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The santalene synthase from Cinnamomum camphora: Reconstruction of a sesquiterpene synthase from a monoterpene synthase
Plant terpene synthases (TPSs) can mediate formation of a large variety of terpenes, and their diversification contributes to the specific chemical profiles of different plant species and chemotypes. Plant genomes often encode a number of related terpene synthases, which can produce very different t...
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| Published in: | Archives of biochemistry and biophysics 2020-11, Vol.695, p.108647-108647, Article 108647 |
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| creator | Di Girolamo, Alice Durairaj, Janani van Houwelingen, Adèle Verstappen, Francel Bosch, Dirk Cankar, Katarina Bouwmeester, Harro de Ridder, Dick van Dijk, Aalt D.J. Beekwilder, Jules |
| description | Plant terpene synthases (TPSs) can mediate formation of a large variety of terpenes, and their diversification contributes to the specific chemical profiles of different plant species and chemotypes. Plant genomes often encode a number of related terpene synthases, which can produce very different terpenes. The relationship between TPS sequence and resulting terpene product is not completely understood. In this work we describe two TPSs from the Camphor tree Cinnamomum camphora (L.) Presl. One of these, CiCaMS, acts as a monoterpene synthase (monoTPS), and mediates the production of myrcene, while the other, CiCaSSy, acts as a sesquiterpene synthase (sesquiTPS), and catalyses the production of α-santalene, β-santalene and trans-α-bergamotene. Interestingly, these enzymes share 97% DNA sequence identity and differ only in 22 amino acid residues out of 553. To understand which residues are essential for the catalysis of monoterpenes resp. sesquiterpenes, a number of hybrid synthases were prepared, and supplemented by a set of single-residue variants. These were tested for their ability to produce monoterpenes and sesquiterpenes by in vivo production of sesquiterpenes in E. coli, and by in vitro enzyme assays. This analysis pinpointed three residues in the sequence which could mediate the change in product specificity from a monoterpene synthase to a sesquiterpene synthase. Another set of three residues defined the sesquiterpene product profile, including the ratios between sesquiterpene products.
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•Two novel highly related terpene synthases for myrcene (CiCaMS) and santalene (CiCaSSy) from Cinnamomum camphora.•Hybrid enzymes of CiCaMS and CiCaSSy identify regions crucial for sesquiterpene synthase activity.•Six mutation of residues is sufficient for converting the myrcene synthase to the santalene synthase. |
| doi_str_mv | 10.1016/j.abb.2020.108647 |
| format | article |
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[Display omitted]
•Two novel highly related terpene synthases for myrcene (CiCaMS) and santalene (CiCaSSy) from Cinnamomum camphora.•Hybrid enzymes of CiCaMS and CiCaSSy identify regions crucial for sesquiterpene synthase activity.•Six mutation of residues is sufficient for converting the myrcene synthase to the santalene synthase.</description><identifier>ISSN: 0003-9861</identifier><identifier>EISSN: 1096-0384</identifier><identifier>DOI: 10.1016/j.abb.2020.108647</identifier><identifier>PMID: 33121934</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Alkyl and Aryl Transferases - chemistry ; Alkyl and Aryl Transferases - genetics ; Alkyl and Aryl Transferases - metabolism ; Cinnamomum camphora ; Cinnamomum camphora - enzymology ; Cinnamomum camphora - genetics ; Escherichia coli - genetics ; Escherichia coli - metabolism ; Hybrid enzymes ; Monoterpene synthase ; Monoterpenes - chemistry ; Monoterpenes - metabolism ; Plant Proteins - chemistry ; Plant Proteins - genetics ; Plant Proteins - metabolism ; Recombinant Proteins - chemistry ; Recombinant Proteins - genetics ; Recombinant Proteins - metabolism ; Santalene synthase ; Sesquiterpene synthase ; Sesquiterpenes - chemistry ; Sesquiterpenes - metabolism ; Terpene</subject><ispartof>Archives of biochemistry and biophysics, 2020-11, Vol.695, p.108647-108647, Article 108647</ispartof><rights>2020 The Authors</rights><rights>Copyright © 2020 The Authors. Published by Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c396t-de78db51d6f2db4861c524ec61edb6f5e0210c10e7dd43204380894d1ee60e3</citedby><cites>FETCH-LOGICAL-c396t-de78db51d6f2db4861c524ec61edb6f5e0210c10e7dd43204380894d1ee60e3</cites><orcidid>0000-0002-4944-4310 ; 0000-0003-3238-4427 ; 0000-0002-1698-4556</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33121934$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Di Girolamo, Alice</creatorcontrib><creatorcontrib>Durairaj, Janani</creatorcontrib><creatorcontrib>van Houwelingen, Adèle</creatorcontrib><creatorcontrib>Verstappen, Francel</creatorcontrib><creatorcontrib>Bosch, Dirk</creatorcontrib><creatorcontrib>Cankar, Katarina</creatorcontrib><creatorcontrib>Bouwmeester, Harro</creatorcontrib><creatorcontrib>de Ridder, Dick</creatorcontrib><creatorcontrib>van Dijk, Aalt D.J.</creatorcontrib><creatorcontrib>Beekwilder, Jules</creatorcontrib><title>The santalene synthase from Cinnamomum camphora: Reconstruction of a sesquiterpene synthase from a monoterpene synthase</title><title>Archives of biochemistry and biophysics</title><addtitle>Arch Biochem Biophys</addtitle><description>Plant terpene synthases (TPSs) can mediate formation of a large variety of terpenes, and their diversification contributes to the specific chemical profiles of different plant species and chemotypes. Plant genomes often encode a number of related terpene synthases, which can produce very different terpenes. The relationship between TPS sequence and resulting terpene product is not completely understood. In this work we describe two TPSs from the Camphor tree Cinnamomum camphora (L.) Presl. One of these, CiCaMS, acts as a monoterpene synthase (monoTPS), and mediates the production of myrcene, while the other, CiCaSSy, acts as a sesquiterpene synthase (sesquiTPS), and catalyses the production of α-santalene, β-santalene and trans-α-bergamotene. Interestingly, these enzymes share 97% DNA sequence identity and differ only in 22 amino acid residues out of 553. To understand which residues are essential for the catalysis of monoterpenes resp. sesquiterpenes, a number of hybrid synthases were prepared, and supplemented by a set of single-residue variants. These were tested for their ability to produce monoterpenes and sesquiterpenes by in vivo production of sesquiterpenes in E. coli, and by in vitro enzyme assays. This analysis pinpointed three residues in the sequence which could mediate the change in product specificity from a monoterpene synthase to a sesquiterpene synthase. Another set of three residues defined the sesquiterpene product profile, including the ratios between sesquiterpene products.
[Display omitted]
•Two novel highly related terpene synthases for myrcene (CiCaMS) and santalene (CiCaSSy) from Cinnamomum camphora.•Hybrid enzymes of CiCaMS and CiCaSSy identify regions crucial for sesquiterpene synthase activity.•Six mutation of residues is sufficient for converting the myrcene synthase to the santalene synthase.</description><subject>Alkyl and Aryl Transferases - chemistry</subject><subject>Alkyl and Aryl Transferases - genetics</subject><subject>Alkyl and Aryl Transferases - metabolism</subject><subject>Cinnamomum camphora</subject><subject>Cinnamomum camphora - enzymology</subject><subject>Cinnamomum camphora - genetics</subject><subject>Escherichia coli - genetics</subject><subject>Escherichia coli - metabolism</subject><subject>Hybrid enzymes</subject><subject>Monoterpene synthase</subject><subject>Monoterpenes - chemistry</subject><subject>Monoterpenes - metabolism</subject><subject>Plant Proteins - chemistry</subject><subject>Plant Proteins - genetics</subject><subject>Plant Proteins - metabolism</subject><subject>Recombinant Proteins - chemistry</subject><subject>Recombinant Proteins - genetics</subject><subject>Recombinant Proteins - metabolism</subject><subject>Santalene synthase</subject><subject>Sesquiterpene synthase</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - metabolism</subject><subject>Terpene</subject><issn>0003-9861</issn><issn>1096-0384</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kEFvEzEQhS0EomnhB3BBPnLZMGM7zi6cUAQtUiUk6N3y2rOKo9hO7V2q_PtulJYDSJxmRvPek97H2DuEJQLqj7ul7fulAHG6W63WL9gCodMNyFa9ZAsAkE3Xarxgl7XuABCVFq_ZhZQosJNqwR7utsSrTaPdU5q3Yxq3thIfSo58E1KyMccpcmfjYZuL_cR_ksupjmVyY8iJ54FbXqneT2Gkcvg3xPKYU_7794a9Guy-0tunecV-fft6t7lpbn9cf998uW2c7PTYeFq3vl-h14PwvZqruJVQ5DSS7_WwIhAIDoHW3ispQMkW2k55JNJA8op9OKceSr6fqI4mhupov7eJ8lSNUCutUAqJsxTPUldyrYUGcygh2nI0COZE2-zMTNucaJsz7dnz_il-6iP5P45nvLPg81lAc8XfgYqpLlBy5EMhNxqfw3_iHwGj2ZIR</recordid><startdate>20201130</startdate><enddate>20201130</enddate><creator>Di Girolamo, Alice</creator><creator>Durairaj, Janani</creator><creator>van Houwelingen, Adèle</creator><creator>Verstappen, Francel</creator><creator>Bosch, Dirk</creator><creator>Cankar, Katarina</creator><creator>Bouwmeester, Harro</creator><creator>de Ridder, Dick</creator><creator>van Dijk, Aalt D.J.</creator><creator>Beekwilder, Jules</creator><general>Elsevier Inc</general><scope>6I.</scope><scope>AAFTH</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-4944-4310</orcidid><orcidid>https://orcid.org/0000-0003-3238-4427</orcidid><orcidid>https://orcid.org/0000-0002-1698-4556</orcidid></search><sort><creationdate>20201130</creationdate><title>The santalene synthase from Cinnamomum camphora: Reconstruction of a sesquiterpene synthase from a monoterpene synthase</title><author>Di Girolamo, Alice ; Durairaj, Janani ; van Houwelingen, Adèle ; Verstappen, Francel ; Bosch, Dirk ; Cankar, Katarina ; Bouwmeester, Harro ; de Ridder, Dick ; van Dijk, Aalt D.J. ; Beekwilder, Jules</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-de78db51d6f2db4861c524ec61edb6f5e0210c10e7dd43204380894d1ee60e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkyl and Aryl Transferases - chemistry</topic><topic>Alkyl and Aryl Transferases - genetics</topic><topic>Alkyl and Aryl Transferases - metabolism</topic><topic>Cinnamomum camphora</topic><topic>Cinnamomum camphora - enzymology</topic><topic>Cinnamomum camphora - genetics</topic><topic>Escherichia coli - genetics</topic><topic>Escherichia coli - metabolism</topic><topic>Hybrid enzymes</topic><topic>Monoterpene synthase</topic><topic>Monoterpenes - chemistry</topic><topic>Monoterpenes - metabolism</topic><topic>Plant Proteins - chemistry</topic><topic>Plant Proteins - genetics</topic><topic>Plant Proteins - metabolism</topic><topic>Recombinant Proteins - chemistry</topic><topic>Recombinant Proteins - genetics</topic><topic>Recombinant Proteins - metabolism</topic><topic>Santalene synthase</topic><topic>Sesquiterpene synthase</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - metabolism</topic><topic>Terpene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Di Girolamo, Alice</creatorcontrib><creatorcontrib>Durairaj, Janani</creatorcontrib><creatorcontrib>van Houwelingen, Adèle</creatorcontrib><creatorcontrib>Verstappen, Francel</creatorcontrib><creatorcontrib>Bosch, Dirk</creatorcontrib><creatorcontrib>Cankar, Katarina</creatorcontrib><creatorcontrib>Bouwmeester, Harro</creatorcontrib><creatorcontrib>de Ridder, Dick</creatorcontrib><creatorcontrib>van Dijk, Aalt D.J.</creatorcontrib><creatorcontrib>Beekwilder, Jules</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Archives of biochemistry and biophysics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Di Girolamo, Alice</au><au>Durairaj, Janani</au><au>van Houwelingen, Adèle</au><au>Verstappen, Francel</au><au>Bosch, Dirk</au><au>Cankar, Katarina</au><au>Bouwmeester, Harro</au><au>de Ridder, Dick</au><au>van Dijk, Aalt D.J.</au><au>Beekwilder, Jules</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The santalene synthase from Cinnamomum camphora: Reconstruction of a sesquiterpene synthase from a monoterpene synthase</atitle><jtitle>Archives of biochemistry and biophysics</jtitle><addtitle>Arch Biochem Biophys</addtitle><date>2020-11-30</date><risdate>2020</risdate><volume>695</volume><spage>108647</spage><epage>108647</epage><pages>108647-108647</pages><artnum>108647</artnum><issn>0003-9861</issn><eissn>1096-0384</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>Plant terpene synthases (TPSs) can mediate formation of a large variety of terpenes, and their diversification contributes to the specific chemical profiles of different plant species and chemotypes. Plant genomes often encode a number of related terpene synthases, which can produce very different terpenes. The relationship between TPS sequence and resulting terpene product is not completely understood. In this work we describe two TPSs from the Camphor tree Cinnamomum camphora (L.) Presl. One of these, CiCaMS, acts as a monoterpene synthase (monoTPS), and mediates the production of myrcene, while the other, CiCaSSy, acts as a sesquiterpene synthase (sesquiTPS), and catalyses the production of α-santalene, β-santalene and trans-α-bergamotene. Interestingly, these enzymes share 97% DNA sequence identity and differ only in 22 amino acid residues out of 553. To understand which residues are essential for the catalysis of monoterpenes resp. sesquiterpenes, a number of hybrid synthases were prepared, and supplemented by a set of single-residue variants. These were tested for their ability to produce monoterpenes and sesquiterpenes by in vivo production of sesquiterpenes in E. coli, and by in vitro enzyme assays. This analysis pinpointed three residues in the sequence which could mediate the change in product specificity from a monoterpene synthase to a sesquiterpene synthase. Another set of three residues defined the sesquiterpene product profile, including the ratios between sesquiterpene products.
[Display omitted]
•Two novel highly related terpene synthases for myrcene (CiCaMS) and santalene (CiCaSSy) from Cinnamomum camphora.•Hybrid enzymes of CiCaMS and CiCaSSy identify regions crucial for sesquiterpene synthase activity.•Six mutation of residues is sufficient for converting the myrcene synthase to the santalene synthase.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>33121934</pmid><doi>10.1016/j.abb.2020.108647</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-4944-4310</orcidid><orcidid>https://orcid.org/0000-0003-3238-4427</orcidid><orcidid>https://orcid.org/0000-0002-1698-4556</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Alkyl and Aryl Transferases - chemistry Alkyl and Aryl Transferases - genetics Alkyl and Aryl Transferases - metabolism Cinnamomum camphora Cinnamomum camphora - enzymology Cinnamomum camphora - genetics Escherichia coli - genetics Escherichia coli - metabolism Hybrid enzymes Monoterpene synthase Monoterpenes - chemistry Monoterpenes - metabolism Plant Proteins - chemistry Plant Proteins - genetics Plant Proteins - metabolism Recombinant Proteins - chemistry Recombinant Proteins - genetics Recombinant Proteins - metabolism Santalene synthase Sesquiterpene synthase Sesquiterpenes - chemistry Sesquiterpenes - metabolism Terpene |
| title | The santalene synthase from Cinnamomum camphora: Reconstruction of a sesquiterpene synthase from a monoterpene synthase |
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