2-difluoromethylene-4-methylenepentanoic acid, a paradoxical probe able to mimic the signaling role of 2-oxoglutaric acid in cyanobacteria.

Xinjun Liu, Han Chen, Erik Laurini, Yang Wang, Valentina Dal Col, Paola Posocco, Fabio Ziarelli, Maurizio Fermeglia, Cheng-Cai Zhang, Sabrina Pricl, Ling Peng

College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, PR China.

Organic letters 2011 Jun 3

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2-Difluoromethylene-4-methylenepentanoic acid (DFMPA), a seemingly deviated analog of 2-oxoglutaric acid (2-OG), could surprisingly mimic its signaling function in cyanobacteria. Computer modeling revealed the favorable binding of DFMPA toward the 2-OG receptor, NtcA, via mutual conformational changes, suggesting that structural alteration of 2-OG is tolerated for it to exercise its signaling role. This extremely useful finding could be exploited for the design of affinity probes with which to study new 2-OG receptors in related signaling pathways.

Citation

Xinjun Liu, Han Chen, Erik Laurini, Yang Wang, Valentina Dal Col, Paola Posocco, Fabio Ziarelli, Maurizio Fermeglia, Cheng-Cai Zhang, Sabrina Pricl, Ling Peng. 2-difluoromethylene-4-methylenepentanoic acid, a paradoxical probe able to mimic the signaling role of 2-oxoglutaric acid in cyanobacteria. Organic letters. 2011 Jun 3;13(11):2924-7