Three steps in one pot: biosynthesis of 4-hydroxycinnamyl alcohols using immobilized whole cells of two genetically engineered Escherichia coli strains.
Identifieur interne : 001149 ( Main/Exploration ); précédent : 001148; suivant : 001150Three steps in one pot: biosynthesis of 4-hydroxycinnamyl alcohols using immobilized whole cells of two genetically engineered Escherichia coli strains.
Auteurs : Shuxin Liu [République populaire de Chine] ; Jiabin Liu [République populaire de Chine] ; Jiayin Hou [République populaire de Chine] ; Nan Chao [République populaire de Chine] ; Ying Gai [République populaire de Chine] ; Xiangning Jiang [République populaire de Chine]Source :
- Microbial cell factories [ 1475-2859 ] ; 2017.
Descripteurs français
- KwdFr :
- Alcohol oxidoreductases (métabolisme), Cellules immobilisées (métabolisme), Escherichia coli (cytologie), Escherichia coli (génétique), Escherichia coli (métabolisme), Génie génétique (MeSH), Propanols (composition chimique), Propanols (métabolisme), Protéines recombinantes (métabolisme), Voies de biosynthèse (MeSH).
- MESH :
- composition chimique : Propanols.
- cytologie : Escherichia coli.
- génétique : Escherichia coli.
- métabolisme : Alcohol oxidoreductases, Cellules immobilisées, Escherichia coli, Propanols, Protéines recombinantes.
- Génie génétique, Voies de biosynthèse.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Propanols.
- chemical , metabolism : Alcohol Oxidoreductases, Propanols, Recombinant Proteins.
- cytology : Escherichia coli.
- genetics : Escherichia coli.
- metabolism : Cells, Immobilized, Escherichia coli.
- Biosynthetic Pathways, Genetic Engineering.
Abstract
BACKGROUND
4-Hydroxycinnamyl alcohols are a class of natural plant secondary metabolites that include p-coumaryl alcohol, caffeyl alcohol, coniferyl alcohol and sinapyl alcohol, and have physiological, ecological and biomedical significance. While it is necessary to investigate the biological pathways and economic value of these alcohols, research is hindered because of their limited availability and high cost. Traditionally, these alcohols are obtained by chemical synthesis and plant extraction. However, synthesis by biotransformation with immobilized microorganisms is of great interest because it is environmentally friendly and offers high stability and regenerable cofactors. Therefore, we produced 4-hydroxycinnamyl alcohols using immobilized whole cells of engineered Escherichia coli as the biocatalyst.
RESULTS
In this study, we used the recombinant E. coli strain, M15-4CL1-CCR, expressing the fusion protein 4-coumaric acid: coenzyme A ligase and the cinnamoyl coenzyme A reductase and a recombinant E. coli strain, M15-CAD, expressing cinnamyl alcohol dehydrogenase from Populus tomentosa (P. tomentosa). High performance liquid chromatography and mass spectrometry showed that the immobilized whole cells of the two recombinant E. coli strains could effectively convert the phenylpropanoic acids to their corresponding 4-hydroxycinnamyl alcohols. Further, the optimum buffer pH and the reaction temperature were pH 7.0 and 30 °C. Under these conditions, the molar yield of the p-coumaryl alcohol, the caffeyl alcohol and the coniferyl alcohol was around 58, 24 and 60%, respectively. Moreover, the highly sensitive and selective HPLC-PDA-ESI-MSn method used in this study could be applied to the identification and quantification of these aromatic polymers.
CONCLUSIONS
We have developed a dual-cell immobilization system for the production of 4-hydroxycinnamyl alcohols from inexpensive phenylpropanoic acids. This biotransformation method is both simple and environmental-friendly, which is promising for the practical and cost effective synthesis of natural products. Graphical abstract Biotransformation process of phenylpropanoic acids by immobilized whole-cells.
DOI: 10.1186/s12934-017-0722-9
PubMed: 28606145
PubMed Central: PMC5468945
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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Chine</country><wicri:regionArea>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation></author><author><name sortKey="Liu, Jiabin" sort="Liu, Jiabin" uniqKey="Liu J" first="Jiabin" last="Liu">Jiabin Liu</name><affiliation wicri:level="1"><nlm:affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation></author><author><name sortKey="Hou, Jiayin" sort="Hou, Jiayin" uniqKey="Hou J" first="Jiayin" last="Hou">Jiayin Hou</name><affiliation wicri:level="1"><nlm:affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation></author><author><name sortKey="Chao, Nan" sort="Chao, Nan" uniqKey="Chao N" first="Nan" last="Chao">Nan Chao</name><affiliation wicri:level="1"><nlm:affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation></author><author><name sortKey="Gai, Ying" sort="Gai, Ying" uniqKey="Gai Y" first="Ying" last="Gai">Ying Gai</name><affiliation wicri:level="1"><nlm:affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:affiliation>The Tree and Ornamental Plant Breeding and Biotechnology Laboratory of Chinese Forestry Administration, National Engineering Laboratory for Tree Breeding, Beijing, 100083, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>The Tree and Ornamental Plant Breeding and Biotechnology Laboratory of Chinese Forestry Administration, National Engineering Laboratory for Tree Breeding, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation></author><author><name sortKey="Jiang, Xiangning" sort="Jiang, Xiangning" uniqKey="Jiang X" first="Xiangning" last="Jiang">Xiangning Jiang</name><affiliation wicri:level="1"><nlm:affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China. jiangxn@bjfu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:affiliation>The Tree and Ornamental Plant Breeding and Biotechnology Laboratory of Chinese Forestry Administration, National Engineering Laboratory for Tree Breeding, Beijing, 100083, People's Republic of China. jiangxn@bjfu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>The Tree and Ornamental Plant Breeding and Biotechnology Laboratory of Chinese Forestry Administration, National Engineering Laboratory for Tree Breeding, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation></author></analytic><series><title level="j">Microbial cell factories</title><idno type="eISSN">1475-2859</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alcohol Oxidoreductases (metabolism)</term><term>Biosynthetic Pathways (MeSH)</term><term>Cells, Immobilized (metabolism)</term><term>Escherichia coli (cytology)</term><term>Escherichia coli (genetics)</term><term>Escherichia coli (metabolism)</term><term>Genetic Engineering (MeSH)</term><term>Propanols (chemistry)</term><term>Propanols (metabolism)</term><term>Recombinant Proteins (metabolism)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Alcohol oxidoreductases (métabolisme)</term><term>Cellules immobilisées (métabolisme)</term><term>Escherichia coli (cytologie)</term><term>Escherichia coli (génétique)</term><term>Escherichia coli (métabolisme)</term><term>Génie génétique (MeSH)</term><term>Propanols (composition chimique)</term><term>Propanols (métabolisme)</term><term>Protéines recombinantes (métabolisme)</term><term>Voies de biosynthèse (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Propanols</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Alcohol Oxidoreductases</term><term>Propanols</term><term>Recombinant Proteins</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Propanols</term></keywords><keywords scheme="MESH" qualifier="cytologie" xml:lang="fr"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="cytology" xml:lang="en"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Cells, Immobilized</term><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Alcohol oxidoreductases</term><term>Cellules immobilisées</term><term>Escherichia coli</term><term>Propanols</term><term>Protéines recombinantes</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Biosynthetic Pathways</term><term>Genetic Engineering</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Génie génétique</term><term>Voies de biosynthèse</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p><b>BACKGROUND</b></p><p>4-Hydroxycinnamyl alcohols are a class of natural plant secondary metabolites that include p-coumaryl alcohol, caffeyl alcohol, coniferyl alcohol and sinapyl alcohol, and have physiological, ecological and biomedical significance. While it is necessary to investigate the biological pathways and economic value of these alcohols, research is hindered because of their limited availability and high cost. Traditionally, these alcohols are obtained by chemical synthesis and plant extraction. However, synthesis by biotransformation with immobilized microorganisms is of great interest because it is environmentally friendly and offers high stability and regenerable cofactors. Therefore, we produced 4-hydroxycinnamyl alcohols using immobilized whole cells of engineered Escherichia coli as the biocatalyst.</p></div><div type="abstract" xml:lang="en"><p><b>RESULTS</b></p><p>In this study, we used the recombinant E. coli strain, M15-4CL1-CCR, expressing the fusion protein 4-coumaric acid: coenzyme A ligase and the cinnamoyl coenzyme A reductase and a recombinant E. coli strain, M15-CAD, expressing cinnamyl alcohol dehydrogenase from Populus tomentosa (P. tomentosa). High performance liquid chromatography and mass spectrometry showed that the immobilized whole cells of the two recombinant E. coli strains could effectively convert the phenylpropanoic acids to their corresponding 4-hydroxycinnamyl alcohols. Further, the optimum buffer pH and the reaction temperature were pH 7.0 and 30 °C. Under these conditions, the molar yield of the p-coumaryl alcohol, the caffeyl alcohol and the coniferyl alcohol was around 58, 24 and 60%, respectively. Moreover, the highly sensitive and selective HPLC-PDA-ESI-MSn method used in this study could be applied to the identification and quantification of these aromatic polymers.</p></div><div type="abstract" xml:lang="en"><p><b>CONCLUSIONS</b></p><p>We have developed a dual-cell immobilization system for the production of 4-hydroxycinnamyl alcohols from inexpensive phenylpropanoic acids. This biotransformation method is both simple and environmental-friendly, which is promising for the practical and cost effective synthesis of natural products. Graphical abstract Biotransformation process of phenylpropanoic acids by immobilized whole-cells.</p></div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">28606145</PMID><DateCompleted><Year>2017</Year><Month>11</Month><Day>08</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">1475-2859</ISSN><JournalIssue CitedMedium="Internet"><Volume>16</Volume><Issue>1</Issue><PubDate><Year>2017</Year><Month>Jun</Month><Day>12</Day></PubDate></JournalIssue><Title>Microbial cell factories</Title><ISOAbbreviation>Microb Cell Fact</ISOAbbreviation></Journal><ArticleTitle>Three steps in one pot: biosynthesis of 4-hydroxycinnamyl alcohols using immobilized whole cells of two genetically engineered Escherichia coli strains.</ArticleTitle><Pagination><MedlinePgn>104</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1186/s12934-017-0722-9</ELocationID><Abstract><AbstractText Label="BACKGROUND" NlmCategory="BACKGROUND">4-Hydroxycinnamyl alcohols are a class of natural plant secondary metabolites that include p-coumaryl alcohol, caffeyl alcohol, coniferyl alcohol and sinapyl alcohol, and have physiological, ecological and biomedical significance. While it is necessary to investigate the biological pathways and economic value of these alcohols, research is hindered because of their limited availability and high cost. Traditionally, these alcohols are obtained by chemical synthesis and plant extraction. However, synthesis by biotransformation with immobilized microorganisms is of great interest because it is environmentally friendly and offers high stability and regenerable cofactors. Therefore, we produced 4-hydroxycinnamyl alcohols using immobilized whole cells of engineered Escherichia coli as the biocatalyst.</AbstractText><AbstractText Label="RESULTS" NlmCategory="RESULTS">In this study, we used the recombinant E. coli strain, M15-4CL1-CCR, expressing the fusion protein 4-coumaric acid: coenzyme A ligase and the cinnamoyl coenzyme A reductase and a recombinant E. coli strain, M15-CAD, expressing cinnamyl alcohol dehydrogenase from Populus tomentosa (P. tomentosa). High performance liquid chromatography and mass spectrometry showed that the immobilized whole cells of the two recombinant E. coli strains could effectively convert the phenylpropanoic acids to their corresponding 4-hydroxycinnamyl alcohols. Further, the optimum buffer pH and the reaction temperature were pH 7.0 and 30 °C. Under these conditions, the molar yield of the p-coumaryl alcohol, the caffeyl alcohol and the coniferyl alcohol was around 58, 24 and 60%, respectively. Moreover, the highly sensitive and selective HPLC-PDA-ESI-MSn method used in this study could be applied to the identification and quantification of these aromatic polymers.</AbstractText><AbstractText Label="CONCLUSIONS" NlmCategory="CONCLUSIONS">We have developed a dual-cell immobilization system for the production of 4-hydroxycinnamyl alcohols from inexpensive phenylpropanoic acids. This biotransformation method is both simple and environmental-friendly, which is promising for the practical and cost effective synthesis of natural products. Graphical abstract Biotransformation process of phenylpropanoic acids by immobilized whole-cells.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Shuxin</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Jiabin</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hou</LastName><ForeName>Jiayin</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chao</LastName><ForeName>Nan</ForeName><Initials>N</Initials><AffiliationInfo><Affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Gai</LastName><ForeName>Ying</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>The Tree and Ornamental Plant Breeding and Biotechnology Laboratory of Chinese Forestry Administration, National Engineering Laboratory for Tree Breeding, Beijing, 100083, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Jiang</LastName><ForeName>Xiangning</ForeName><Initials>X</Initials><AffiliationInfo><Affiliation>College of Biological Science and Technology, Beijing Forestry University, Beijing, 100083, People's Republic of China. jiangxn@bjfu.edu.cn.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>The Tree and Ornamental Plant Breeding and Biotechnology Laboratory of Chinese Forestry Administration, National Engineering Laboratory for Tree Breeding, Beijing, 100083, People's Republic of China. jiangxn@bjfu.edu.cn.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2017</Year><Month>06</Month><Day>12</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Microb Cell Fact</MedlineTA><NlmUniqueID>101139812</NlmUniqueID><ISSNLinking>1475-2859</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D020005">Propanols</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011994">Recombinant Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 1.1.-</RegistryNumber><NameOfSubstance UI="D000429">Alcohol Oxidoreductases</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 1.1.1.195</RegistryNumber><NameOfSubstance UI="C018656">cinnamyl alcohol dehydrogenase</NameOfSubstance></Chemical><Chemical><RegistryNumber>SS8YOP444F</RegistryNumber><NameOfSubstance UI="C020722">cinnamyl alcohol</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000429" MajorTopicYN="N">Alcohol Oxidoreductases</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D053898" MajorTopicYN="N">Biosynthetic Pathways</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018914" MajorTopicYN="N">Cells, Immobilized</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004926" MajorTopicYN="N">Escherichia coli</DescriptorName><QualifierName UI="Q000166" MajorTopicYN="N">cytology</QualifierName><QualifierName UI="Q000235" MajorTopicYN="Y">genetics</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005818" MajorTopicYN="Y">Genetic Engineering</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D020005" MajorTopicYN="N">Propanols</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011994" MajorTopicYN="N">Recombinant Proteins</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">4-Coumaric acid: coenzyme A ligase</Keyword><Keyword MajorTopicYN="N">4-Hydroxycinnamyl alcohols</Keyword><Keyword MajorTopicYN="N">Cinnamoyl coenzyme A reductase</Keyword><Keyword MajorTopicYN="N">Cinnamyl alcohol dehydrogenase</Keyword><Keyword MajorTopicYN="N">Escherichia coli</Keyword><Keyword MajorTopicYN="N">Immobilized whole-cell</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>12</Month><Day>17</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2017</Year><Month>06</Month><Day>07</Day></PubMedPubDate><PubMedPubDate 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