Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli

Sun Young Kang, Jae Kyoung Lee, Jae Hyuk Jang, Bang Yeon Hwang, Young Soo Hong

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


Background: Quorum sensing (QS) networks are more commonly known as acyl homoserine lactone (HSL) networks. Recently, p-coumaroyl-HSL has been found in a photosynthetic bacterium. p-coumaroyl-HSL is derived from a lignin monomer, p-coumaric acid, rather than a fatty acyl group. The p-coumaroyl-HSL may serve an ecological role in diverse QS pathways between p-coumaroyl-HSL producing bacteria and specific plants. Interference with QS has been regarded as a novel way to control bacterial infections. Heterologous production of the QS molecule, p-coumaroyl-HSL, could provide a sustainable and controlled means for its large-scale production, in contrast to the restricted feedback regulation and extremely low productivity of natural producers. Results: We developed an artificial biosynthetic process for phenylacetyl-homoserine lactone analogs, including cinnamoyl-HSL, p-coumaroyl-HSL, caffeoyl-HSL, and feruloyl-HSL, using a bioconversion method via E. coli (CB1) in the co-expression of the codon-optimized LuxI-type synthase (RpaI) and p-coumaroyl-CoA ligase (4CL2nt). In addition to this, we show the de novo production of p-coumaroyl-HSL in heterologous host E. coli (DN1) and tyrosine overproducing E. coli (DN2), containing the rpaI gene in addition to p-coumaroyl-CoA biosynthetic genes. The yields for p-coumaroyl-HSL reached 93.4±0.6 and 142.5±1.0mg/L in the S-adenosyl-l-methionine and l-methionine feeding culture in the DN2 strain, respectively. Conclusions: This is the first report of a de novo biosynthesis in a heterologous host yielding a QS molecule, p-coumaroyl-HSL from a glucose medium using a single vector system combining p-coumaroyl-CoA biosynthetic genes and the LuxI-type synthase gene.

Original languageEnglish (US)
Article number191
JournalMicrobial Cell Factories
Issue number1
StatePublished - Nov 25 2015
Externally publishedYes

Bibliographical note

Funding Information:
This work was supported in part by Global R&D Center program (NRF‑ 2010‑00719), NRF and by the Next‑Generation BioGreen 21 Program (SSAC, PJ011084012015), RDA Republic of Korea. We thank the Gyeonggi Bio Center for the HRESIMS data and the KBSI, Ochang, for the NMR data.

Publisher Copyright:
© 2015 Kang et al.


  • Artificial biosynthesis
  • Homoserine lactone (HSL)
  • Phenylacetyl-HSL
  • p-coumaroyl-HSL


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