Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis
An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from Penicillium chrysogenum E01-10/3 and expressed as a soluble protein in Escherichia coli . The enzyme efficiently performed the oxidative dearomatisation of sorbicillin and dihydrosorbicillin to give sorbicillinol and dihydrosorbici...
Gespeichert in:
| Veröffentlicht in: | Chemical science (Cambridge) 2014-01, Vol.5 (2), p.523-527 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 527 |
|---|---|
| container_issue | 2 |
| container_start_page | 523 |
| container_title | Chemical science (Cambridge) |
| container_volume | 5 |
| creator | Fahad, Ahmed al Abood, Amira Fisch, Katja M. Osipow, Anna Davison, Jack Avramović, Marija Butts, Craig P. Piel, Jörn Simpson, Thomas J. Cox, Russell J. |
| description | An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from
Penicillium chrysogenum
E01-10/3 and expressed as a soluble protein in
Escherichia coli
. The enzyme efficiently performed the oxidative dearomatisation of sorbicillin and dihydrosorbicillin to give sorbicillinol and dihydrosorbicillinol respectively. Bioinformatic examination of the gene cluster surrounding SorbC indicated the presence of two polyketide synthase (PKS) encoding genes designated
sorbA
and
sorbB
. The gene
sorbA
-encodes a highly reducing iterative PKS while SorbB encodes a non-reducing iterative PKS which features a reductive release domain usually involved in the production of polyketide aldehydes. Using these observations and previously reported results from isotopic feeding experiments a new and simpler biosynthetic route to the sorbicillin class of secondary metabolites is proposed which is consistent with all reported experimental results. |
| doi_str_mv | 10.1039/C3SC52911H |
| format | Article |
| fullrecord | <record><control><sourceid>pubmedcentral_cross</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4285102</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>pubmedcentral_primary_oai_pubmedcentral_nih_gov_4285102</sourcerecordid><originalsourceid>FETCH-LOGICAL-c429t-71d45d80f0057a6559d61deb28bbcda3cceb35530b04d8c5da1c7b9ab56b42f83</originalsourceid><addsrcrecordid>eNpVkM1Lw0AQxRdRbKm9-BfsWYjO7mby4UGQYK1Q6EE9L_sVu5pmSzYW898bqVR8MLwHM_M7PEIuGVwzEOVNJZ4r5CVjyxMy5ZCyJENRnh4zhwmZx_gOo4RgyPNzMuGIBXAGU7JYf3mrer931DrVhe2Y4zihvaX9xtEPN9DYux0NNY2h0974pvFt8JZqH-LQjkfRxwtyVqsmuvmvz8jr4uGlWiar9eNTdb9KTMrLPsmZTdEWUANgrjLE0mbMOs0LrY1VwhinBaIADaktDFrFTK5LpTHTKa8LMSN3B-7uU2-dNa7tO9XIXee3qhtkUF7-37R-I9_CXqa8QAZ8BFwdAKYLMXauPv4ykD-Fyr9CxTfD7GkY</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis</title><source>Royal Society Of Chemistry Journals 2008-</source><source>PubMed Central</source><source>PubMed Central Open Access</source><creator>Fahad, Ahmed al ; Abood, Amira ; Fisch, Katja M. ; Osipow, Anna ; Davison, Jack ; Avramović, Marija ; Butts, Craig P. ; Piel, Jörn ; Simpson, Thomas J. ; Cox, Russell J.</creator><creatorcontrib>Fahad, Ahmed al ; Abood, Amira ; Fisch, Katja M. ; Osipow, Anna ; Davison, Jack ; Avramović, Marija ; Butts, Craig P. ; Piel, Jörn ; Simpson, Thomas J. ; Cox, Russell J.</creatorcontrib><description>An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from
Penicillium chrysogenum
E01-10/3 and expressed as a soluble protein in
Escherichia coli
. The enzyme efficiently performed the oxidative dearomatisation of sorbicillin and dihydrosorbicillin to give sorbicillinol and dihydrosorbicillinol respectively. Bioinformatic examination of the gene cluster surrounding SorbC indicated the presence of two polyketide synthase (PKS) encoding genes designated
sorbA
and
sorbB
. The gene
sorbA
-encodes a highly reducing iterative PKS while SorbB encodes a non-reducing iterative PKS which features a reductive release domain usually involved in the production of polyketide aldehydes. Using these observations and previously reported results from isotopic feeding experiments a new and simpler biosynthetic route to the sorbicillin class of secondary metabolites is proposed which is consistent with all reported experimental results.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/C3SC52911H</identifier><identifier>PMID: 25580210</identifier><language>eng</language><publisher>Royal Society of Chemistry</publisher><subject>Chemistry</subject><ispartof>Chemical science (Cambridge), 2014-01, Vol.5 (2), p.523-527</ispartof><rights>This journal is © The Royal Society of Chemistry 2013 2013</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-71d45d80f0057a6559d61deb28bbcda3cceb35530b04d8c5da1c7b9ab56b42f83</citedby><cites>FETCH-LOGICAL-c429t-71d45d80f0057a6559d61deb28bbcda3cceb35530b04d8c5da1c7b9ab56b42f83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4285102/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC4285102/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,724,777,781,882,27905,27906,53772,53774</link.rule.ids></links><search><creatorcontrib>Fahad, Ahmed al</creatorcontrib><creatorcontrib>Abood, Amira</creatorcontrib><creatorcontrib>Fisch, Katja M.</creatorcontrib><creatorcontrib>Osipow, Anna</creatorcontrib><creatorcontrib>Davison, Jack</creatorcontrib><creatorcontrib>Avramović, Marija</creatorcontrib><creatorcontrib>Butts, Craig P.</creatorcontrib><creatorcontrib>Piel, Jörn</creatorcontrib><creatorcontrib>Simpson, Thomas J.</creatorcontrib><creatorcontrib>Cox, Russell J.</creatorcontrib><title>Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis</title><title>Chemical science (Cambridge)</title><description>An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from
Penicillium chrysogenum
E01-10/3 and expressed as a soluble protein in
Escherichia coli
. The enzyme efficiently performed the oxidative dearomatisation of sorbicillin and dihydrosorbicillin to give sorbicillinol and dihydrosorbicillinol respectively. Bioinformatic examination of the gene cluster surrounding SorbC indicated the presence of two polyketide synthase (PKS) encoding genes designated
sorbA
and
sorbB
. The gene
sorbA
-encodes a highly reducing iterative PKS while SorbB encodes a non-reducing iterative PKS which features a reductive release domain usually involved in the production of polyketide aldehydes. Using these observations and previously reported results from isotopic feeding experiments a new and simpler biosynthetic route to the sorbicillin class of secondary metabolites is proposed which is consistent with all reported experimental results.</description><subject>Chemistry</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpVkM1Lw0AQxRdRbKm9-BfsWYjO7mby4UGQYK1Q6EE9L_sVu5pmSzYW898bqVR8MLwHM_M7PEIuGVwzEOVNJZ4r5CVjyxMy5ZCyJENRnh4zhwmZx_gOo4RgyPNzMuGIBXAGU7JYf3mrer931DrVhe2Y4zihvaX9xtEPN9DYux0NNY2h0974pvFt8JZqH-LQjkfRxwtyVqsmuvmvz8jr4uGlWiar9eNTdb9KTMrLPsmZTdEWUANgrjLE0mbMOs0LrY1VwhinBaIADaktDFrFTK5LpTHTKa8LMSN3B-7uU2-dNa7tO9XIXee3qhtkUF7-37R-I9_CXqa8QAZ8BFwdAKYLMXauPv4ykD-Fyr9CxTfD7GkY</recordid><startdate>20140101</startdate><enddate>20140101</enddate><creator>Fahad, Ahmed al</creator><creator>Abood, Amira</creator><creator>Fisch, Katja M.</creator><creator>Osipow, Anna</creator><creator>Davison, Jack</creator><creator>Avramović, Marija</creator><creator>Butts, Craig P.</creator><creator>Piel, Jörn</creator><creator>Simpson, Thomas J.</creator><creator>Cox, Russell J.</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>5PM</scope></search><sort><creationdate>20140101</creationdate><title>Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis</title><author>Fahad, Ahmed al ; Abood, Amira ; Fisch, Katja M. ; Osipow, Anna ; Davison, Jack ; Avramović, Marija ; Butts, Craig P. ; Piel, Jörn ; Simpson, Thomas J. ; Cox, Russell J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-71d45d80f0057a6559d61deb28bbcda3cceb35530b04d8c5da1c7b9ab56b42f83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fahad, Ahmed al</creatorcontrib><creatorcontrib>Abood, Amira</creatorcontrib><creatorcontrib>Fisch, Katja M.</creatorcontrib><creatorcontrib>Osipow, Anna</creatorcontrib><creatorcontrib>Davison, Jack</creatorcontrib><creatorcontrib>Avramović, Marija</creatorcontrib><creatorcontrib>Butts, Craig P.</creatorcontrib><creatorcontrib>Piel, Jörn</creatorcontrib><creatorcontrib>Simpson, Thomas J.</creatorcontrib><creatorcontrib>Cox, Russell J.</creatorcontrib><collection>CrossRef</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fahad, Ahmed al</au><au>Abood, Amira</au><au>Fisch, Katja M.</au><au>Osipow, Anna</au><au>Davison, Jack</au><au>Avramović, Marija</au><au>Butts, Craig P.</au><au>Piel, Jörn</au><au>Simpson, Thomas J.</au><au>Cox, Russell J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2014-01-01</date><risdate>2014</risdate><volume>5</volume><issue>2</issue><spage>523</spage><epage>527</epage><pages>523-527</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from
Penicillium chrysogenum
E01-10/3 and expressed as a soluble protein in
Escherichia coli
. The enzyme efficiently performed the oxidative dearomatisation of sorbicillin and dihydrosorbicillin to give sorbicillinol and dihydrosorbicillinol respectively. Bioinformatic examination of the gene cluster surrounding SorbC indicated the presence of two polyketide synthase (PKS) encoding genes designated
sorbA
and
sorbB
. The gene
sorbA
-encodes a highly reducing iterative PKS while SorbB encodes a non-reducing iterative PKS which features a reductive release domain usually involved in the production of polyketide aldehydes. Using these observations and previously reported results from isotopic feeding experiments a new and simpler biosynthetic route to the sorbicillin class of secondary metabolites is proposed which is consistent with all reported experimental results.</abstract><pub>Royal Society of Chemistry</pub><pmid>25580210</pmid><doi>10.1039/C3SC52911H</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2014-01, Vol.5 (2), p.523-527 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_4285102 |
| source | Royal Society Of Chemistry Journals 2008-; PubMed Central; PubMed Central Open Access |
| subjects | Chemistry |
| title | Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-17T16%3A30%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmedcentral_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Oxidative%20dearomatisation:%20the%20key%20step%20of%20sorbicillinoid%20biosynthesis&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Fahad,%20Ahmed%20al&rft.date=2014-01-01&rft.volume=5&rft.issue=2&rft.spage=523&rft.epage=527&rft.pages=523-527&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/C3SC52911H&rft_dat=%3Cpubmedcentral_cross%3Epubmedcentral_primary_oai_pubmedcentral_nih_gov_4285102%3C/pubmedcentral_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/25580210&rfr_iscdi=true |