Stereoselective Bioreduction of α-Azido Ketones by Whole Cells of Marine-Derived Fungi
Seven strains of marine-derived fungi (Aspergillus sclerotiorum CBMAI 849, Cladosporium cladosporioides CBMAI 857, Penicillium raistrickii CBMAI 931, Penicillium citrinum CBMA 1186, Mucor racemosus CBMAI 847, Beauveria felina CBMAI 738, and Penicillium oxalicum CBMAI 1185) and terrestrial fungus Pen...
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| Veröffentlicht in: | Marine biotechnology (New York, N.Y.) N.Y.), 2015-12, Vol.17 (6), p.736-742 |
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| creator | Rocha, Lenilson C. Seleghim, Mirna H. R. Comasseto, João V. Sette, Lara D. Porto, André L. M. |
| description | Seven strains of marine-derived fungi (Aspergillus sclerotiorum CBMAI 849, Cladosporium cladosporioides CBMAI 857, Penicillium raistrickii CBMAI 931, Penicillium citrinum CBMA 1186, Mucor racemosus CBMAI 847, Beauveria felina CBMAI 738, and Penicillium oxalicum CBMAI 1185) and terrestrial fungus Penicillium chrysogenum CBMA1199 were screened as catalysts for the asymmetric reduction of α-keto azides 5–8 to their corresponding β-azidophenylethanols 9–12. The marine fungi showed Prelog and anti-Prelog selectivities to the reduction α-keto azides 5–8. The fungi A. sclerotiorum CBMAI 849, C. cladosporioides CBMAI 857, P. raistrickii CBMAI 931, and P. citrinum CBMA 1186 catalyzed the reduction of azido ketone 6 to the corresponding (R)-2-azido-1-(4-methoxyphenyl)ethanol (10) with good conversions (68–100 %) and excellent enantiomeric excesses (>99 % ee) according to Prelog rule. |
| doi_str_mv | 10.1007/s10126-015-9644-x |
| format | Article |
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The fungi A. sclerotiorum CBMAI 849, C. cladosporioides CBMAI 857, P. raistrickii CBMAI 931, and P. citrinum CBMA 1186 catalyzed the reduction of azido ketone 6 to the corresponding (R)-2-azido-1-(4-methoxyphenyl)ethanol (10) with good conversions (68–100 %) and excellent enantiomeric excesses (>99 % ee) according to Prelog rule.</description><identifier>ISSN: 1436-2228</identifier><identifier>EISSN: 1436-2236</identifier><identifier>DOI: 10.1007/s10126-015-9644-x</identifier><identifier>PMID: 26272428</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Aquatic Organisms - metabolism ; Aspergillus ; Aspergillus - metabolism ; Azides - metabolism ; Beauveria ; Beauveria - metabolism ; Biodegradation, Environmental ; Biomedical and Life Sciences ; Catalysis ; Cladosporium - metabolism ; Cladosporium cladosporioides ; Engineering ; Freshwater & Marine Ecology ; Fungi - metabolism ; Ketones - metabolism ; Life Sciences ; Marine ; Microbiology ; Mucor - metabolism ; Mucor racemosus ; Original Article ; Penicillium ; Penicillium - metabolism ; Penicillium chrysogenum ; Penicillium chrysogenum - metabolism ; Penicillium citrinum ; Penicillium oxalicum ; Stereoisomerism ; Zoology</subject><ispartof>Marine biotechnology (New York, N.Y.), 2015-12, Vol.17 (6), p.736-742</ispartof><rights>Springer Science+Business Media New York 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c514t-9ca3d3891e686de721199bfa21919466d3467fdddfc3c7b82d18d6e24a7ddeba3</citedby><cites>FETCH-LOGICAL-c514t-9ca3d3891e686de721199bfa21919466d3467fdddfc3c7b82d18d6e24a7ddeba3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10126-015-9644-x$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10126-015-9644-x$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,781,785,27929,27930,41493,42562,51324</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26272428$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rocha, Lenilson C.</creatorcontrib><creatorcontrib>Seleghim, Mirna H. R.</creatorcontrib><creatorcontrib>Comasseto, João V.</creatorcontrib><creatorcontrib>Sette, Lara D.</creatorcontrib><creatorcontrib>Porto, André L. M.</creatorcontrib><title>Stereoselective Bioreduction of α-Azido Ketones by Whole Cells of Marine-Derived Fungi</title><title>Marine biotechnology (New York, N.Y.)</title><addtitle>Mar Biotechnol</addtitle><addtitle>Mar Biotechnol (NY)</addtitle><description>Seven strains of marine-derived fungi (Aspergillus sclerotiorum CBMAI 849, Cladosporium cladosporioides CBMAI 857, Penicillium raistrickii CBMAI 931, Penicillium citrinum CBMA 1186, Mucor racemosus CBMAI 847, Beauveria felina CBMAI 738, and Penicillium oxalicum CBMAI 1185) and terrestrial fungus Penicillium chrysogenum CBMA1199 were screened as catalysts for the asymmetric reduction of α-keto azides 5–8 to their corresponding β-azidophenylethanols 9–12. The marine fungi showed Prelog and anti-Prelog selectivities to the reduction α-keto azides 5–8. The fungi A. sclerotiorum CBMAI 849, C. cladosporioides CBMAI 857, P. raistrickii CBMAI 931, and P. citrinum CBMA 1186 catalyzed the reduction of azido ketone 6 to the corresponding (R)-2-azido-1-(4-methoxyphenyl)ethanol (10) with good conversions (68–100 %) and excellent enantiomeric excesses (>99 % ee) according to Prelog rule.</description><subject>Aquatic Organisms - metabolism</subject><subject>Aspergillus</subject><subject>Aspergillus - metabolism</subject><subject>Azides - metabolism</subject><subject>Beauveria</subject><subject>Beauveria - metabolism</subject><subject>Biodegradation, Environmental</subject><subject>Biomedical and Life Sciences</subject><subject>Catalysis</subject><subject>Cladosporium - metabolism</subject><subject>Cladosporium cladosporioides</subject><subject>Engineering</subject><subject>Freshwater & Marine Ecology</subject><subject>Fungi - metabolism</subject><subject>Ketones - metabolism</subject><subject>Life Sciences</subject><subject>Marine</subject><subject>Microbiology</subject><subject>Mucor - metabolism</subject><subject>Mucor racemosus</subject><subject>Original Article</subject><subject>Penicillium</subject><subject>Penicillium - metabolism</subject><subject>Penicillium chrysogenum</subject><subject>Penicillium chrysogenum - metabolism</subject><subject>Penicillium citrinum</subject><subject>Penicillium oxalicum</subject><subject>Stereoisomerism</subject><subject>Zoology</subject><issn>1436-2228</issn><issn>1436-2236</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkMtO3TAQhq2KqlzaB-iGZtmNwWM7dryEw62CqguKWFpOPDkE5cTUTirgrXgRnqk-CmWJWI1H_v5fo4-Qr8D2gDG9n4ABV5RBSY2Skt5_IFsghaKcC7Xx-ubVJtlO6ZbljBbsE9nkimsuebVFri9HjBgS9tiM3V8sDrsQ0U95CUMR2uL5iR48dj4U5ziGAVNRPxTXN6HHYoF9n9bITxe7AekRxlzgi5NpWHafycfW9Qm_vMwdcnVy_HtxRi9-nf5YHFzQpgQ5UtM44UVlAFWlPGoOYEzdOg4GjFTKC6l0671vG9HouuIeKq-QS6e9x9qJHfJ97r2L4c-EabSrLjX5MjdgmJIFLUrDSyj1e1DQhhnNMgoz2sSQUsTW3sVu5eKDBWbX6u2s3mb1dq3e3ufM7kv9VK_Qvyb-u84An4GUv4YlRnsbpjhkO2-2fptDrQvWLWOX7NUlZ6AYA6kZMPEPLmCYpA</recordid><startdate>20151201</startdate><enddate>20151201</enddate><creator>Rocha, Lenilson C.</creator><creator>Seleghim, Mirna H. 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M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoselective Bioreduction of α-Azido Ketones by Whole Cells of Marine-Derived Fungi</atitle><jtitle>Marine biotechnology (New York, N.Y.)</jtitle><stitle>Mar Biotechnol</stitle><addtitle>Mar Biotechnol (NY)</addtitle><date>2015-12-01</date><risdate>2015</risdate><volume>17</volume><issue>6</issue><spage>736</spage><epage>742</epage><pages>736-742</pages><issn>1436-2228</issn><eissn>1436-2236</eissn><abstract>Seven strains of marine-derived fungi (Aspergillus sclerotiorum CBMAI 849, Cladosporium cladosporioides CBMAI 857, Penicillium raistrickii CBMAI 931, Penicillium citrinum CBMA 1186, Mucor racemosus CBMAI 847, Beauveria felina CBMAI 738, and Penicillium oxalicum CBMAI 1185) and terrestrial fungus Penicillium chrysogenum CBMA1199 were screened as catalysts for the asymmetric reduction of α-keto azides 5–8 to their corresponding β-azidophenylethanols 9–12. The marine fungi showed Prelog and anti-Prelog selectivities to the reduction α-keto azides 5–8. The fungi A. sclerotiorum CBMAI 849, C. cladosporioides CBMAI 857, P. raistrickii CBMAI 931, and P. citrinum CBMA 1186 catalyzed the reduction of azido ketone 6 to the corresponding (R)-2-azido-1-(4-methoxyphenyl)ethanol (10) with good conversions (68–100 %) and excellent enantiomeric excesses (>99 % ee) according to Prelog rule.</abstract><cop>New York</cop><pub>Springer US</pub><pmid>26272428</pmid><doi>10.1007/s10126-015-9644-x</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Marine biotechnology (New York, N.Y.), 2015-12, Vol.17 (6), p.736-742 |
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| source | MEDLINE; SpringerNature Journals |
| subjects | Aquatic Organisms - metabolism Aspergillus Aspergillus - metabolism Azides - metabolism Beauveria Beauveria - metabolism Biodegradation, Environmental Biomedical and Life Sciences Catalysis Cladosporium - metabolism Cladosporium cladosporioides Engineering Freshwater & Marine Ecology Fungi - metabolism Ketones - metabolism Life Sciences Marine Microbiology Mucor - metabolism Mucor racemosus Original Article Penicillium Penicillium - metabolism Penicillium chrysogenum Penicillium chrysogenum - metabolism Penicillium citrinum Penicillium oxalicum Stereoisomerism Zoology |
| title | Stereoselective Bioreduction of α-Azido Ketones by Whole Cells of Marine-Derived Fungi |
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