Expression and Substrate Range of Streptomyces Vanillate Demethylase
Vanillate is converted to protocatechuate by an O-demethylase consisting of VanA and VanB in Streptomyces sp. NL15-2K. In this study, vanillate demethylase from this strain was functionally expressed in Escherichia coli, and its substrate range for vanillate analogs was determined by an in vivo assa...
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| Veröffentlicht in: | Biological & pharmaceutical bulletin 2014/09/01, Vol.37(9), pp.1564-1568 |
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| creator | Nishimura, Motohiro Nishimura, Yoshio Abe, Chinatsu Kohhata, Mayuko |
| description | Vanillate is converted to protocatechuate by an O-demethylase consisting of VanA and VanB in Streptomyces sp. NL15-2K. In this study, vanillate demethylase from this strain was functionally expressed in Escherichia coli, and its substrate range for vanillate analogs was determined by an in vivo assay using recombinant whole cells. Among aromatic methyl ethers, vanillate, syringate, m-anisate, and veratrate were good substrates, whereas ferulate, vanillin, and guaiacol were not recognized by Streptomyces vanillate demethylase. After vanillate, 4-hydroxy-3-methylbenzoate was a better substrate than m-anisate and veratrate, and the 3-methyl group was efficiently oxidized to a hydroxymethyl group. These observations suggest that the combination of a carboxyl group on the benzene ring and a hydroxyl group in the para-position relative to the carboxyl group may be preferable for substrate recognition by the enzyme. 1H-NMR analysis showed that the demethylation product of veratrate was isovanillate rather than vanillate. Therefore, it was concluded that O-demethylation of veratrate by Streptomyces vanillate demethylase occurred only at the meta-position relative to the carboxyl group. |
| doi_str_mv | 10.1248/bpb.b14-00337 |
| format | Article |
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NL15-2K. In this study, vanillate demethylase from this strain was functionally expressed in Escherichia coli, and its substrate range for vanillate analogs was determined by an in vivo assay using recombinant whole cells. Among aromatic methyl ethers, vanillate, syringate, m-anisate, and veratrate were good substrates, whereas ferulate, vanillin, and guaiacol were not recognized by Streptomyces vanillate demethylase. After vanillate, 4-hydroxy-3-methylbenzoate was a better substrate than m-anisate and veratrate, and the 3-methyl group was efficiently oxidized to a hydroxymethyl group. These observations suggest that the combination of a carboxyl group on the benzene ring and a hydroxyl group in the para-position relative to the carboxyl group may be preferable for substrate recognition by the enzyme. 1H-NMR analysis showed that the demethylation product of veratrate was isovanillate rather than vanillate. Therefore, it was concluded that O-demethylation of veratrate by Streptomyces vanillate demethylase occurred only at the meta-position relative to the carboxyl group.</description><identifier>ISSN: 0918-6158</identifier><identifier>EISSN: 1347-5215</identifier><identifier>DOI: 10.1248/bpb.b14-00337</identifier><identifier>PMID: 25008238</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Escherichia coli ; Escherichia coli - enzymology ; Escherichia coli - genetics ; expression ; Oxidoreductases, O-Demethylating - genetics ; Oxidoreductases, O-Demethylating - metabolism ; Plasmids ; Streptomyces ; Streptomyces - enzymology ; Streptomyces - genetics ; substrate range ; vanillate demethylase ; Vanillic Acid - analogs & derivatives ; Vanillic Acid - metabolism</subject><ispartof>Biological and Pharmaceutical Bulletin, 2014/09/01, Vol.37(9), pp.1564-1568</ispartof><rights>2014 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c711t-1f90b48ebf3df02076c20f9e7d5f899874696a74db99d58108028b9d9220aa323</citedby><cites>FETCH-LOGICAL-c711t-1f90b48ebf3df02076c20f9e7d5f899874696a74db99d58108028b9d9220aa323</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25008238$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nishimura, Motohiro</creatorcontrib><creatorcontrib>Nishimura, Yoshio</creatorcontrib><creatorcontrib>Abe, Chinatsu</creatorcontrib><creatorcontrib>Kohhata, Mayuko</creatorcontrib><creatorcontrib>Yasuda Women's University</creatorcontrib><creatorcontrib>Department of Pharmaceutical Chemistry</creatorcontrib><creatorcontrib>Faculty of Pharmacy</creatorcontrib><title>Expression and Substrate Range of Streptomyces Vanillate Demethylase</title><title>Biological & pharmaceutical bulletin</title><addtitle>Biol Pharm Bull</addtitle><description>Vanillate is converted to protocatechuate by an O-demethylase consisting of VanA and VanB in Streptomyces sp. NL15-2K. In this study, vanillate demethylase from this strain was functionally expressed in Escherichia coli, and its substrate range for vanillate analogs was determined by an in vivo assay using recombinant whole cells. Among aromatic methyl ethers, vanillate, syringate, m-anisate, and veratrate were good substrates, whereas ferulate, vanillin, and guaiacol were not recognized by Streptomyces vanillate demethylase. After vanillate, 4-hydroxy-3-methylbenzoate was a better substrate than m-anisate and veratrate, and the 3-methyl group was efficiently oxidized to a hydroxymethyl group. These observations suggest that the combination of a carboxyl group on the benzene ring and a hydroxyl group in the para-position relative to the carboxyl group may be preferable for substrate recognition by the enzyme. 1H-NMR analysis showed that the demethylation product of veratrate was isovanillate rather than vanillate. Therefore, it was concluded that O-demethylation of veratrate by Streptomyces vanillate demethylase occurred only at the meta-position relative to the carboxyl group.</description><subject>Escherichia coli</subject><subject>Escherichia coli - enzymology</subject><subject>Escherichia coli - genetics</subject><subject>expression</subject><subject>Oxidoreductases, O-Demethylating - genetics</subject><subject>Oxidoreductases, O-Demethylating - metabolism</subject><subject>Plasmids</subject><subject>Streptomyces</subject><subject>Streptomyces - enzymology</subject><subject>Streptomyces - genetics</subject><subject>substrate range</subject><subject>vanillate demethylase</subject><subject>Vanillic Acid - analogs & derivatives</subject><subject>Vanillic Acid - metabolism</subject><issn>0918-6158</issn><issn>1347-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUFv1DAQhS0EotuFI1cUiQuXlLEdx_YRbUuLVAmJAlfLTiZtVkkcbEdi_z3epiwSFy7jw_v05nkeIW8oXFBWqQ9udheOViUA5_IZ2VBeyVIwKp6TDWiqypoKdUbOY9wDgATGX5IzJgAU42pDLq9-zQFj7P1U2Kkt7hYXU7AJi692usfCd8VdCjgnPx4ajMUPO_XDcNQvccT0cBhsxFfkRWeHiK-f3i35_unq2-6mvP1y_Xn38bZsJKWppJ0GVyl0HW87YCDrhkGnUbaiU1orWdW6trJqndatUBQUMOV0qxkDaznjW_J-9Z2D_7lgTGbsY4M5z4R-iYbKmnEhlZD_R4XQALoWIqPv_kH3fglT_kg2FLwSnObjbkm5Uk3wMQbszBz60YaDoWCOTZjchMlNmMcmMv_2yXVxI7Yn-s_pM3C9AlntGzv4aegn_Lu7idL1fvCGwWoqQRtgLEevq-PILrSWnGen3eq0j8ne42mVDalvBnwMxqXRx3EKeFKbBxsMTvw30G2wOg</recordid><startdate>2014</startdate><enddate>2014</enddate><creator>Nishimura, Motohiro</creator><creator>Nishimura, Yoshio</creator><creator>Abe, Chinatsu</creator><creator>Kohhata, Mayuko</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope><scope>7QL</scope><scope>C1K</scope></search><sort><creationdate>2014</creationdate><title>Expression and Substrate Range of Streptomyces Vanillate Demethylase</title><author>Nishimura, Motohiro ; Nishimura, Yoshio ; Abe, Chinatsu ; Kohhata, Mayuko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c711t-1f90b48ebf3df02076c20f9e7d5f899874696a74db99d58108028b9d9220aa323</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Escherichia coli</topic><topic>Escherichia coli - enzymology</topic><topic>Escherichia coli - genetics</topic><topic>expression</topic><topic>Oxidoreductases, O-Demethylating - genetics</topic><topic>Oxidoreductases, O-Demethylating - metabolism</topic><topic>Plasmids</topic><topic>Streptomyces</topic><topic>Streptomyces - enzymology</topic><topic>Streptomyces - genetics</topic><topic>substrate range</topic><topic>vanillate demethylase</topic><topic>Vanillic Acid - analogs & derivatives</topic><topic>Vanillic Acid - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nishimura, Motohiro</creatorcontrib><creatorcontrib>Nishimura, Yoshio</creatorcontrib><creatorcontrib>Abe, Chinatsu</creatorcontrib><creatorcontrib>Kohhata, Mayuko</creatorcontrib><creatorcontrib>Yasuda Women's University</creatorcontrib><creatorcontrib>Department of Pharmaceutical Chemistry</creatorcontrib><creatorcontrib>Faculty of Pharmacy</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Biological & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nishimura, Motohiro</au><au>Nishimura, Yoshio</au><au>Abe, Chinatsu</au><au>Kohhata, Mayuko</au><aucorp>Yasuda Women's University</aucorp><aucorp>Department of Pharmaceutical Chemistry</aucorp><aucorp>Faculty of Pharmacy</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Expression and Substrate Range of Streptomyces Vanillate Demethylase</atitle><jtitle>Biological & pharmaceutical bulletin</jtitle><addtitle>Biol Pharm Bull</addtitle><date>2014</date><risdate>2014</risdate><volume>37</volume><issue>9</issue><spage>1564</spage><epage>1568</epage><pages>1564-1568</pages><issn>0918-6158</issn><eissn>1347-5215</eissn><abstract>Vanillate is converted to protocatechuate by an O-demethylase consisting of VanA and VanB in Streptomyces sp. NL15-2K. In this study, vanillate demethylase from this strain was functionally expressed in Escherichia coli, and its substrate range for vanillate analogs was determined by an in vivo assay using recombinant whole cells. Among aromatic methyl ethers, vanillate, syringate, m-anisate, and veratrate were good substrates, whereas ferulate, vanillin, and guaiacol were not recognized by Streptomyces vanillate demethylase. After vanillate, 4-hydroxy-3-methylbenzoate was a better substrate than m-anisate and veratrate, and the 3-methyl group was efficiently oxidized to a hydroxymethyl group. These observations suggest that the combination of a carboxyl group on the benzene ring and a hydroxyl group in the para-position relative to the carboxyl group may be preferable for substrate recognition by the enzyme. 1H-NMR analysis showed that the demethylation product of veratrate was isovanillate rather than vanillate. 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| subjects | Escherichia coli Escherichia coli - enzymology Escherichia coli - genetics expression Oxidoreductases, O-Demethylating - genetics Oxidoreductases, O-Demethylating - metabolism Plasmids Streptomyces Streptomyces - enzymology Streptomyces - genetics substrate range vanillate demethylase Vanillic Acid - analogs & derivatives Vanillic Acid - metabolism |
| title | Expression and Substrate Range of Streptomyces Vanillate Demethylase |
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