Water as Cosolvent: Nonviscous Deep Eutectic Solvents for Efficient Lipase‐Catalyzed Esterifications
The use of deep eutectic solvent (DES)/water mixtures were explored for the selective enzymatic synthesis of α‐monobenzoate glycerol (α‐MBG) from glycerol and benzoic acid as substrates. Experiments were performed with four DES, three of them containing choline chloride (ChCl), combined with urea (U...
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description | The use of deep eutectic solvent (DES)/water mixtures were explored for the selective enzymatic synthesis of α‐monobenzoate glycerol (α‐MBG) from glycerol and benzoic acid as substrates. Experiments were performed with four DES, three of them containing choline chloride (ChCl), combined with urea (URA), glycerol (GLY), and ethylene glycol (ETA) (in all cases ChCl/HBD 1:2 mol ratio), and another one formed with methylammonium chloride and glycerol (MA/GLY 1:3 mol ratio). The best conversions (99 %) were achieved with immobilized lipase B from Candida antarctica (CAL‐B) when ChCl/GLY was used as the solvent and the substrate at the same time. The use of water as a cosolvent (8 % v/v) led to a significant decrease in the viscosity of the DES, and full conversions were then reached. Reusability studies of the biocatalyst revealed a 37 % decrease in activity after the first batch, but the activity remained mostly constant for the rest of the cycles.
Skills acquisition by solvents: Blends of deep eutectic solvents and water lead to less viscous media that enable lipase‐catalyzed synthetic reactions and that dissolve substrates with different polarities. These blends show enzyme compatibility, retain their nonconventional nature, are nonviscous, and are excellent solubilizers for challenging substrates. |
doi_str_mv | 10.1002/cctc.201601575 |
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Skills acquisition by solvents: Blends of deep eutectic solvents and water lead to less viscous media that enable lipase‐catalyzed synthetic reactions and that dissolve substrates with different polarities. These blends show enzyme compatibility, retain their nonconventional nature, are nonviscous, and are excellent solubilizers for challenging substrates.</description><identifier>ISSN: 1867-3880</identifier><identifier>EISSN: 1867-3899</identifier><identifier>DOI: 10.1002/cctc.201601575</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>biocatalysis ; deep eutectic solvents ; enzymes ; esterification ; Glycerol ; solvent effects</subject><ispartof>ChemCatChem, 2017-04, Vol.9 (8), p.1393-1396</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3175-ef198f1ea2900ec41cc2d7f60327801f00fdccdaea62033fc117e863b29861a83</citedby><cites>FETCH-LOGICAL-c3175-ef198f1ea2900ec41cc2d7f60327801f00fdccdaea62033fc117e863b29861a83</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%2Fcctc.201601575$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcctc.201601575$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Guajardo, Nadia</creatorcontrib><creatorcontrib>Domínguez de María, Pablo</creatorcontrib><creatorcontrib>Ahumada, Katherine</creatorcontrib><creatorcontrib>Schrebler, Rodrigo A.</creatorcontrib><creatorcontrib>Ramírez‐Tagle, Rodrigo</creatorcontrib><creatorcontrib>Crespo, Fernando A.</creatorcontrib><creatorcontrib>Carlesi, Carlos</creatorcontrib><title>Water as Cosolvent: Nonviscous Deep Eutectic Solvents for Efficient Lipase‐Catalyzed Esterifications</title><title>ChemCatChem</title><description>The use of deep eutectic solvent (DES)/water mixtures were explored for the selective enzymatic synthesis of α‐monobenzoate glycerol (α‐MBG) from glycerol and benzoic acid as substrates. Experiments were performed with four DES, three of them containing choline chloride (ChCl), combined with urea (URA), glycerol (GLY), and ethylene glycol (ETA) (in all cases ChCl/HBD 1:2 mol ratio), and another one formed with methylammonium chloride and glycerol (MA/GLY 1:3 mol ratio). The best conversions (99 %) were achieved with immobilized lipase B from Candida antarctica (CAL‐B) when ChCl/GLY was used as the solvent and the substrate at the same time. The use of water as a cosolvent (8 % v/v) led to a significant decrease in the viscosity of the DES, and full conversions were then reached. Reusability studies of the biocatalyst revealed a 37 % decrease in activity after the first batch, but the activity remained mostly constant for the rest of the cycles.
Skills acquisition by solvents: Blends of deep eutectic solvents and water lead to less viscous media that enable lipase‐catalyzed synthetic reactions and that dissolve substrates with different polarities. These blends show enzyme compatibility, retain their nonconventional nature, are nonviscous, and are excellent solubilizers for challenging substrates.</description><subject>biocatalysis</subject><subject>deep eutectic solvents</subject><subject>enzymes</subject><subject>esterification</subject><subject>Glycerol</subject><subject>solvent effects</subject><issn>1867-3880</issn><issn>1867-3899</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkM1KxDAURoMoOI5uXQdcd7xppk3iTmr9gUEXjrgMMU0gQ21qk46MKx_BZ_RJ7FAZl67uvXC-78JB6JTAjACk51pHPUuB5EAylu2hCeE5SygXYn-3czhERyGsAHJBWTZB9llF02EVcOGDr9emiRf43jdrF7TvA74ypsVlH42OTuPHkQjY-g6X1jrthhMvXKuC-f78KlRU9ebDVLgMQ60bABWdb8IxOrCqDubkd07R03W5LG6TxcPNXXG5SDQlLEuMJYJbYlQqAIyeE63TitkcaMo4EAtgK60rZVSeAqVWE8IMz-lLKnhOFKdTdDb2tp1_602IcuX7rhleSsIFCDYXsKVmI6U7H0JnrGw796q6jSQgty7l1qXcuRwCYgy8u9ps_qFlUSyLv-wPDpN6jQ</recordid><startdate>20170421</startdate><enddate>20170421</enddate><creator>Guajardo, Nadia</creator><creator>Domínguez de María, Pablo</creator><creator>Ahumada, Katherine</creator><creator>Schrebler, Rodrigo A.</creator><creator>Ramírez‐Tagle, Rodrigo</creator><creator>Crespo, Fernando A.</creator><creator>Carlesi, Carlos</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20170421</creationdate><title>Water as Cosolvent: Nonviscous Deep Eutectic Solvents for Efficient Lipase‐Catalyzed Esterifications</title><author>Guajardo, Nadia ; Domínguez de María, Pablo ; Ahumada, Katherine ; Schrebler, Rodrigo A. ; Ramírez‐Tagle, Rodrigo ; Crespo, Fernando A. ; Carlesi, Carlos</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3175-ef198f1ea2900ec41cc2d7f60327801f00fdccdaea62033fc117e863b29861a83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>biocatalysis</topic><topic>deep eutectic solvents</topic><topic>enzymes</topic><topic>esterification</topic><topic>Glycerol</topic><topic>solvent effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guajardo, Nadia</creatorcontrib><creatorcontrib>Domínguez de María, Pablo</creatorcontrib><creatorcontrib>Ahumada, Katherine</creatorcontrib><creatorcontrib>Schrebler, Rodrigo A.</creatorcontrib><creatorcontrib>Ramírez‐Tagle, Rodrigo</creatorcontrib><creatorcontrib>Crespo, Fernando A.</creatorcontrib><creatorcontrib>Carlesi, Carlos</creatorcontrib><collection>CrossRef</collection><jtitle>ChemCatChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guajardo, Nadia</au><au>Domínguez de María, Pablo</au><au>Ahumada, Katherine</au><au>Schrebler, Rodrigo A.</au><au>Ramírez‐Tagle, Rodrigo</au><au>Crespo, Fernando A.</au><au>Carlesi, Carlos</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Water as Cosolvent: Nonviscous Deep Eutectic Solvents for Efficient Lipase‐Catalyzed Esterifications</atitle><jtitle>ChemCatChem</jtitle><date>2017-04-21</date><risdate>2017</risdate><volume>9</volume><issue>8</issue><spage>1393</spage><epage>1396</epage><pages>1393-1396</pages><issn>1867-3880</issn><eissn>1867-3899</eissn><abstract>The use of deep eutectic solvent (DES)/water mixtures were explored for the selective enzymatic synthesis of α‐monobenzoate glycerol (α‐MBG) from glycerol and benzoic acid as substrates. Experiments were performed with four DES, three of them containing choline chloride (ChCl), combined with urea (URA), glycerol (GLY), and ethylene glycol (ETA) (in all cases ChCl/HBD 1:2 mol ratio), and another one formed with methylammonium chloride and glycerol (MA/GLY 1:3 mol ratio). The best conversions (99 %) were achieved with immobilized lipase B from Candida antarctica (CAL‐B) when ChCl/GLY was used as the solvent and the substrate at the same time. The use of water as a cosolvent (8 % v/v) led to a significant decrease in the viscosity of the DES, and full conversions were then reached. Reusability studies of the biocatalyst revealed a 37 % decrease in activity after the first batch, but the activity remained mostly constant for the rest of the cycles.
Skills acquisition by solvents: Blends of deep eutectic solvents and water lead to less viscous media that enable lipase‐catalyzed synthetic reactions and that dissolve substrates with different polarities. These blends show enzyme compatibility, retain their nonconventional nature, are nonviscous, and are excellent solubilizers for challenging substrates.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/cctc.201601575</doi><tpages>4</tpages></addata></record> |
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subjects | biocatalysis deep eutectic solvents enzymes esterification Glycerol solvent effects |
title | Water as Cosolvent: Nonviscous Deep Eutectic Solvents for Efficient Lipase‐Catalyzed Esterifications |
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