2-PENTEN-4-YNOIC ACID, 5-(TRIMETHYLSILYL)-, ETHYL ESTER, (Z)-

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CAS: 54599-62-1
MF: C10H16O2Si
MW: 196.31834
Synonyms: 2-PENTEN-4-YNOIC ACID, 5-(TRIMETHYLSILYL)-, ETHYL ESTER, (Z)-

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Zhaohai Qin

China Agricultural University
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Co-reporter: Liu Wenjian, Han Xiaoqiang, Xiao Yumei, Fan Jinlong, Zhang Yuanzhi, Lu Huizhe, Wang Mingan, Qin Zhaohai
pp: 72-80
Publication Date(Web):December 2013
DOI: 10.1016/j.phytochem.2013.09.029
•A cis-2,3-cyclopropanated ABA analogue was designed and synthesized successfully.•Its photostability is 4-fold higher than that of (±)-ABA.•cis-2,3-cyclopropanated ABA has high ABA-like activity.The plant hormone abscisic acid (ABA) plays a central role in the regulation of plant development and adaptation to environmental stress. The isomerization of ABA to the biologically inactive 2E-isomer by light considerably limits its applications in agricultural fields. To overcome this shortcoming, an ABA analogue, cis-2,3-cyclopropanated ABA, was synthesized, and its photostability and biological activities were investigated. This compound showed high photostability under UV light exposure, which was 4-fold higher than that of (±)-ABA. cis-2,3-cyclopropanated ABA exhibited high ABA-like activity, including the ability to effectively inhibit seed germination, seedling growth and stomatal movements of Arabidopsis. In some cases, its bioactivity approaches that of (±)-ABA. trans-2,3-cyclopropanated abscisic acid was also prepared, an isomer that was more photostable but which showed weak ABA-like activity.To inhibit the isomerization of plant hormone ABA by light, a cis-2,3-cyclopropanated ABA analogue was designed and synthesized successfully. The compound has notably higher photostability compared to ABA and shows high ABA-like activity.Image for unlabelled figure

HuiZhe Lu

China Agricultural University
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Ming-An Wang

China Agricultural University
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