(+)-2',3'-dihydro-2'α,3'α-epoxyabscisic acid | 164854-64-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-2',3'-dihydro-2'α,3'α-epoxyabscisic acid
• 英文别名: 2'α,3'α-epoxyabscisic acid；2'alpha,3'alpha-Dihydro-2'alpha,3'alpha-epoxy-abscisic acid；(2Z,4E)-5-[(1R,2S,6S)-2-hydroxy-1,3,3-trimethyl-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]-3-methylpenta-2,4-dienoic acid
• CAS: 164854-64-2
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: LTFJVAGATJTPPP-ZNDSGQFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-2',3'-dihydro-2'α,3'α-epoxyabscisic acid 在 copper(l) iodide 、 氢溴酸 、 potassium iodide 作用下， 以 甲醇 、 六甲基磷酰三胺 为溶剂， 反应 5.7h， 生成 (+)-methyl 2Z,4E-5-[(1S)-1-hydroxy-3-iodo-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoate
  参考文献：
  名称：

  Synthesis and biological activity of 3′-chloro, -bromo, and -iodoabscisic acids, and biological activity of 3′-fluoro-8′-hydroxyabscisic acid

  摘要：

  (+)-3'-氯、-溴和-碘脱落酸被合成，并对其生物学活性和代谢进行了研究，同时也研究了(+)-3'-氟脱落酸的这些性质。这是为了评估脱落酸分子中C-2'位置电子密度变化对其生物学活性和代谢稳定性的影响。在四种生物测定中，(+)-3'-氯、-溴脱落酸的生物活性与(+)-脱落酸相当，或高于后者；而(+)-3'-碘脱落酸在两种生物测定中表现出更强的活性，在另外两种测定中则活性较低。3'-卤代脱落酸的生物活性似乎取决于3'位的卤素，而不是C-2'位的电子密度。在水稻细胞悬浮培养液中，(+)-3'-卤代脱落酸的代谢程度（约降至原浓度的50%）与(+)-脱落酸相似。来自(+)-3'-氯、-溴和-碘脱落酸的代谢产物未在培养液和细胞中检出，而(+)-3'-氟脱落酸产生(+)-3'-氟-8'-羟基脱落酸作为一种稳定的代谢产物。(+)-3'-氟-8'-羟基脱落酸的生物活性低于(+)-3'-氟脱落酸，但高于(-)-3'α-氟法尼酸。这些结果表明，(+)-8'-羟基脱落酸的生物活性介于(+)-脱落酸和(-)-法尼酸之间。脱落酸可能通过植物代谢以逐步的方式被失活。© 1999 Elsevier Science Ltd. 保留所有权利。

  DOI：

  10.1016/s0031-9422(99)00444-6
• 作为产物：
  描述：

  (+)-脱落酸 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以54%的产率得到(+)-2',3'-dihydro-2'α,3'α-epoxyabscisic acid
  参考文献：
  名称：

  （S）-（+）-3'-氟脱落酸的合成，生物活性和代谢

  摘要：

  合成（S）-（+）-3'-氟脱落酸（5a）作为脱落酸的类似物，其由于在C-2'处电子密度增加而可抵抗8'-羟基脱落酸代谢成环酸的代谢环化。5a对莴苣种子萌发的抑制活性略高于脱落酸，与水稻幼苗伸长过程中的脱落酸几乎相等。当将5a施用到豆芽上时，3'-氟-8'-羟基脱落酸（8a），3'α-和3'β-氟代磷酸（9a和10a）以及3'α-和3'β-氟代二氢磷酸（11a和12a）被鉴定为游离代谢产物。甲酯8b，9b和10b以7：6：1的比例平衡存在。该结果表明，随着9a和10a的反向异构化的发生，8a是稳定的。

  DOI：

  10.1016/0040-4020(95)00340-e

文献信息

• Synthesis and photophysical properties of fluorophore-labeled abscisic acid
  作者：X Hou、S R Abrams、J J Balsevich、N Irvine、T Norstrom、M Sikorski、H K Sinha、R P Steer

  DOI：10.1139/v00-087

  日期：2000.7.1

  The 8'-benzophenone, 8'-dansylhydrazone, 3'-S-(2-ethyldansylamide), and 3'-S-acetamidofluorescein derivatives of the plant hormone abscisic acid (ABA) have been synthesized for use in photoaffinity labeling (the benzophenone derivative) or fluorescence probe experiments and have been spectroscopically characterized. One of the three fluorescent compounds, the 3'-tethered fluorescein derivative, exhibits spectroscopic and photophysical properties which indicate that it could be an excellent fluorescent probe of ABA interactions in vivo. The 3'-tethered fluorescein and ABA moieties do not interact strongly, so that the fluorescence properties of the fluorescein-labelled hormone are very similar to those of fluorescein itself. Measurements of the absorption, emission, and fluorescence excitation spectra, fluorescence quantum yields, and fluorescence decay parameters of this derivative as a function of pH indicate that the photophysics is dominated by ground and excited state prototropic equilibria involving only the fluorescein moiety. The fluorescein dianion is the only significant absorber and emitter at pH > 6.7, whereas only the cation absorbs and emits at pH < 0. In the intervening pH range, strong emission from the monoanion and weak emission from two neutral species, tentatively assigned to the zwitterion and the lactone of the fluorescein moiety, is observed.Key words: abscisic acid, fluorescein, synthesis, photophysics.

  植物激素脱落酸（ABA）的8'-苯甲酮、8'-丹磺酰腙、3'-S-(2-乙基丹磺酰胺)和3'-S-乙酰氨基荧光素衍生物已经合成，用于光亲和标记（苯甲酮衍生物）或荧光探针实验，并已经进行了光谱表征。这三种荧光化合物中的一种，3'-连接的荧光素衍生物，展示出光谱和光物理性质，表明它可能是体内ABA相互作用的优秀荧光探针。3'-连接的荧光素和ABA基团之间没有强烈相互作用，因此荧光素标记的激素的荧光性质与荧光素本身非常相似。根据pH值的吸收、发射和荧光激发光谱、荧光量子产率和荧光衰减参数的测量结果表明，这种衍生物的光物理性质主要受到涉及仅涉及荧光素基团的基态和激发态质子平衡的支配。在pH > 6.7时，荧光素二阴离子是唯一重要的吸收和发射体，而在pH < 0时，只有阳离子吸收和发射。在介于这两个pH值之间的范围内，从单阴离子的强发射到两种中性物种的弱发射，初步分配给荧光素基团的带电中性物种和内酯，均可观察到。关键词：脱落酸，荧光素，合成，光物理。
• Activity and utility of abscisic acid having a 3′ thioether linker arm
  作者：John J. Balsevich、Gregory G. Bishop、Gary M. Banowetz

  DOI：10.1016/s0031-9422(96)00440-2

  日期：1997.1

  Abscisic acid (ABA) was functionalized at the 3'-position by reaction of its alpha-2',3'-epoxide with 1,4-butanedithiol to afford the corresponding derivative having a six-atom linker arm containing a terminal sulphhydryl group. This derivative was coupled with epoxy activated Sepharose 6B affording a gel containing ca 1.4 mg of (+)-ABA ml(-1). This gel was shown to bind specifically an anti-ABA antibody from hybridoma culture broth, and its binding capacity was determined. The (+)-ABA analogue possessing the thiol linker arm was also derivatized by reaction with a fluorescent derivatizing agent and these compounds were shown to inhibit cress seed germination. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis and biological activity of 3′-chloro, -bromo, and -iodoabscisic acids, and biological activity of 3′-fluoro-8′-hydroxyabscisic acid
  作者：Sho Arai、Yasushi Todoroki、Satomi Ibaraki、Yoshikazu Naoe、Nobuhiro Hirai、Hajime Ohigashi

  DOI：10.1016/s0031-9422(99)00444-6

  日期：1999.12

  (+)-3'-Chloro, -bromo and -iodoabscisic acids were synthesized, and their biological activities and metabolism were examined, as well as that of (+)-3'-fluoroabscisic acid. This was in order to estimate the effects of altered electron density at the C-2' position of abscisic acid on both biological activity and metabolic stability. The biological activities of (+)-3'-chloro acid bromoabscisic acids were similar to, or higher than, those of(+)-abscisic acid in four bioassays, while (+)-3'-iodoabscisic acid was more potent in two bioassays and less potent than (+)-abscisic acid in the other two bioassays. The biological activities of 3'-haloabscisic acids seem to be dependent on the 3'-halogens, but not on the electron density at C-2'. The metabolism of(+)3'-haloabscisic acids to ca. 50% of their original levels in the media of rice cell suspension culture was similar to that of(+)abscisic acid. Metabolites from (+)-3'-chloro, -bromo and -iodoabscisic acids were not found in the culture media and cells, while (+)-3'-fluoroabscisic acid gave (+)-3'-fluoro-8'-hydroxyabscisic acid as a stable metabolite. (+)-3'-fluoro-8'- hydroxyabscisic acid showed biological activities lower than (+)-3'-fluoroabscisic acid, but higher than (-)-3'alpha-Fluorophascsic acid. These findings suggested that the biological activity of (+)-8'-hydroxyabscisic acid is intermediate between those of (+)abscisic acid and (-)-phaseic acid. Abscisic acid may be inactivated in a stepwise manner by metabolism in plants. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (+)-3'-氯、-溴和-碘脱落酸被合成，并对其生物学活性和代谢进行了研究，同时也研究了(+)-3'-氟脱落酸的这些性质。这是为了评估脱落酸分子中C-2'位置电子密度变化对其生物学活性和代谢稳定性的影响。在四种生物测定中，(+)-3'-氯、-溴脱落酸的生物活性与(+)-脱落酸相当，或高于后者；而(+)-3'-碘脱落酸在两种生物测定中表现出更强的活性，在另外两种测定中则活性较低。3'-卤代脱落酸的生物活性似乎取决于3'位的卤素，而不是C-2'位的电子密度。在水稻细胞悬浮培养液中，(+)-3'-卤代脱落酸的代谢程度（约降至原浓度的50%）与(+)-脱落酸相似。来自(+)-3'-氯、-溴和-碘脱落酸的代谢产物未在培养液和细胞中检出，而(+)-3'-氟脱落酸产生(+)-3'-氟-8'-羟基脱落酸作为一种稳定的代谢产物。(+)-3'-氟-8'-羟基脱落酸的生物活性低于(+)-3'-氟脱落酸，但高于(-)-3'α-氟法尼酸。这些结果表明，(+)-8'-羟基脱落酸的生物活性介于(+)-脱落酸和(-)-法尼酸之间。脱落酸可能通过植物代谢以逐步的方式被失活。© 1999 Elsevier Science Ltd. 保留所有权利。
• Synthesis, biological activity and metabolism of (S)-(+)-3′-Fluoroabscisic acid
  作者：Yasushi Todoroki、Nobuhiro Hirai、Hajime Ohigashi

  DOI：10.1016/0040-4020(95)00340-e

  日期：1995.6

  (S)-(+)-3′-Fluoroabscisic acid (5a) was synthesized as an analogue of abscisic acid that can resist the metabolic cyclization of 8′-hydroxyabscisic acid to phaseic acid due to increased electron density at C-2′. The inhibitory activity of 5a was slightly higher than that of abscisic acid in lettuce seed germination, and was almost equal to that of abscisic acid in rice seedling elongation. When 5a

  合成（S）-（+）-3'-氟脱落酸（5a）作为脱落酸的类似物，其由于在C-2'处电子密度增加而可抵抗8'-羟基脱落酸代谢成环酸的代谢环化。5a对莴苣种子萌发的抑制活性略高于脱落酸，与水稻幼苗伸长过程中的脱落酸几乎相等。当将5a施用到豆芽上时，3'-氟-8'-羟基脱落酸（8a），3'α-和3'β-氟代磷酸（9a和10a）以及3'α-和3'β-氟代二氢磷酸（11a和12a）被鉴定为游离代谢产物。甲酯8b，9b和10b以7：6：1的比例平衡存在。该结果表明，随着9a和10a的反向异构化的发生，8a是稳定的。