Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)‐cyclohexyl(phenyl)methanol
In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols....
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2019-03, Vol.31 (3), p.211-218 |
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| creator | Şahin, Engin Serencam, Hüseyin Dertli, Enes |
| description | In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)‐cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)‐cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. This study demonstrates the first example of the effective synthesis of (S)‐cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale. |
| doi_str_mv | 10.1002/chir.23048 |
| format | Article |
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Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)‐cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)‐cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. This study demonstrates the first example of the effective synthesis of (S)‐cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.23048</identifier><identifier>PMID: 30633374</identifier><language>eng</language><publisher>United States: Wiley Subscription Services, Inc</publisher><subject>Alcohols ; asymmetric reduction ; biocatalyst ; Biocatalysts ; biotransformations ; chiral aryl methanols ; Enantiomers ; enantioselectivity ; Ketones ; Lactobacillus paracasei ; Methanol ; Reducing agents ; Reduction ; Strains (organisms) ; Substrates</subject><ispartof>Chirality (New York, N.Y.), 2019-03, Vol.31 (3), p.211-218</ispartof><rights>2019 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3578-d802f88c650e48974d7c6686d354b316a3e3a1a8769344b0096e1e6c96559c8c3</citedby><cites>FETCH-LOGICAL-c3578-d802f88c650e48974d7c6686d354b316a3e3a1a8769344b0096e1e6c96559c8c3</cites><orcidid>0000-0002-3723-1705</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchir.23048$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchir.23048$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30633374$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Şahin, Engin</creatorcontrib><creatorcontrib>Serencam, Hüseyin</creatorcontrib><creatorcontrib>Dertli, Enes</creatorcontrib><title>Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)‐cyclohexyl(phenyl)methanol</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. 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This study demonstrates the first example of the effective synthesis of (S)‐cyclohexyl(phenyl)methanol by the L paracasei BD101 as a biocatalyst in preparative scale.</description><subject>Alcohols</subject><subject>asymmetric reduction</subject><subject>biocatalyst</subject><subject>Biocatalysts</subject><subject>biotransformations</subject><subject>chiral aryl methanols</subject><subject>Enantiomers</subject><subject>enantioselectivity</subject><subject>Ketones</subject><subject>Lactobacillus paracasei</subject><subject>Methanol</subject><subject>Reducing agents</subject><subject>Reduction</subject><subject>Strains (organisms)</subject><subject>Substrates</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp90c1O3DAQB3ALFcFCufAAlaVelkqh4_gjzrFd2oK0ElI_BLfI68wqQU4c7ESQWx-BZ-yTNOnSHjj0NJff_DWjPyGnDM4ZQPreVnU4TzkIvUcWTKaQKK5uX5EF6DxPAER6SI5ivAOAXHFxQA45KM55JhZkvKm8Q2rROWq6ztXW9LVvqd_StbG93xhbOzdE2plgrIlY048XDBjtPe2CLweLFFvTTksNhmnbuZF2Q0C6_Hb26-eTHa3zFT6ObtlV2I7urMG-Mq13r8n-1riIJ8_zmPz4_On76jJZX3-5Wn1YJ5bLTCelhnSrtVUSUOg8E2VmldKq5FJsOFOGIzfM6EzlXIjN_CIyVDZXUuZWW35Mlrvc6dz7AWNfNHWc_zUt-iEWKctyriQDOdG3L-idH0I7XTcpzZiSWTardztlg48x4LboQt2YMBYMirmQYi6k-FPIhN88Rw6bBst_9G8DE2A78FA7HP8TVawur77uQn8DyiSWEw</recordid><startdate>201903</startdate><enddate>201903</enddate><creator>Şahin, Engin</creator><creator>Serencam, Hüseyin</creator><creator>Dertli, Enes</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7QR</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3723-1705</orcidid></search><sort><creationdate>201903</creationdate><title>Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)‐cyclohexyl(phenyl)methanol</title><author>Şahin, Engin ; Serencam, Hüseyin ; Dertli, Enes</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3578-d802f88c650e48974d7c6686d354b316a3e3a1a8769344b0096e1e6c96559c8c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alcohols</topic><topic>asymmetric reduction</topic><topic>biocatalyst</topic><topic>Biocatalysts</topic><topic>biotransformations</topic><topic>chiral aryl methanols</topic><topic>Enantiomers</topic><topic>enantioselectivity</topic><topic>Ketones</topic><topic>Lactobacillus paracasei</topic><topic>Methanol</topic><topic>Reducing agents</topic><topic>Reduction</topic><topic>Strains (organisms)</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Şahin, Engin</creatorcontrib><creatorcontrib>Serencam, Hüseyin</creatorcontrib><creatorcontrib>Dertli, Enes</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Şahin, Engin</au><au>Serencam, Hüseyin</au><au>Dertli, Enes</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)‐cyclohexyl(phenyl)methanol</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2019-03</date><risdate>2019</risdate><volume>31</volume><issue>3</issue><spage>211</spage><epage>218</epage><pages>211-218</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>In this study, a total of 10 bacterial strains were screened for their ability to reduce cyclohexyl(phenyl)methanone 1 to its corresponding alcohol. Among these strains, Lactobacillus paracasei BD101 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent L paracasei BD101, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of cyclohexyl(phenyl)methanone (1) by L paracasei BD101 gave (S)‐cyclohexyl(phenyl)methanol (2) with 92% yield and >99% enantiomeric excess. The preparative scale study was carried out, and a total of 5.602 g of (S)‐cyclohexyl(phenyl)methanol in high enantiomerically pure form (>99% enantiomeric excess) was produced. L paracasei BD101 has been shown to be an important biocatalyst in asymmetric reduction of bulky substrates. 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| ispartof | Chirality (New York, N.Y.), 2019-03, Vol.31 (3), p.211-218 |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alcohols asymmetric reduction biocatalyst Biocatalysts biotransformations chiral aryl methanols Enantiomers enantioselectivity Ketones Lactobacillus paracasei Methanol Reducing agents Reduction Strains (organisms) Substrates |
| title | Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)‐cyclohexyl(phenyl)methanol |
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