Synthesis of ethyl (R)-4-chloro-3-hydroxybutyrate by immobilized cells using amino acid-modified magnetic nanoparticles
[Display omitted] •Ethyl (R)-4-chloro-3-hydroxybutyrate was synthesized by Fe3O4-Arg-Cells.•Arginine is a desirable chemical as ligand anchored with magnetic nanoparticles.•Fe3O4-Arg-Cells like microscopic stirrers in an alternating magnetic field.•Continuous reaction in magnetic fluidized bed react...
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Veröffentlicht in: | Process biochemistry (1991) 2020-12, Vol.99, p.9-20 |
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container_title | Process biochemistry (1991) |
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creator | Lu, Yuan Dai, Hongqian Shi, Hanbing Tang, Lan Sun, Xingyuan Ou, Zhimin |
description | [Display omitted]
•Ethyl (R)-4-chloro-3-hydroxybutyrate was synthesized by Fe3O4-Arg-Cells.•Arginine is a desirable chemical as ligand anchored with magnetic nanoparticles.•Fe3O4-Arg-Cells like microscopic stirrers in an alternating magnetic field.•Continuous reaction in magnetic fluidized bed reactor improved catalyst efficiency.
Fe3O4-Arg was selected as the optimal carrier due to its high activity recovery of immobilized cells in the preparation of Fe3O4-Arg-Cells. The optimal immobilization conditions for the preparation of Fe3O4-Arg-Cells were 30 °C, 4 h, pH 7, and 3 g dry yeast. The activity recovery of immobilized cells reached 76.8 %. For a batch reduction in a shaker in an alternating magnetic field, Fe3O4-Arg-Cells were used as a catalyst to gain ethyl (R)-4-chloro-3-hydroxybutyrate ((R)-CHBE). For further improvement in reduction productivity, a continuous reduction in the magnetic fluidized bed reactor system (MFBRS) was completed. Under their optimal transformation conditions, it took 24 h for Fe3O4-Arg-Cells to complete the conversion of ethyl 4-chloro-3-oxobutanoate (COBE) (0.8553 mol/L) in the shaker and only 8 h for the batch reduction in an alternating magnetic field. Continuous reduction in MFBRS provided new ideas for the efficient production of (R)-CHBE; 1.5882 mol/L (10 mL) of COBE can be completely converted in 6 h. The conversion and enantiomeric excess (e.e.) of (R)-CHBE were 100 % and above 99.9 % respectively, in the three reaction systems mentioned above. |
doi_str_mv | 10.1016/j.procbio.2020.07.027 |
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•Ethyl (R)-4-chloro-3-hydroxybutyrate was synthesized by Fe3O4-Arg-Cells.•Arginine is a desirable chemical as ligand anchored with magnetic nanoparticles.•Fe3O4-Arg-Cells like microscopic stirrers in an alternating magnetic field.•Continuous reaction in magnetic fluidized bed reactor improved catalyst efficiency.
Fe3O4-Arg was selected as the optimal carrier due to its high activity recovery of immobilized cells in the preparation of Fe3O4-Arg-Cells. The optimal immobilization conditions for the preparation of Fe3O4-Arg-Cells were 30 °C, 4 h, pH 7, and 3 g dry yeast. The activity recovery of immobilized cells reached 76.8 %. For a batch reduction in a shaker in an alternating magnetic field, Fe3O4-Arg-Cells were used as a catalyst to gain ethyl (R)-4-chloro-3-hydroxybutyrate ((R)-CHBE). For further improvement in reduction productivity, a continuous reduction in the magnetic fluidized bed reactor system (MFBRS) was completed. Under their optimal transformation conditions, it took 24 h for Fe3O4-Arg-Cells to complete the conversion of ethyl 4-chloro-3-oxobutanoate (COBE) (0.8553 mol/L) in the shaker and only 8 h for the batch reduction in an alternating magnetic field. Continuous reduction in MFBRS provided new ideas for the efficient production of (R)-CHBE; 1.5882 mol/L (10 mL) of COBE can be completely converted in 6 h. The conversion and enantiomeric excess (e.e.) of (R)-CHBE were 100 % and above 99.9 % respectively, in the three reaction systems mentioned above.</description><identifier>ISSN: 1359-5113</identifier><identifier>EISSN: 1873-3298</identifier><identifier>DOI: 10.1016/j.procbio.2020.07.027</identifier><language>eng</language><publisher>Barking: Elsevier Ltd</publisher><subject>Alternating magnetic field ; Amino acid-modified magnetic nanoparticles ; Amino acids ; Asym-metric reduction ; biochemistry ; Catalysts ; Conversion ; Ethyl (R)-4-chloro-3-hydroxybutyrate ; Fluidized bed reactors ; Fluidized beds ; Immobilization ; Immobilized cells ; Iron oxides ; Magnetic fields ; Nanoparticles ; Recovery ; Reduction ; Yeasts</subject><ispartof>Process biochemistry (1991), 2020-12, Vol.99, p.9-20</ispartof><rights>2020 Elsevier Ltd</rights><rights>Copyright Elsevier BV Dec 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c370t-633e0e3be45f4ffe3b9f3807f6b5ea67e86b64dfdebeeaaee635e2738a64ba3f3</citedby><cites>FETCH-LOGICAL-c370t-633e0e3be45f4ffe3b9f3807f6b5ea67e86b64dfdebeeaaee635e2738a64ba3f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.procbio.2020.07.027$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids></links><search><creatorcontrib>Lu, Yuan</creatorcontrib><creatorcontrib>Dai, Hongqian</creatorcontrib><creatorcontrib>Shi, Hanbing</creatorcontrib><creatorcontrib>Tang, Lan</creatorcontrib><creatorcontrib>Sun, Xingyuan</creatorcontrib><creatorcontrib>Ou, Zhimin</creatorcontrib><title>Synthesis of ethyl (R)-4-chloro-3-hydroxybutyrate by immobilized cells using amino acid-modified magnetic nanoparticles</title><title>Process biochemistry (1991)</title><description>[Display omitted]
•Ethyl (R)-4-chloro-3-hydroxybutyrate was synthesized by Fe3O4-Arg-Cells.•Arginine is a desirable chemical as ligand anchored with magnetic nanoparticles.•Fe3O4-Arg-Cells like microscopic stirrers in an alternating magnetic field.•Continuous reaction in magnetic fluidized bed reactor improved catalyst efficiency.
Fe3O4-Arg was selected as the optimal carrier due to its high activity recovery of immobilized cells in the preparation of Fe3O4-Arg-Cells. The optimal immobilization conditions for the preparation of Fe3O4-Arg-Cells were 30 °C, 4 h, pH 7, and 3 g dry yeast. The activity recovery of immobilized cells reached 76.8 %. For a batch reduction in a shaker in an alternating magnetic field, Fe3O4-Arg-Cells were used as a catalyst to gain ethyl (R)-4-chloro-3-hydroxybutyrate ((R)-CHBE). For further improvement in reduction productivity, a continuous reduction in the magnetic fluidized bed reactor system (MFBRS) was completed. Under their optimal transformation conditions, it took 24 h for Fe3O4-Arg-Cells to complete the conversion of ethyl 4-chloro-3-oxobutanoate (COBE) (0.8553 mol/L) in the shaker and only 8 h for the batch reduction in an alternating magnetic field. Continuous reduction in MFBRS provided new ideas for the efficient production of (R)-CHBE; 1.5882 mol/L (10 mL) of COBE can be completely converted in 6 h. The conversion and enantiomeric excess (e.e.) of (R)-CHBE were 100 % and above 99.9 % respectively, in the three reaction systems mentioned above.</description><subject>Alternating magnetic field</subject><subject>Amino acid-modified magnetic nanoparticles</subject><subject>Amino acids</subject><subject>Asym-metric reduction</subject><subject>biochemistry</subject><subject>Catalysts</subject><subject>Conversion</subject><subject>Ethyl (R)-4-chloro-3-hydroxybutyrate</subject><subject>Fluidized bed reactors</subject><subject>Fluidized beds</subject><subject>Immobilization</subject><subject>Immobilized cells</subject><subject>Iron oxides</subject><subject>Magnetic fields</subject><subject>Nanoparticles</subject><subject>Recovery</subject><subject>Reduction</subject><subject>Yeasts</subject><issn>1359-5113</issn><issn>1873-3298</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFUU2LFDEUbETBdfUnCAEv6yFtPrqTnpPIsroLC4If55CkX3be0J2MSbfa_nozzJ68eHoFr6p4r6ppXnPWcsbVu0N7zMk7TK1ggrVMt0zoJ80FH7SkUuyGpxXLfkd7zuXz5kUpB8Yk55xdNL--bnHZQ8FCUiCw7LeJXH15Szvq91PKiUq638acfm9uXbZsFyBuIzjPyeGEf2AkHqapkLVgfCB2xpiI9TjSOY0YsO5n-xBhQU-ijeloc4UTlJfNs2CnAq8e52Xz_ePNt-tbev_50931h3vqpWYLVVICA-mg60MXQkW7IAemg3I9WKVhUE51YxjBAVgLoGQPQsvBqs5ZGeRlc3X2rRH9WKEsZsZyOtlGSGsxotddjUJ3vFLf_EM9pDXHep0RnR5Er7Q4sfozy-dUSoZgjhlnmzfDmTnVYQ7msQ5zqsMwbWodVff-rIP67U-EbIpHiB5GzOAXMyb8j8NfOu-Yyg</recordid><startdate>202012</startdate><enddate>202012</enddate><creator>Lu, Yuan</creator><creator>Dai, Hongqian</creator><creator>Shi, Hanbing</creator><creator>Tang, Lan</creator><creator>Sun, Xingyuan</creator><creator>Ou, Zhimin</creator><general>Elsevier Ltd</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>202012</creationdate><title>Synthesis of ethyl (R)-4-chloro-3-hydroxybutyrate by immobilized cells using amino acid-modified magnetic nanoparticles</title><author>Lu, Yuan ; Dai, Hongqian ; Shi, Hanbing ; Tang, Lan ; Sun, Xingyuan ; Ou, Zhimin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c370t-633e0e3be45f4ffe3b9f3807f6b5ea67e86b64dfdebeeaaee635e2738a64ba3f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alternating magnetic field</topic><topic>Amino acid-modified magnetic nanoparticles</topic><topic>Amino acids</topic><topic>Asym-metric reduction</topic><topic>biochemistry</topic><topic>Catalysts</topic><topic>Conversion</topic><topic>Ethyl (R)-4-chloro-3-hydroxybutyrate</topic><topic>Fluidized bed reactors</topic><topic>Fluidized beds</topic><topic>Immobilization</topic><topic>Immobilized cells</topic><topic>Iron oxides</topic><topic>Magnetic fields</topic><topic>Nanoparticles</topic><topic>Recovery</topic><topic>Reduction</topic><topic>Yeasts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lu, Yuan</creatorcontrib><creatorcontrib>Dai, Hongqian</creatorcontrib><creatorcontrib>Shi, Hanbing</creatorcontrib><creatorcontrib>Tang, Lan</creatorcontrib><creatorcontrib>Sun, Xingyuan</creatorcontrib><creatorcontrib>Ou, Zhimin</creatorcontrib><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</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>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Process biochemistry (1991)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lu, Yuan</au><au>Dai, Hongqian</au><au>Shi, Hanbing</au><au>Tang, Lan</au><au>Sun, Xingyuan</au><au>Ou, Zhimin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of ethyl (R)-4-chloro-3-hydroxybutyrate by immobilized cells using amino acid-modified magnetic nanoparticles</atitle><jtitle>Process biochemistry (1991)</jtitle><date>2020-12</date><risdate>2020</risdate><volume>99</volume><spage>9</spage><epage>20</epage><pages>9-20</pages><issn>1359-5113</issn><eissn>1873-3298</eissn><abstract>[Display omitted]
•Ethyl (R)-4-chloro-3-hydroxybutyrate was synthesized by Fe3O4-Arg-Cells.•Arginine is a desirable chemical as ligand anchored with magnetic nanoparticles.•Fe3O4-Arg-Cells like microscopic stirrers in an alternating magnetic field.•Continuous reaction in magnetic fluidized bed reactor improved catalyst efficiency.
Fe3O4-Arg was selected as the optimal carrier due to its high activity recovery of immobilized cells in the preparation of Fe3O4-Arg-Cells. The optimal immobilization conditions for the preparation of Fe3O4-Arg-Cells were 30 °C, 4 h, pH 7, and 3 g dry yeast. The activity recovery of immobilized cells reached 76.8 %. For a batch reduction in a shaker in an alternating magnetic field, Fe3O4-Arg-Cells were used as a catalyst to gain ethyl (R)-4-chloro-3-hydroxybutyrate ((R)-CHBE). For further improvement in reduction productivity, a continuous reduction in the magnetic fluidized bed reactor system (MFBRS) was completed. Under their optimal transformation conditions, it took 24 h for Fe3O4-Arg-Cells to complete the conversion of ethyl 4-chloro-3-oxobutanoate (COBE) (0.8553 mol/L) in the shaker and only 8 h for the batch reduction in an alternating magnetic field. Continuous reduction in MFBRS provided new ideas for the efficient production of (R)-CHBE; 1.5882 mol/L (10 mL) of COBE can be completely converted in 6 h. The conversion and enantiomeric excess (e.e.) of (R)-CHBE were 100 % and above 99.9 % respectively, in the three reaction systems mentioned above.</abstract><cop>Barking</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.procbio.2020.07.027</doi><tpages>12</tpages></addata></record> |
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subjects | Alternating magnetic field Amino acid-modified magnetic nanoparticles Amino acids Asym-metric reduction biochemistry Catalysts Conversion Ethyl (R)-4-chloro-3-hydroxybutyrate Fluidized bed reactors Fluidized beds Immobilization Immobilized cells Iron oxides Magnetic fields Nanoparticles Recovery Reduction Yeasts |
title | Synthesis of ethyl (R)-4-chloro-3-hydroxybutyrate by immobilized cells using amino acid-modified magnetic nanoparticles |
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