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

doi:10.1021/ol2009544

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

Org Lett. 2011 Jun 3;13(11):2924-7. doi: 10.1021/ol2009544. Epub 2011 May 5.

Authors

Xinjun Liu¹, Han Chen, Erik Laurini, Yang Wang, Valentina Dal Col, Paola Posocco, Fabio Ziarelli, Maurizio Fermeglia, Cheng-Cai Zhang, Sabrina Pricl, Ling Peng

Affiliation

¹ College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, PR China.

PMID: 21545161
DOI: 10.1021/ol2009544

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyanobacteria / metabolism*
Ketoglutaric Acids / chemistry
Ketoglutaric Acids / metabolism*
Molecular Structure
Pentanoic Acids / chemistry
Pentanoic Acids / metabolism*
Signal Transduction

Substances

2-difluoromethylene-4-methylenepentanoic acid
Ketoglutaric Acids
Pentanoic Acids