Design and synthesis of biotin-tagged photoaffinity probes of jasmonates

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• 作者：Min Gu ; Jianbin Yan ; Zhiyan Bai ; Yue-Ting Chen ; Wei Lu ; Jie Tang ; Liusheng Duan ; Daoxin Xie ; Fa-Jun Nan
• 关键词：Jasmonate ; Coronatine ; Photoaffinity probes ; Synthesis
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2010
• 出版时间：1 May 2010
• 年：2010
• 卷：18
• 期：9
• 页码：3012-3019
• 全文大小：698 K

文摘

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.