A Regioselective Tryptophan 5-Halogenase Is Involved in Pyrroindomycin Biosynthesis in Streptomyces rugosporus LL-42D005
The antibiotic compound pyrroindomycin B contains an indole ring chlorinated in the 5 position. The indole ring is probably derived from tryptophan, and thus primers derived from conserved regions of tryptophan halogenases were used to amplify and clone a DNA fragment that was then used to isolate a...
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| Veröffentlicht in: | Chemistry & biology 2005-04, Vol.12 (4), p.445-452 |
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| creator | Zehner, Susanne Kotzsch, Alexander Bister, Bojan Süssmuth, Roderich D. Méndez, Carmen Salas, José A. van Pée, Karl-Heinz |
| description | The antibiotic compound pyrroindomycin B contains an indole ring chlorinated in the 5 position. The indole ring is probably derived from tryptophan, and thus primers derived from conserved regions of tryptophan halogenases were used to amplify and clone a DNA fragment that was then used to isolate a tryptophan 5-halogenase gene (
pyrH) from a cosmid library of the pyrroindomycin producer
Streptomyces rugosporus LL-42D005. A gene disruption mutant in the tryptophan 5-halogenase gene no longer produced pyrroindomycin B, but still produced pyrroindomycin A, the nonhalogenated derivative. The halogenase gene could be overexpressed in
Pseudomonas fluorescens BL915 ΔORF1 and was purified to homogeneity by immobilized metal chelate ion affinity chromatography. Chlorinating and brominating activities with tryptophan as a substrate were detected in cell-free extracts and for the purified enzyme. |
| doi_str_mv | 10.1016/j.chembiol.2005.02.005 |
| format | Article |
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pyrH) from a cosmid library of the pyrroindomycin producer
Streptomyces rugosporus LL-42D005. A gene disruption mutant in the tryptophan 5-halogenase gene no longer produced pyrroindomycin B, but still produced pyrroindomycin A, the nonhalogenated derivative. The halogenase gene could be overexpressed in
Pseudomonas fluorescens BL915 ΔORF1 and was purified to homogeneity by immobilized metal chelate ion affinity chromatography. Chlorinating and brominating activities with tryptophan as a substrate were detected in cell-free extracts and for the purified enzyme.</description><identifier>ISSN: 1074-5521</identifier><identifier>EISSN: 1879-1301</identifier><identifier>DOI: 10.1016/j.chembiol.2005.02.005</identifier><identifier>PMID: 15850981</identifier><language>eng</language><publisher>United States: Elsevier Ltd</publisher><subject>Amino Acid Sequence ; Anti-Bacterial Agents - biosynthesis ; Chromatography, High Pressure Liquid ; Cloning, Molecular ; DNA, Fungal - chemistry ; DNA, Fungal - genetics ; Electrophoresis, Polyacrylamide Gel ; Gene Expression Regulation, Enzymologic - genetics ; Genes, Fungal ; Genetic Vectors ; Macrolides - metabolism ; Magnetic Resonance Spectroscopy ; Molecular Sequence Data ; Mutation - genetics ; Oxidoreductases - genetics ; Oxidoreductases - isolation & purification ; Oxidoreductases - metabolism ; Plasmids - genetics ; Reverse Transcriptase Polymerase Chain Reaction ; Spectrometry, Mass, Electrospray Ionization ; Spectrophotometry, Ultraviolet ; Streptomyces - enzymology ; Streptomyces - genetics ; Streptomyces - metabolism</subject><ispartof>Chemistry & biology, 2005-04, Vol.12 (4), p.445-452</ispartof><rights>2005 Elsevier Ltd</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c480t-35ff83f82b8a563702c737ca52e0430ef6bde718453ab389dbf7c736fb540b23</citedby><cites>FETCH-LOGICAL-c480t-35ff83f82b8a563702c737ca52e0430ef6bde718453ab389dbf7c736fb540b23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S1074552105000608$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15850981$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zehner, Susanne</creatorcontrib><creatorcontrib>Kotzsch, Alexander</creatorcontrib><creatorcontrib>Bister, Bojan</creatorcontrib><creatorcontrib>Süssmuth, Roderich D.</creatorcontrib><creatorcontrib>Méndez, Carmen</creatorcontrib><creatorcontrib>Salas, José A.</creatorcontrib><creatorcontrib>van Pée, Karl-Heinz</creatorcontrib><title>A Regioselective Tryptophan 5-Halogenase Is Involved in Pyrroindomycin Biosynthesis in Streptomyces rugosporus LL-42D005</title><title>Chemistry & biology</title><addtitle>Chem Biol</addtitle><description>The antibiotic compound pyrroindomycin B contains an indole ring chlorinated in the 5 position. The indole ring is probably derived from tryptophan, and thus primers derived from conserved regions of tryptophan halogenases were used to amplify and clone a DNA fragment that was then used to isolate a tryptophan 5-halogenase gene (
pyrH) from a cosmid library of the pyrroindomycin producer
Streptomyces rugosporus LL-42D005. A gene disruption mutant in the tryptophan 5-halogenase gene no longer produced pyrroindomycin B, but still produced pyrroindomycin A, the nonhalogenated derivative. The halogenase gene could be overexpressed in
Pseudomonas fluorescens BL915 ΔORF1 and was purified to homogeneity by immobilized metal chelate ion affinity chromatography. Chlorinating and brominating activities with tryptophan as a substrate were detected in cell-free extracts and for the purified enzyme.</description><subject>Amino Acid Sequence</subject><subject>Anti-Bacterial Agents - biosynthesis</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Cloning, Molecular</subject><subject>DNA, Fungal - chemistry</subject><subject>DNA, Fungal - genetics</subject><subject>Electrophoresis, Polyacrylamide Gel</subject><subject>Gene Expression Regulation, Enzymologic - genetics</subject><subject>Genes, Fungal</subject><subject>Genetic Vectors</subject><subject>Macrolides - metabolism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Sequence Data</subject><subject>Mutation - genetics</subject><subject>Oxidoreductases - genetics</subject><subject>Oxidoreductases - isolation & purification</subject><subject>Oxidoreductases - metabolism</subject><subject>Plasmids - genetics</subject><subject>Reverse Transcriptase Polymerase Chain Reaction</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Streptomyces - enzymology</subject><subject>Streptomyces - genetics</subject><subject>Streptomyces - metabolism</subject><issn>1074-5521</issn><issn>1879-1301</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEFv1DAQhSNERUvhL1Q-cUsY23HsvVFaoCut1Krs3XKcya5XSRzsZEX-PV7tIo6c3ozmzRv7y7I7CgUFWn0-FHaPfe18VzAAUQArkrzJbqiSq5xyoG9TDbLMhWD0Onsf4wEAqFpV77JrKpSAlaI32e978oo75yN2aCd3RLINyzj5cW8GIvIn0_kdDiYiWUeyHo6-O2JD3EBelhC8GxrfLza1X1PEMkx7jC6exj-ngCkmDTGSMO98HH2YI9ls8pI9pqd-yK5a00X8eNHbbPv92_bhKd88_1g_3G9yWyqYci7aVvFWsVoZUXEJzEourREMoeSAbVU3KKkqBTc1V6umbmVyVG0tSqgZv80-nWPH4H_NGCfdu2ix68yAfo66klKWlYBkrM5GG3yMAVs9BtebsGgK-oRcH_Rf5PqEXAPTSdLi3eXCXPfY_Fu7ME6GL2cDpm8eHQYdrcPBYuNCYq4b7_534w-PxJcK</recordid><startdate>20050401</startdate><enddate>20050401</enddate><creator>Zehner, Susanne</creator><creator>Kotzsch, Alexander</creator><creator>Bister, Bojan</creator><creator>Süssmuth, Roderich D.</creator><creator>Méndez, Carmen</creator><creator>Salas, José A.</creator><creator>van Pée, Karl-Heinz</creator><general>Elsevier Ltd</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></search><sort><creationdate>20050401</creationdate><title>A Regioselective Tryptophan 5-Halogenase Is Involved in Pyrroindomycin Biosynthesis in Streptomyces rugosporus LL-42D005</title><author>Zehner, Susanne ; Kotzsch, Alexander ; Bister, Bojan ; Süssmuth, Roderich D. ; Méndez, Carmen ; Salas, José A. ; van Pée, Karl-Heinz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c480t-35ff83f82b8a563702c737ca52e0430ef6bde718453ab389dbf7c736fb540b23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Amino Acid Sequence</topic><topic>Anti-Bacterial Agents - biosynthesis</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Cloning, Molecular</topic><topic>DNA, Fungal - chemistry</topic><topic>DNA, Fungal - genetics</topic><topic>Electrophoresis, Polyacrylamide Gel</topic><topic>Gene Expression Regulation, Enzymologic - genetics</topic><topic>Genes, Fungal</topic><topic>Genetic Vectors</topic><topic>Macrolides - metabolism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Sequence Data</topic><topic>Mutation - genetics</topic><topic>Oxidoreductases - genetics</topic><topic>Oxidoreductases - isolation & purification</topic><topic>Oxidoreductases - metabolism</topic><topic>Plasmids - genetics</topic><topic>Reverse Transcriptase Polymerase Chain Reaction</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Streptomyces - enzymology</topic><topic>Streptomyces - genetics</topic><topic>Streptomyces - metabolism</topic><toplevel>online_resources</toplevel><creatorcontrib>Zehner, Susanne</creatorcontrib><creatorcontrib>Kotzsch, Alexander</creatorcontrib><creatorcontrib>Bister, Bojan</creatorcontrib><creatorcontrib>Süssmuth, Roderich D.</creatorcontrib><creatorcontrib>Méndez, Carmen</creatorcontrib><creatorcontrib>Salas, José A.</creatorcontrib><creatorcontrib>van Pée, Karl-Heinz</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>Chemistry & biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zehner, Susanne</au><au>Kotzsch, Alexander</au><au>Bister, Bojan</au><au>Süssmuth, Roderich D.</au><au>Méndez, Carmen</au><au>Salas, José A.</au><au>van Pée, Karl-Heinz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Regioselective Tryptophan 5-Halogenase Is Involved in Pyrroindomycin Biosynthesis in Streptomyces rugosporus LL-42D005</atitle><jtitle>Chemistry & biology</jtitle><addtitle>Chem Biol</addtitle><date>2005-04-01</date><risdate>2005</risdate><volume>12</volume><issue>4</issue><spage>445</spage><epage>452</epage><pages>445-452</pages><issn>1074-5521</issn><eissn>1879-1301</eissn><abstract>The antibiotic compound pyrroindomycin B contains an indole ring chlorinated in the 5 position. The indole ring is probably derived from tryptophan, and thus primers derived from conserved regions of tryptophan halogenases were used to amplify and clone a DNA fragment that was then used to isolate a tryptophan 5-halogenase gene (
pyrH) from a cosmid library of the pyrroindomycin producer
Streptomyces rugosporus LL-42D005. A gene disruption mutant in the tryptophan 5-halogenase gene no longer produced pyrroindomycin B, but still produced pyrroindomycin A, the nonhalogenated derivative. The halogenase gene could be overexpressed in
Pseudomonas fluorescens BL915 ΔORF1 and was purified to homogeneity by immobilized metal chelate ion affinity chromatography. Chlorinating and brominating activities with tryptophan as a substrate were detected in cell-free extracts and for the purified enzyme.</abstract><cop>United States</cop><pub>Elsevier Ltd</pub><pmid>15850981</pmid><doi>10.1016/j.chembiol.2005.02.005</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Cell Press Free Archives; Elsevier ScienceDirect Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Amino Acid Sequence Anti-Bacterial Agents - biosynthesis Chromatography, High Pressure Liquid Cloning, Molecular DNA, Fungal - chemistry DNA, Fungal - genetics Electrophoresis, Polyacrylamide Gel Gene Expression Regulation, Enzymologic - genetics Genes, Fungal Genetic Vectors Macrolides - metabolism Magnetic Resonance Spectroscopy Molecular Sequence Data Mutation - genetics Oxidoreductases - genetics Oxidoreductases - isolation & purification Oxidoreductases - metabolism Plasmids - genetics Reverse Transcriptase Polymerase Chain Reaction Spectrometry, Mass, Electrospray Ionization Spectrophotometry, Ultraviolet Streptomyces - enzymology Streptomyces - genetics Streptomyces - metabolism |
| title | A Regioselective Tryptophan 5-Halogenase Is Involved in Pyrroindomycin Biosynthesis in Streptomyces rugosporus LL-42D005 |
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