Molecular Design and Highly Efficient Synthesis of Molecular Probes Useful for Investigation of Molecular Recognition Mechanisms of Ligand-Receptor Interaction in Gibberellins

用于研究赤霉素配体-受体相互作用的分子识别机制的分子探针的分子设计和高效合成

• 批准号: 09672183
• 负责人: SETO Hideharu
• 金额: $ 1.98万
• 依托单位: The Institute of Physical and Chemical Research (RIKEN)
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 1997
• 资助国家: 日本
• 起止时间: 1997 至 1999
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-09672183/
• 关键词: gibberellin; receptor; photoaffinity-labeling; fluorescein-labeling; α-amylase; synthesis; brassinosteroid; jasmonic acid; three hybrid system; アリューロン細胞

This study intended to design and synthesize gibberellin (GA)-based molecular probes, fluorescein- and photoaffinity-labeled GAs, useful for investigation of molecular recognition mechanisms of ligand-receptor interaction in a phytohormone, GAs. In order to enhance the chemical stability of GA molecule and seek the position suitable for attaching the spacer-functional site, a variety of GA analogs were synthesized from gibberellic acid (GAィイD23ィエD2), and their biological activities were evaluated by α-amylase induction test using half cut barley seeds. On the basis of these data on the structure-activity relationships, fluorescein- and photoaffinity-labeled GAs were respectively assembled via 17-hydroxy-16β, 17-dihydro-19-deoxoGAィイD21ィエD2 derivative.An experiment on the interaction between the fluorescein-labeled GA with a pyrene moiety as the functional site and protoplasts isolated from the barley aleurone layers suggested that GA receptors might be located at the external face of the aleurone plasma membrane. The photoaffinity-labeled GA with aryl diazirine moiety as the functional site is expected to be used for isolation and identification of GA-binding proteins including GA-receptors.To apply the same synthetic strategies to assembling brassinosteroid (BR)- and jasmonic acid (JA)-based molecular probes, the synthetic modification of BR and JA were also carried out to accumulate the data concerning their structure-activity relationships. During the studies, deuterated-, 5-epi-, 6a-carba- and extra-hydroxylated-brassinolides were synthesized. In addition, a variety of JA derivatives including JA-dexamethasone hybrid ligand were synthesized.

这项研究旨在设计和综合基于吉布雷素（GA）的分子问题，荧光素和光性标记的气体，可用于在植物激素中的配体增强物相互作用的分子识别机制的投资。为了增强GA分子的化学稳定性并寻求适合连接间隔功能位点的位置，从Gibberellelic Acid（GAII D23E D2）合成了各种GA类似物，并使用半切割Barley Seeds通过α-淀粉酶诱导测试来评估其生物学活性。根据这些有关结构活性关系的数据，分别通过17-羟基-16β，17-Dihydro-19-二氧基-19-脱氧oxogaii d21ie d2衍生物分别组装荧光素和光，荧光素和光的气体。建议GA受体可能位于核龙质膜的外表面。 The photoaffinity-labeled GA with aryl diazirine moiety as the functional site is expected to be used for isolation and identification of GA-binding proteins including GA-receptors.To apply the same synthetic strategies to assembling brassinosteroid (BR)- and jasmonic acid (JA)-based molecular problems, the synthetic modification of BR and JA were also carried out to accumulate the data concerning their structure-activity relationships.在研究过程中，合成了氘代，5-EPI-，6A-CARBA和羟基化的黄质醇。此外，合成了多种JA衍生物，包括Ja--------杂种配体。

项目成果

Hideharu Seto: "2,3,5-Tri-epi-brassinolide : Preparation And Biological Activity in Rice Lamina Inclination Test"Phytochemistry. 52(5). 815-818 (1999)

Hideharu Seto：“2,3,5-Tri-epi-brassinolide：制备及其在水稻叶片倾斜试验中的生物活性”植物化学。

Hideharu Seto: "Reactivities of Gibberellins with a Cationic Exchange Resin, Dowex-50W"Heterocycles. 52(2)(in press). (2000)

Hideharu Seto：“赤霉素与阳离子交换树脂，Dowex-50W 的反应性”杂环。

H.Seto, S.Fujioka, H.Koshino, T.Suenaga, S.Yoshida, T.Watanabe and S.Takatsuto: "Epimerization at C-5 of Brassinolide with Sodium Methoxide and the Biological Activity of 5-epi-Brassinolide in the Rice Lamina Inclination Test"J. Chem. Soc., Perkin Trans.1

H.Seto、S.Fujioka、H.Koshino、T.Suenaga、S.Yoshida、T.Watanabe 和 S.Takatsuto：“油菜素内酯在 C-5 处与甲醇钠的差向异构化以及 5-表位油菜素内酯的生物活性

H.Seto, S.Fujioka, H.Koshino, T.Suenaga, S.Yoshida, T.Watanabe and S.Takatsuto: "2,3,5-Tri-epi-brassinolide: Preparation And Biological Activity in Rice Lamina Inclination Test"Phytochemistry. 52 (5). 815-818 (1999)

H.Seto、S.Fujioka、H.Koshino、T.Suenaga、S.Yoshida、T.Watanabe 和 S.Takatsuto：“2,3,5-Tri-epi-brassinolide：水稻叶片倾斜试验中的制备和生物活性

Hideharu Seto: "A General Approach to Synthesis of Labeled Brassinosteroids:Preparation of [25,26,27-^2H_7]Brassinolide with 60% Isotopic Purity from the Parent Brassinolide." Tetrahedron Lett.39(41). 7525-7528 (1998)

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