Chemo-enzymatic synthesis of both enantiomers of the anti-anginal drug ranolazine
Both enantiomers of the potential anti-anginal drug ranolazine have been synthesized from enantiopure (R)- and (S)-3-chloro-1-(2-methoxyphenoxy)propan-2-ol. These chiral building blocks were produced by kinetic resolution of the corresponding racemic butanoate by hydrolysis catalyzed by immobilized...
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| Veröffentlicht in: | Biocatalysis and biotransformation 2005-01, Vol.23 (1), p.45-51 |
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| container_title | Biocatalysis and biotransformation |
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| creator | Riise Moen, Anders Karstad, Rasmus Anthonsen, Thorleif |
| description | Both enantiomers of the potential anti-anginal drug ranolazine have been synthesized from enantiopure (R)- and (S)-3-chloro-1-(2-methoxyphenoxy)propan-2-ol. These chiral building blocks were produced by kinetic resolution of the corresponding racemic butanoate by hydrolysis catalyzed by immobilized lipase from Rhizomucor miehei (Lipozym RM IM) or lipase B from Candida antarctica (Novozym 435). (R)-3-Chloro-1-(2-methoxyphenoxy)propan-2-ol was also made from the racemate in high yield and ee in a stereoinversion reaction. |
| doi_str_mv | 10.1080/10242420500067357 |
| format | Article |
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These chiral building blocks were produced by kinetic resolution of the corresponding racemic butanoate by hydrolysis catalyzed by immobilized lipase from Rhizomucor miehei (Lipozym RM IM) or lipase B from Candida antarctica (Novozym 435). (R)-3-Chloro-1-(2-methoxyphenoxy)propan-2-ol was also made from the racemate in high yield and ee in a stereoinversion reaction.</description><identifier>ISSN: 1024-2422</identifier><identifier>EISSN: 1029-2446</identifier><identifier>DOI: 10.1080/10242420500067357</identifier><language>eng</language><publisher>Abingdon: Informa UK Ltd</publisher><subject>Angina ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Candida antarctica ; capillary electrophoresis ; chiral analysis ; Fundamental and applied biological sciences. Psychology ; highly sulfated cyklodextrins ; kinetic resolution ; Methods. Procedures. 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These chiral building blocks were produced by kinetic resolution of the corresponding racemic butanoate by hydrolysis catalyzed by immobilized lipase from Rhizomucor miehei (Lipozym RM IM) or lipase B from Candida antarctica (Novozym 435). (R)-3-Chloro-1-(2-methoxyphenoxy)propan-2-ol was also made from the racemate in high yield and ee in a stereoinversion reaction.</description><subject>Angina</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Candida antarctica</subject><subject>capillary electrophoresis</subject><subject>chiral analysis</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>highly sulfated cyklodextrins</subject><subject>kinetic resolution</subject><subject>Methods. Procedures. Technologies</subject><subject>ranexa</subject><subject>ranolazine</subject><subject>Rhizomucor miehei</subject><subject>stereoinversion</subject><issn>1024-2422</issn><issn>1029-2446</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNp9UE1LxDAQLaLg5w_w1oveqpM2bVP0IotfsCCCnss0O7GRNFmTLrL-erPuioggc5jhzXvz8ZLkmMEZAwHnDHIeA0oAqOqirLeSvYg1Wc55tf1V81jn-W6yH8IrACvypt5LHic9DS4j-7EccNQyDUs79hR0SJ1KOzf2KVm0o3YD-S8sdtMVkKF90RZNOvOLl9SjdQY_tKXDZEehCXS0yQfJ88310-Qumz7c3k-uppnkXIxZTQKlFB2nGQlOoBR1sixVIzHHQjBAJkqaSSGhoqJRrISSqbwrpKKqU01xkJyu5869e1tQGNtBB0nGoCW3CC2rSyhA8Ehka6L0LgRPqp17PaBftgzalXntH_Oi5mQzHINEo-J7UocfYVU1NTAWeZdrnrbK-QHfnTezdsSlcf5bVPy35uKXvCc0Yy_RU_vqFj66G_458hPERJWg</recordid><startdate>20050101</startdate><enddate>20050101</enddate><creator>Riise Moen, Anders</creator><creator>Karstad, Rasmus</creator><creator>Anthonsen, Thorleif</creator><general>Informa UK Ltd</general><general>Taylor & Francis</general><general>Taylor and Francis</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20050101</creationdate><title>Chemo-enzymatic synthesis of both enantiomers of the anti-anginal drug ranolazine</title><author>Riise Moen, Anders ; Karstad, Rasmus ; Anthonsen, Thorleif</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c448t-7e8acc8b4ede84e0ffebc55f9ca2a3810a185edc8c06e39f15051f2b3cfe6bf93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Angina</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Candida antarctica</topic><topic>capillary electrophoresis</topic><topic>chiral analysis</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>highly sulfated cyklodextrins</topic><topic>kinetic resolution</topic><topic>Methods. Procedures. Technologies</topic><topic>ranexa</topic><topic>ranolazine</topic><topic>Rhizomucor miehei</topic><topic>stereoinversion</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Riise Moen, Anders</creatorcontrib><creatorcontrib>Karstad, Rasmus</creatorcontrib><creatorcontrib>Anthonsen, Thorleif</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Biocatalysis and biotransformation</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Riise Moen, Anders</au><au>Karstad, Rasmus</au><au>Anthonsen, Thorleif</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemo-enzymatic synthesis of both enantiomers of the anti-anginal drug ranolazine</atitle><jtitle>Biocatalysis and biotransformation</jtitle><date>2005-01-01</date><risdate>2005</risdate><volume>23</volume><issue>1</issue><spage>45</spage><epage>51</epage><pages>45-51</pages><issn>1024-2422</issn><eissn>1029-2446</eissn><abstract>Both enantiomers of the potential anti-anginal drug ranolazine have been synthesized from enantiopure (R)- and (S)-3-chloro-1-(2-methoxyphenoxy)propan-2-ol. These chiral building blocks were produced by kinetic resolution of the corresponding racemic butanoate by hydrolysis catalyzed by immobilized lipase from Rhizomucor miehei (Lipozym RM IM) or lipase B from Candida antarctica (Novozym 435). (R)-3-Chloro-1-(2-methoxyphenoxy)propan-2-ol was also made from the racemate in high yield and ee in a stereoinversion reaction.</abstract><cop>Abingdon</cop><pub>Informa UK Ltd</pub><doi>10.1080/10242420500067357</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1024-2422 |
| ispartof | Biocatalysis and biotransformation, 2005-01, Vol.23 (1), p.45-51 |
| issn | 1024-2422 1029-2446 |
| language | eng |
| recordid | cdi_pascalfrancis_primary_16697011 |
| source | Taylor & Francis |
| subjects | Angina Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Candida antarctica capillary electrophoresis chiral analysis Fundamental and applied biological sciences. Psychology highly sulfated cyklodextrins kinetic resolution Methods. Procedures. Technologies ranexa ranolazine Rhizomucor miehei stereoinversion |
| title | Chemo-enzymatic synthesis of both enantiomers of the anti-anginal drug ranolazine |
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