An N-acyl-L-homoserine lactone having 4-coumaroyl as the acyl substituent.

Identification

IUPAC Names

3-(4-hydroxyphenyl)-N-[(3S)-2-oxotetrahydrofuran-3-yl]prop-2-enamide

Molecular Formula
C13H13NO4
Mass
247.24660
Monoisotopic Mass
247.08446
Charge
0
InChI
InChI=1S/C13H13NO4/c15-10-4-1-9(2-5-10)3-6-12(16)14-11-7-8-18-13(11)17/h1-6,11,15H,7-8H2,(H,14,16)/t11-/m0/s1
InChIKey
CCIXZFJYFQJTGK-NSHDSACASA-N
SMILES
Oc1ccc(C=CC(=O)N[C@H]2CCOC2=O)cc1
Synonyms

3-(4-hydroxyphenyl)-N-[(3S)-2-oxotetrahydrofuran-3-yl]acrylamide

N-(4-coumaroyl)-L-homoserine lactone

N-(p-coumaroyl)-L-homoserine lactone

Species

Europe PubMed Central results


A new class of homoserine lactone quorum-sensing signals.

Author: Schaefer AL, Greenberg EP, Oliver CM, Oda Y, Huang JJ, Bittan-Banin G, Peres CM, Schmidt S, Juhaszova K, Sufrin JR, Harwood CS.

Abstract: Quorum sensing is a term used to describe cell-to-cell communication that allows cell-density-dependent gene expression. Many bacteria use acyl-homoserine lactone (acyl-HSL) synthases to generate fatty acyl-HSL quorum-sensing signals, which function with signal receptors to control expression of specific genes. The fatty acyl group is derived from fatty acid biosynthesis and provides signal specificity, but the variety of signals is limited. Here we show that the photosynthetic bacterium Rhodopseudomonas palustris uses an acyl-HSL synthase to produce p-coumaroyl-HSL by using environmental p-coumaric acid rather than fatty acids from cellular pools. The bacterium has a signal receptor with homology to fatty acyl-HSL receptors that responds to p-coumaroyl-HSL to regulate global gene expression. We also found that p-coumaroyl-HSL is made by other bacteria including Bradyrhizobium sp. and Silicibacter pomeroyi. This discovery extends the range of possibilities for acyl-HSL quorum sensing and raises fundamental questions about quorum sensing within the context of environmental signalling.