(+)-7-iso-jasmonoyl-L-isoleucine | 145414-77-3

• 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
• 英文名称: (+)-7-iso-jasmonoyl-L-isoleucine
• 英文别名: Ja-Ile；N-({(1r,2s)-3-Oxo-2-[(2z)-Pent-2-En-1-Yl]cyclopentyl}acetyl)-L-Isoleucine；(2S,3S)-3-methyl-2-[[2-[(1R,2S)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetyl]amino]pentanoic acid
• CAS: 145414-77-3
• 化学式: C₁₈H₂₉NO₄
• 分子量: 323.433
• InChiKey: IBZYPBGPOGJMBF-QPERPISQSA-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：

  (+)-7-iso-jasmonoyl-L-isoleucine 在 CYP₉₄B₃ 作用下， 以 甘油 为溶剂， 反应 120.0h， 生成 N-({(1R)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl}acetyl)-L-isoleucine
  参考文献：
  名称：

  CYP94B3 activity against jasmonic acid amino acid conjugates and the elucidation of 12-O-β-glucopyranosyl-jasmonoyl-l-isoleucine as an additional metabolite

  摘要：

  The hormonal action of jasmonate in plants is controlled by the precise balance between its biosynthesis and inactivation. Oxidation of jasmonoyl-L-isoleucine at the C-12 position, which is catalyzed by cytochrome P450s CYP94B3 and CYP94C1, is thought to be one of the main inactivation pathways. In this study, an additional function of CYP94B3 was elucidated, as well additional jasmonoyl-L-isoleucine metabolites being investigated. It was found that CYP94B3 also catalyzes the hydroxylation of jasmonoyl-L-valine and jasmonoyl-L-phenylalanine, and that these hydroxyl compounds accumulated after wounding and possessed lower activity than non-hydroxylated compounds. Additionally, 12-O-beta-glucopyranosyl-jasmonoyl-t-isoleucine accumulated after wounding, suggesting that it is a metabolite of

  DOI：

  10.1016/j.phytochem.2013.12.019
• 作为产物：
  描述：

  (2S,3S)-2-(2-((1R,2S,3R)-3-hydroxy-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetamido)-3-methylpentanoic acid 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以100%的产率得到(+)-7-iso-jasmonoyl-L-isoleucine
  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

• [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。
• Design and synthesis of biotin-tagged photoaffinity probes of jasmonates
  作者：Min Gu、Jianbin Yan、Zhiyan Bai、Yue-Ting Chen、Wei Lu、Jie Tang、Liusheng Duan、Daoxin Xie、Fa-Jun Nan

  DOI：10.1016/j.bmc.2010.03.059

  日期：2010.5

  Jasmonates (JAs) are a class of oxylipin compounds that play diverse roles in plant defense and development. The F-box protein coronatine insensitive1 (COI1) plays a crucial role in the JA signaling pathway. To determine whether COI1 binds directly to jasmonates, three biotin-tagged photoaffinity probes for JAs, a jasmonic acid photoaffinity probe (PAJA), a JAIle photoaffinity probe (PAJAIle), and a coronatine photoaffinity probe (PACOR), were designed and synthesized based on analysis of JA structure-activity relationships and molecular modeling of the interaction between COI1 and JAs. Among them, PACOR exhibited the most significant biological activity in inhibiting root growth, promoting accumulation of JA-responsive proteins, and triggering COI1-JAZ1 interaction in Arabidopsis seedlings. PACOR is an effective tool for elucidating the interaction between COI1 and JA. (c) 2010 Elsevier Ltd. All rights reserved.
• 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.
• CYP94B3 activity against jasmonic acid amino acid conjugates and the elucidation of 12-O-β-glucopyranosyl-jasmonoyl-l-isoleucine as an additional metabolite
  作者：Naoki Kitaoka、Hiroshi Kawaide、Naruki Amano、Takuya Matsubara、Kensuke Nabeta、Kosaku Takahashi、Hideyuki Matsuura

  DOI：10.1016/j.phytochem.2013.12.019

  日期：2014.3

  The hormonal action of jasmonate in plants is controlled by the precise balance between its biosynthesis and inactivation. Oxidation of jasmonoyl-L-isoleucine at the C-12 position, which is catalyzed by cytochrome P450s CYP94B3 and CYP94C1, is thought to be one of the main inactivation pathways. In this study, an additional function of CYP94B3 was elucidated, as well additional jasmonoyl-L-isoleucine metabolites being investigated. It was found that CYP94B3 also catalyzes the hydroxylation of jasmonoyl-L-valine and jasmonoyl-L-phenylalanine, and that these hydroxyl compounds accumulated after wounding and possessed lower activity than non-hydroxylated compounds. Additionally, 12-O-beta-glucopyranosyl-jasmonoyl-t-isoleucine accumulated after wounding, suggesting that it is a metabolite of