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

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 m...

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Autores principales: Kang, Sun-Young, Lee, Jae Kyoung, Jang, Jae-Hyuk, Hwang, Bang Yeon, Hong, Young-Soo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: BioMed Central 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4659178/
https://www.ncbi.nlm.nih.gov/pubmed/26608135
http://dx.doi.org/10.1186/s12934-015-0379-1
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author Kang, Sun-Young
Lee, Jae Kyoung
Jang, Jae-Hyuk
Hwang, Bang Yeon
Hong, Young-Soo
author_facet Kang, Sun-Young
Lee, Jae Kyoung
Jang, Jae-Hyuk
Hwang, Bang Yeon
Hong, Young-Soo
author_sort Kang, Sun-Young
collection PubMed
description 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 ± 1.0 mg/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. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s12934-015-0379-1) contains supplementary material, which is available to authorized users.
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spelling pubmed-46591782015-11-26 Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli Kang, Sun-Young Lee, Jae Kyoung Jang, Jae-Hyuk Hwang, Bang Yeon Hong, Young-Soo Microb Cell Fact Research 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 ± 1.0 mg/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. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s12934-015-0379-1) contains supplementary material, which is available to authorized users. BioMed Central 2015-11-25 /pmc/articles/PMC4659178/ /pubmed/26608135 http://dx.doi.org/10.1186/s12934-015-0379-1 Text en © Kang et al. 2015 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research
Kang, Sun-Young
Lee, Jae Kyoung
Jang, Jae-Hyuk
Hwang, Bang Yeon
Hong, Young-Soo
Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli
title Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli
title_full Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli
title_fullStr Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli
title_full_unstemmed Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli
title_short Production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in Escherichia coli
title_sort production of phenylacetyl-homoserine lactone analogs by artificial biosynthetic pathway in escherichia coli
topic Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4659178/
https://www.ncbi.nlm.nih.gov/pubmed/26608135
http://dx.doi.org/10.1186/s12934-015-0379-1
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