Design and synthesis of biotin-tagged photoaffinity probes of jasmonates

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

Design and synthesis of biotin-tagged photoaffinity probes of jasmonates

Min Gu
, Jianbin Yan
, Zhiyan Bai
, Yue Ting Chen
, Wei Lu
, Jie Tang
, Liusheng Duan
, Daoxin Xie^*
, Fa Jun Nan

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University
CAS - Shanghai Institute of Materia Medica
Tsinghua University

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	3012-3019
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	9
DOIs	https://doi.org/10.1016/j.bmc.2010.03.059
State	Published - 1 May 2010

Keywords

Coronatine
Jasmonate
Photoaffinity probes
Synthesis

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10.1016/j.bmc.2010.03.059

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@article{a0321d1950d24530b567f5dd5bebafdd,

title = "Design and synthesis of biotin-tagged photoaffinity probes of jasmonates",

abstract = "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.",

keywords = "Coronatine, Jasmonate, Photoaffinity probes, Synthesis",

author = "Min Gu and Jianbin Yan and Zhiyan Bai and Chen, \{Yue Ting\} and Wei Lu and Jie Tang and Liusheng Duan and Daoxin Xie and Nan, \{Fa Jun\}",

year = "2010",

month = may,

day = "1",

doi = "10.1016/j.bmc.2010.03.059",

language = "英语",

volume = "18",

pages = "3012--3019",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

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TY - JOUR

T1 - Design and synthesis of biotin-tagged photoaffinity probes of jasmonates

AU - Gu, Min

AU - Yan, Jianbin

AU - Bai, Zhiyan

AU - Chen, Yue Ting

AU - Lu, Wei

AU - Tang, Jie

AU - Duan, Liusheng

AU - Xie, Daoxin

AU - Nan, Fa Jun

PY - 2010/5/1

Y1 - 2010/5/1

N2 - 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.

AB - 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.

KW - Coronatine

KW - Jasmonate

KW - Photoaffinity probes

KW - Synthesis

UR - https://www.scopus.com/pages/publications/77951297442

U2 - 10.1016/j.bmc.2010.03.059

DO - 10.1016/j.bmc.2010.03.059

M3 - 文章

C2 - 20395151

AN - SCOPUS:77951297442

SN - 0968-0896

VL - 18

SP - 3012

EP - 3019

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 9

ER -

Design and synthesis of biotin-tagged photoaffinity probes of jasmonates

Abstract

Keywords

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