Effects of hydrolysis and esterification side-reactions on the kinetic resolution of enzyme-catalyzed irreversible transesterification in organic solvents
A simplified kinetic model for the enzyme-catalyzed irreversible transesterification in organic solvents was proposed by considering the hydrolysis and esterification side reactions. The analysis was extended to the kinetic resolution of activated racemic esters containing a chiral center in the aci...
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| Veröffentlicht in: | Chemical engineering science 2000-10, Vol.55 (20), p.4571-4582 |
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| creator | Tsai, S.W. Cheng, I.C. Huang, C.M. |
| description | A simplified kinetic model for the enzyme-catalyzed irreversible transesterification in organic solvents was proposed by considering the hydrolysis and esterification side reactions. The analysis was extended to the kinetic resolution of activated racemic esters containing a chiral center in the acid moiety, and was confirmed from the lipase-catalyzed enantioselective transesterification between (R,S)-suprofen 2,2,2-trifluoroethyl ester and 2-
N-morpholinoethanol (or di(ethylene glycol)) in cyclohexane. Theoretical analysis indicates that the time-course yield and/or the enantiomeric excess for the desired (S)-ester product may be improved if the employed enzyme has a higher activity and/or enantioselectivity for the hydrolysis and esterification than the transesterification. |
| doi_str_mv | 10.1016/S0009-2509(00)00093-2 |
| format | Article |
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N-morpholinoethanol (or di(ethylene glycol)) in cyclohexane. Theoretical analysis indicates that the time-course yield and/or the enantiomeric excess for the desired (S)-ester product may be improved if the employed enzyme has a higher activity and/or enantioselectivity for the hydrolysis and esterification than the transesterification.</description><identifier>ISSN: 0009-2509</identifier><identifier>EISSN: 1873-4405</identifier><identifier>DOI: 10.1016/S0009-2509(00)00093-2</identifier><identifier>CODEN: CESCAC</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Catalysis ; Composition effects ; Esterification ; Esters ; Fundamental and applied biological sciences. Psychology ; Hydrolysis ; Irreversible transesterification ; Kinetic resolution ; Lipase ; Methods. Procedures. Technologies ; Organic solvents ; Suprofen esters</subject><ispartof>Chemical engineering science, 2000-10, Vol.55 (20), p.4571-4582</ispartof><rights>2000 Elsevier Science B.V.</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c366t-f0d6fde6678fec9264a9cd5f21a0073d54de61e0d823fcc95ae4f9b525ded6443</citedby><cites>FETCH-LOGICAL-c366t-f0d6fde6678fec9264a9cd5f21a0073d54de61e0d823fcc95ae4f9b525ded6443</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0009250900000932$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=788681$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Tsai, S.W.</creatorcontrib><creatorcontrib>Cheng, I.C.</creatorcontrib><creatorcontrib>Huang, C.M.</creatorcontrib><title>Effects of hydrolysis and esterification side-reactions on the kinetic resolution of enzyme-catalyzed irreversible transesterification in organic solvents</title><title>Chemical engineering science</title><description>A simplified kinetic model for the enzyme-catalyzed irreversible transesterification in organic solvents was proposed by considering the hydrolysis and esterification side reactions. The analysis was extended to the kinetic resolution of activated racemic esters containing a chiral center in the acid moiety, and was confirmed from the lipase-catalyzed enantioselective transesterification between (R,S)-suprofen 2,2,2-trifluoroethyl ester and 2-
N-morpholinoethanol (or di(ethylene glycol)) in cyclohexane. Theoretical analysis indicates that the time-course yield and/or the enantiomeric excess for the desired (S)-ester product may be improved if the employed enzyme has a higher activity and/or enantioselectivity for the hydrolysis and esterification than the transesterification.</description><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Catalysis</subject><subject>Composition effects</subject><subject>Esterification</subject><subject>Esters</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrolysis</subject><subject>Irreversible transesterification</subject><subject>Kinetic resolution</subject><subject>Lipase</subject><subject>Methods. Procedures. Technologies</subject><subject>Organic solvents</subject><subject>Suprofen esters</subject><issn>0009-2509</issn><issn>1873-4405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNqFkU-LFDEQxYMoOK5-BCEgiB5ak-4k3X0SWdY_sOBBPYdsUnFLe9Jrqmeg96P4aa2ZWfbgxVMo8nuv8vKEeK7VG620e_tVKTU2rVXjK6VeH4auaR-IjR76rjFG2Ydic488Fk-IfvLY91ptxJ-LnCEuJOcsr9dU52klJBlKkkALVMwYw4JzkYQJmgohHibmi1yuQf7CAgtGWYHmaXcE2QnK7bqFhpVhWm8hSawV9lAJryaQSw2F_nFH1tUfobAVG-2hLPRUPMphInh2d56J7x8uvp1_ai6_fPx8_v6yiZ1zS5NVcjmBc_3AScbWmTDGZHOrA4fskjV8qUGloe1yjKMNYPJ4ZVubIDljujPx8uR7U-ffO36X3yJFmKZQYN6Rb7Uxths6Bu0JjHUmqpD9TcVtqKvXyh-a8Mcm_OGbvVL-2IRvWffibkGgGKbM8SPSvbgfBjdopt6dKOCse4TqKSKUCAkrN-TTjP_Z8xdp16Ki</recordid><startdate>20001001</startdate><enddate>20001001</enddate><creator>Tsai, S.W.</creator><creator>Cheng, I.C.</creator><creator>Huang, C.M.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20001001</creationdate><title>Effects of hydrolysis and esterification side-reactions on the kinetic resolution of enzyme-catalyzed irreversible transesterification in organic solvents</title><author>Tsai, S.W. ; Cheng, I.C. ; Huang, C.M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c366t-f0d6fde6678fec9264a9cd5f21a0073d54de61e0d823fcc95ae4f9b525ded6443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Catalysis</topic><topic>Composition effects</topic><topic>Esterification</topic><topic>Esters</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrolysis</topic><topic>Irreversible transesterification</topic><topic>Kinetic resolution</topic><topic>Lipase</topic><topic>Methods. Procedures. Technologies</topic><topic>Organic solvents</topic><topic>Suprofen esters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tsai, S.W.</creatorcontrib><creatorcontrib>Cheng, I.C.</creatorcontrib><creatorcontrib>Huang, C.M.</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Chemical engineering science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tsai, S.W.</au><au>Cheng, I.C.</au><au>Huang, C.M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effects of hydrolysis and esterification side-reactions on the kinetic resolution of enzyme-catalyzed irreversible transesterification in organic solvents</atitle><jtitle>Chemical engineering science</jtitle><date>2000-10-01</date><risdate>2000</risdate><volume>55</volume><issue>20</issue><spage>4571</spage><epage>4582</epage><pages>4571-4582</pages><issn>0009-2509</issn><eissn>1873-4405</eissn><coden>CESCAC</coden><abstract>A simplified kinetic model for the enzyme-catalyzed irreversible transesterification in organic solvents was proposed by considering the hydrolysis and esterification side reactions. The analysis was extended to the kinetic resolution of activated racemic esters containing a chiral center in the acid moiety, and was confirmed from the lipase-catalyzed enantioselective transesterification between (R,S)-suprofen 2,2,2-trifluoroethyl ester and 2-
N-morpholinoethanol (or di(ethylene glycol)) in cyclohexane. Theoretical analysis indicates that the time-course yield and/or the enantiomeric excess for the desired (S)-ester product may be improved if the employed enzyme has a higher activity and/or enantioselectivity for the hydrolysis and esterification than the transesterification.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><doi>10.1016/S0009-2509(00)00093-2</doi><tpages>12</tpages></addata></record> |
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| ispartof | Chemical engineering science, 2000-10, Vol.55 (20), p.4571-4582 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Catalysis Composition effects Esterification Esters Fundamental and applied biological sciences. Psychology Hydrolysis Irreversible transesterification Kinetic resolution Lipase Methods. Procedures. Technologies Organic solvents Suprofen esters |
| title | Effects of hydrolysis and esterification side-reactions on the kinetic resolution of enzyme-catalyzed irreversible transesterification in organic solvents |
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