-生物素结合物、JA-氟莱赛因结合物和JA-地塞米松异二聚体。这些JA衍生物（排除JA-氟莱赛因结合物）在水稻幼苗测定、水稻植物防御素诱导测定和/或大豆苯丙氨酸氨解酶诱导测定中表现出显著的生物活性。因此，这些JA衍生物可以作为识别JA结合蛋白的有用探针。所制备化合物的活性谱各不相同，表明在各自的生物测定中涉及了不同类型的JA受体对JA衍生物的感知。
• STRUCTURALLY MODIFIED COI1
  申请人：Board of Trustees of Michigan State University

  公开号：US20180135070A1

  公开（公告）日：2018-05-17

  Described herein are plants that are resistant to herbicides, such as herbicide compositions comprising coronatine, where the herbicide-resistant plants express a modified CORONATINE INSENSITIVE 1 (COI1) protein.
• Strategy for synthesis of the isoleucine conjugate of epi-jasmonic acid
  作者：Narihito Ogawa、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2008.09.144

  日期：2008.12

  The TES ether of 2-((1R,2S,3R)-3-hydroxy-2-((Z)-pent-2-enyl)cyclopentyl)acetic acid (5, equal to the reduction product of epi-jasmonic acid) derived from (1R,4S)-4-hydroxycyclopent-2-enyl acetate (19) in 13 steps was activated by using isobutyl chloroformate and was subjected to condensation with isoleucine at room temperature for 48 h. The product was desilylated and oxidized to the isoleucine conjugate of epi-jasmonic acid in 68% yield over three steps. Similarly, allo-isoleucine conjugate of epi-jasmonic acid and three isoleucine conjugates of ent-epi-jasmonic acid, jasmonic acid, and ent-jasmonic acid were synthesized. (C) 2008 Elsevier Ltd. All rights reserved.
• [EN] COMPOUNDS AND THEIR USE AS ANTAGONISTS OF JASMONATE PERCEPTION<br/>[FR] COMPOSÉS ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DE PERCEPTION DE JASMONATE
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2015040061A1

  公开（公告）日：2015-03-26

  The invention provides compounds, methods and uses suitable for modifying the characteristics of a plant, seed, or plant grown from the seed, by inhibiting jasmonate-mediated processes in the plant. In particular the invention provides jasmonate analogs, or other structurally related analogs, which function as antagonists. These can be used, for example, for improving disease resistance against one or more biotrophic or hemi-biotrophic pathogens, or for improving resistance against abiotic stress.

  这项发明提供了适用于改变植物、种子或从种子生长出来的植物特性的化合物、方法和用途，通过抑制植物中茉莉酸介导的过程。特别地，该发明提供了茉莉酸类似物或其他结构相关的类似物，其作为拮抗剂发挥作用。例如，它们可以用于提高植物对一种或多种生物性或半生物性病原体的抗病能力，或用于提高植物对非生物胁迫的抗性。