ChemBioChem published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Application of (E)-3-(3-Nitrophenyl)acrylic acid.
McInnis, Christine E. published the artcileNon-native N-Aroyl L-Homoserine Lactones Are Potent Modulators of the Quorum Sensing Receptor RpaR in Rhodopseudomonas palustris, Application of (E)-3-(3-Nitrophenyl)acrylic acid, the publication is ChemBioChem (2014), 15(1), 87-93, database is CAplus and MEDLINE.
Quorum sensing (QS) is a process by which bacteria use low-mol.-weight signaling mols. (or autoinducers) to assess their local population densities and alter gene expression levels at high cell numbers Many Gram-neg. bacteria use N-acyl L-homoserine lactones (AHLs) with aliphatic acyl groups as signaling mols. for QS. However, bacteria that use AHLs with aroyl acyl groups have been recently discovered; they include the metabolically versatile soil bacterium Rhodopseudomonas palustris, which uses p-coumaroyl HL (p-cAHL) as its QS signal. This autoinducer is especially unusual because its acyl group is believed to originate from a monolignol (i.e., p-coumarate) produced exogenously by plants in the R. palustris environment, rather than through the endogenous fatty acid biosynthesis pathway like other native AHLs. As such, p-cAHL could signal not only bacterial d., but also the availability of an exogenous plant-derived substrate and might even constitute an interkingdom signal. Like other Gram-neg. bacteria, QS in R. palustris is controlled by the p-cAHL signal binding its cognate LuxR-type receptor, RpaR. The authors sought to determine if non-native aroyl HLs (ArHLs) could potentially activate or inhibit RpaR in R. palustris, and thereby modulate QS in this bacterium. Herein, the authors report the testing of a set of synthetic ArHLs for RpaR agonism and antagonism by using a R. palustris reporter strain. Several potent non-native RpaR agonists and antagonists were identified. Addnl., the screening data revealed that lower concentrations of ArHL are required to strongly agonize RpaR than to antagonize it. Structure-activity relation analyses of the active ArHLs indicated that potent RpaR agonists tend to have sterically small substituents on their aryl groups, most notably in the ortho position. In turn, the most potent RpaR antagonists were based on either the phenylpropionyl HL (PPHL) or the phenoxyacetyl HL (POHL) scaffold, and many contained an electron-withdrawing group at either the meta or para positions of the aryl ring. To the authors’ knowledge, the compounds reported herein represent the first abiotic chem. modulators of RpaR, and more generally, the first abiotic ligands capable of intercepting QS in bacteria that use native ArHL signals. In view of the origins of the p-cAHL signal in R. palustris, the largely unknown role of QS in this bacterium, and R. palustris’ unique environmental lifestyles, the authors anticipate that these compounds could be valuable as chem. probes to study QS in R. palustris in a range of fundamental and applied contexts.
ChemBioChem published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Application of (E)-3-(3-Nitrophenyl)acrylic acid.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia