Studying the signaling role of 2-oxoglutaric acid using analogs that mimic the ketone and ketal forms of 2-oxoglutaric acid

被引:21
作者
Chen, Han
Laurent, Sophie
Bedu, Sylvie
Ziarelli, Fabio
Chen, Hai-li
Cheng, Yong
Zhang, Cheng-Cai
Peng, Ling [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
[2] CNRS, Inst Biol Struct & Microbiol, Chim Bacterienne Lab, F-13402 Marseille 20, France
[3] Univ Aix Marseille 1, Fac Sci & Tech St Jerome, F-13397 Marseille 13, France
[4] Univ Aix Marseille 3, Fac Sci & Tech St Jerome, F-13397 Marseille 13, France
[5] CNRS, Dept Chim, UMR 6114, F-13288 Marseille 09, France
[6] Huazhong Agr Univ, Natl Key Lab Agr Microbiol, Wuhan 430070, Peoples R China
来源
CHEMISTRY & BIOLOGY | 2006年 / 13卷 / 08期
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.chembiol.2006.06.009
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
2-Oxoglutaric acid (2-OG), a Krebs cycle intermediate, is a signaling molecule in many organisms. To determine which form of 2-OG, the ketone or the ketal form, is responsible for its signaling function, we have synthesized and characterized various 2-OG analogs. Only 2-methylenepentanedioic acid (2-MPA), which resembles closely the ketone form of 2-OG, is able to elicit cell responses in the cyanobacterium Anabaena by inducing nitrogen-fixing cells called heterocysts. None of the analogs mimicking the ketal form of 2-OG are able to induce heterocysts because none of them are able to interact with NtcA, a 2-OG sensor. NtcA interacts with 2-MPA and 2-OG in a similar manner, and it is necessary for heterocyst differentiation induced by 2-MPA. Therefore, it is primarily the ketone form that is responsible for the signaling role of 2-OG in Anabaena.
引用
收藏
页码:849 / 856
页数:8
相关论文
共 35 条
[1]   A SHORT LARGE-SCALE SYNTHESIS OF (+/-)SARKOMYCIN ESTERS [J].
AMRI, H ;
RAMBAUD, M ;
VILLIERAS, J .
TETRAHEDRON LETTERS, 1989, 30 (52) :7381-7382
[2]   TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE [J].
APPEL, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12) :801-811
[3]  
BAILEY J, 1982, J BIOL CHEM, V257, P5579
[4]   Expression of the Anabaena hetR gene from a copper-regulated promoter leads to heterocyst differentiation under repressing conditions [J].
Buikema, WJ ;
Haselkorn, R .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (05) :2729-2734
[5]  
Chen HW, 2001, ANGEW CHEM INT EDIT, V40, P607, DOI 10.1002/1521-3773(20010202)40:3<607::AID-ANIE607>3.0.CO
[6]  
2-8
[7]  
CHENG XZ, 1996, J CHEM SOC P1, P1741
[8]  
CRISTINA P, 2004, CHEMBIOCHEM, V5, P590
[9]   SYNTHESIS OF 2-HYDROXY-3-METHYL-2-CYCLOPENTENONE, CORYLONE, FROM 2-KETOGLUTARIC ACID [J].
DOSSANTOS, ML ;
DEMAGALHAES, GC .
SYNTHETIC COMMUNICATIONS, 1991, 21 (17) :1783-1788
[10]  
EZQUERRA J, 1994, TETRAHEDRON-ASYMMETR, V5, P921