Evaluation of Pseudoenantiomeric Mixed Carbonates as Efficient Fluorogenic Probes for Enantioselectivity Screening
We report mixed carbonates as enzyme substrates and demonstrate their application as fluorogenic probes for lipase and esterase enantiopreference screening. By the application of pseudoenantiomers with distinct fluorescence behaviors, it is possible to evaluate the activity and enantiopreference of...
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| Veröffentlicht in: | Chembiochem : a European journal of chemical biology 2016-01, Vol.17 (1), p.71-76 |
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| container_title | Chembiochem : a European journal of chemical biology |
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| creator | Zadlo, Anna Koszelewski, Dominik Borys, Filip Ostaszewski, Ryszard |
| description | We report mixed carbonates as enzyme substrates and demonstrate their application as fluorogenic probes for lipase and esterase enantiopreference screening. By the application of pseudoenantiomers with distinct fluorescence behaviors, it is possible to evaluate the activity and enantiopreference of hydrolytic enzymes. In order to validate our method, enantioselectivities calculated from fluorometric measurements were compared with the results obtained from larger‐scale kinetic resolution.
Pseudoenantiomeric mixed carbonates with distinct fluorogenic properties are shown to be very useful probes for screening lipase and esterase enantioselectivity. The simultaneous use of pseudoenantiomeric substrates overcomes conventional assays with single enantiomer substrates, as the effects of competitive binding are taken into account. |
| doi_str_mv | 10.1002/cbic.201500509 |
| format | Article |
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Pseudoenantiomeric mixed carbonates with distinct fluorogenic properties are shown to be very useful probes for screening lipase and esterase enantioselectivity. The simultaneous use of pseudoenantiomeric substrates overcomes conventional assays with single enantiomer substrates, as the effects of competitive binding are taken into account.</description><identifier>ISSN: 1439-4227</identifier><identifier>EISSN: 1439-7633</identifier><identifier>DOI: 10.1002/cbic.201500509</identifier><identifier>PMID: 26507370</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Carbonates - chemistry ; enantioselectivity ; Esterases - chemistry ; Esterases - metabolism ; Fluorescence ; Fluorescent Dyes - chemistry ; fluorescent probes ; fluorogenic assay ; high-throughput screening ; Lipase - chemistry ; Lipase - metabolism ; pseudoenantiomers ; Spectrometry, Fluorescence ; Stereoisomerism</subject><ispartof>Chembiochem : a European journal of chemical biology, 2016-01, Vol.17 (1), p.71-76</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5189-9d80e6767cd409d0b1f2984a45c9d1f9583d2ba8911df9d15b7a727b02a7049f3</citedby><cites>FETCH-LOGICAL-c5189-9d80e6767cd409d0b1f2984a45c9d1f9583d2ba8911df9d15b7a727b02a7049f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbic.201500509$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbic.201500509$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27915,27916,45565,45566</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26507370$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zadlo, Anna</creatorcontrib><creatorcontrib>Koszelewski, Dominik</creatorcontrib><creatorcontrib>Borys, Filip</creatorcontrib><creatorcontrib>Ostaszewski, Ryszard</creatorcontrib><title>Evaluation of Pseudoenantiomeric Mixed Carbonates as Efficient Fluorogenic Probes for Enantioselectivity Screening</title><title>Chembiochem : a European journal of chemical biology</title><addtitle>ChemBioChem</addtitle><description>We report mixed carbonates as enzyme substrates and demonstrate their application as fluorogenic probes for lipase and esterase enantiopreference screening. By the application of pseudoenantiomers with distinct fluorescence behaviors, it is possible to evaluate the activity and enantiopreference of hydrolytic enzymes. In order to validate our method, enantioselectivities calculated from fluorometric measurements were compared with the results obtained from larger‐scale kinetic resolution.
Pseudoenantiomeric mixed carbonates with distinct fluorogenic properties are shown to be very useful probes for screening lipase and esterase enantioselectivity. The simultaneous use of pseudoenantiomeric substrates overcomes conventional assays with single enantiomer substrates, as the effects of competitive binding are taken into account.</description><subject>Carbonates - chemistry</subject><subject>enantioselectivity</subject><subject>Esterases - chemistry</subject><subject>Esterases - metabolism</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemistry</subject><subject>fluorescent probes</subject><subject>fluorogenic assay</subject><subject>high-throughput screening</subject><subject>Lipase - chemistry</subject><subject>Lipase - metabolism</subject><subject>pseudoenantiomers</subject><subject>Spectrometry, Fluorescence</subject><subject>Stereoisomerism</subject><issn>1439-4227</issn><issn>1439-7633</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1v1DAURSMEoqWwZYkssWGTwR-xHS9pNFOKCkSiiKXlOM-VSyZu7aR0_j0eZRghNqxsPZ979ORbFK8JXhGM6XvbebuimHCMOVZPilNSMVVKwdjTw72iVJ4UL1K6xRgrwcjz4oQKjiWT-LSI6wczzGbyYUTBoTbB3AcYzZgnW4jeos_-EXrUmNiF0UyQkElo7Zy3HsYJbYY5xHADYybbGLr87kJE68WQYAA7-Qc_7dA3GyFj483L4pkzQ4JXh_Os-L5ZXzcfy6uvF5fNh6vSclKrUvU1BiGFtH2FVY874qiqK1Nxq3riFK9ZTztTK0J6lye8k0ZS2WFqJK6UY2fFu8V7F8P9DGnSW58sDIMZIcxJE8krTikTNKNv_0FvwxzHvN2eYhliQmRqtVA2hpQiOH0X_dbEnSZY79vQ-zb0sY0ceHPQzt0W-iP-5_szoBbglx9g9x-dbs4vm7_l5ZL1aYLHY9bEn1pkOdc_vlzoT7Q9bzf8WrfsN_vxpi8</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Zadlo, Anna</creator><creator>Koszelewski, Dominik</creator><creator>Borys, Filip</creator><creator>Ostaszewski, Ryszard</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7QL</scope><scope>7QO</scope><scope>7TM</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20160101</creationdate><title>Evaluation of Pseudoenantiomeric Mixed Carbonates as Efficient Fluorogenic Probes for Enantioselectivity Screening</title><author>Zadlo, Anna ; Koszelewski, Dominik ; Borys, Filip ; Ostaszewski, Ryszard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5189-9d80e6767cd409d0b1f2984a45c9d1f9583d2ba8911df9d15b7a727b02a7049f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Carbonates - chemistry</topic><topic>enantioselectivity</topic><topic>Esterases - chemistry</topic><topic>Esterases - metabolism</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemistry</topic><topic>fluorescent probes</topic><topic>fluorogenic assay</topic><topic>high-throughput screening</topic><topic>Lipase - chemistry</topic><topic>Lipase - metabolism</topic><topic>pseudoenantiomers</topic><topic>Spectrometry, Fluorescence</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zadlo, Anna</creatorcontrib><creatorcontrib>Koszelewski, Dominik</creatorcontrib><creatorcontrib>Borys, Filip</creatorcontrib><creatorcontrib>Ostaszewski, Ryszard</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chembiochem : a European journal of chemical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zadlo, Anna</au><au>Koszelewski, Dominik</au><au>Borys, Filip</au><au>Ostaszewski, Ryszard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Evaluation of Pseudoenantiomeric Mixed Carbonates as Efficient Fluorogenic Probes for Enantioselectivity Screening</atitle><jtitle>Chembiochem : a European journal of chemical biology</jtitle><addtitle>ChemBioChem</addtitle><date>2016-01-01</date><risdate>2016</risdate><volume>17</volume><issue>1</issue><spage>71</spage><epage>76</epage><pages>71-76</pages><issn>1439-4227</issn><eissn>1439-7633</eissn><abstract>We report mixed carbonates as enzyme substrates and demonstrate their application as fluorogenic probes for lipase and esterase enantiopreference screening. By the application of pseudoenantiomers with distinct fluorescence behaviors, it is possible to evaluate the activity and enantiopreference of hydrolytic enzymes. In order to validate our method, enantioselectivities calculated from fluorometric measurements were compared with the results obtained from larger‐scale kinetic resolution.
Pseudoenantiomeric mixed carbonates with distinct fluorogenic properties are shown to be very useful probes for screening lipase and esterase enantioselectivity. The simultaneous use of pseudoenantiomeric substrates overcomes conventional assays with single enantiomer substrates, as the effects of competitive binding are taken into account.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26507370</pmid><doi>10.1002/cbic.201500509</doi><tpages>6</tpages></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Carbonates - chemistry enantioselectivity Esterases - chemistry Esterases - metabolism Fluorescence Fluorescent Dyes - chemistry fluorescent probes fluorogenic assay high-throughput screening Lipase - chemistry Lipase - metabolism pseudoenantiomers Spectrometry, Fluorescence Stereoisomerism |
| title | Evaluation of Pseudoenantiomeric Mixed Carbonates as Efficient Fluorogenic Probes for Enantioselectivity Screening |
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