Resolution of Mandelic Acids by Lipase-Catalyzed Transesterifications in Organic Media
The resolution of mandelic acids was achieved via two types of lipase-catalyzed transesterifications in organic media, i.e., deacylation (alcoholysis) of O-acylated mandelates and acylation (transesterification) of mandelates. Through deacylation with butanol of methyl O-butyryl-(RS)-mandelates with...
Gespeichert in:
| Veröffentlicht in: | Biocatalysis and biotransformation 2000, Vol.17 (6), p.459-473 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 473 |
|---|---|
| container_issue | 6 |
| container_start_page | 459 |
| container_title | Biocatalysis and biotransformation |
| container_volume | 17 |
| creator | Miyazawa, Toshifumi Kurita, Sota Ueji, Shinichi Yamada, Takashi |
| description | The resolution of mandelic acids was achieved via two types of lipase-catalyzed transesterifications in organic media, i.e., deacylation (alcoholysis) of O-acylated mandelates and acylation (transesterification) of mandelates. Through deacylation with butanol of methyl O-butyryl-(RS)-mandelates with or without a p-substituent, (S)-mandelates with 97% ee were produced at ca. 40% conversion (E 100) using Penicillium roqueforti lipase in isopropyl ether. Through acylation with vinyl acetate of methyl (RS)-mandelates, the free (R)-mandelates with 98% ee were obtained as recovered substrates at ca. 60% conversion (E 15) using Pseudomonas sp. lipase in the same solvent. According to the latter strategy, optically pure (> 99% ee) methyl (R)-mandelates were prepared on a gram scale. In the acylation reactions, vinyl esters carrying a shorter alkyl chain served as better acyl donors in terms of the conversion rate, while the enantioselectivity was the highest with vinyl butyrate. Additionally the stereochemical preference of the enzyme was inverted from S to R by using vinyl chloroacetate as the acyl donor. |
| doi_str_mv | 10.3109/10242420009003636 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_17503669</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>458828</sourcerecordid><originalsourceid>FETCH-LOGICAL-c439t-cdd7ee269816303f65a5ce1c69c5c22e7266664039b69cb4a80c05e230f5cf873</originalsourceid><addsrcrecordid>eNqFkE1LAzEQhhdRsFZ_gLc9iLfVfOxmG_QixS9oKUj1ukyzE5uSbmqyReqvN7UVEaFmDhnC-0yGJ0lOKbnglMhLSlgeixAiCeGCi72kE99kxvJc7H_1eewZO0yOQpgRQjmTZSd5ecLg7LI1rkmdTofQ1GiNSm-UqUM6WaUDs4CAWR9asKsPrNOxhyZgaNEbbRSsyZCaJh35V2giOcTawHFyoMEGPNne3eT57nbcf8gGo_vH_s0gUzmXbabqukRkQvao4IRrUUChkCohVaEYw5KJeHLC5SQ-TXLoEUUKZJzoQuleybvJ-Wbuwru3Zdyqmpug0Fpo0C1DxSjvFVHHv0FaFlGbkDFIN0HlXQgedbXwZg5-VVFSrVVXf1RH5mw7HIICq6MhZcIPyIpYeYxdb2Km0c7P4d15W1ctrKzz3wzf9cvVL3yKYNupAo_VzC19Ez3v2PETZVmiEw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>17503669</pqid></control><display><type>article</type><title>Resolution of Mandelic Acids by Lipase-Catalyzed Transesterifications in Organic Media</title><source>Taylor & Francis:Master (3349 titles)</source><creator>Miyazawa, Toshifumi ; Kurita, Sota ; Ueji, Shinichi ; Yamada, Takashi</creator><creatorcontrib>Miyazawa, Toshifumi ; Kurita, Sota ; Ueji, Shinichi ; Yamada, Takashi</creatorcontrib><description>The resolution of mandelic acids was achieved via two types of lipase-catalyzed transesterifications in organic media, i.e., deacylation (alcoholysis) of O-acylated mandelates and acylation (transesterification) of mandelates. Through deacylation with butanol of methyl O-butyryl-(RS)-mandelates with or without a p-substituent, (S)-mandelates with 97% ee were produced at ca. 40% conversion (E 100) using Penicillium roqueforti lipase in isopropyl ether. Through acylation with vinyl acetate of methyl (RS)-mandelates, the free (R)-mandelates with 98% ee were obtained as recovered substrates at ca. 60% conversion (E 15) using Pseudomonas sp. lipase in the same solvent. According to the latter strategy, optically pure (> 99% ee) methyl (R)-mandelates were prepared on a gram scale. In the acylation reactions, vinyl esters carrying a shorter alkyl chain served as better acyl donors in terms of the conversion rate, while the enantioselectivity was the highest with vinyl butyrate. Additionally the stereochemical preference of the enzyme was inverted from S to R by using vinyl chloroacetate as the acyl donor.</description><identifier>ISSN: 1024-2422</identifier><identifier>EISSN: 1029-2446</identifier><identifier>DOI: 10.3109/10242420009003636</identifier><language>eng</language><publisher>Abingdon: Informa UK Ltd</publisher><subject>Acylation ; Alcohols ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Catalysis ; Enantioselectivity ; Enzymes ; Esterification ; Esters ; Fundamental and applied biological sciences. Psychology ; Lipases ; mandelic acid ; Mandelic acids ; Methods. Procedures. Technologies ; Optical resolution ; Organic compounds ; Penicillium roqueforti ; Pseudomonas ; Transesterifications ; Vinyl esters</subject><ispartof>Biocatalysis and biotransformation, 2000, Vol.17 (6), p.459-473</ispartof><rights>2000 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 2000</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c439t-cdd7ee269816303f65a5ce1c69c5c22e7266664039b69cb4a80c05e230f5cf873</citedby><cites>FETCH-LOGICAL-c439t-cdd7ee269816303f65a5ce1c69c5c22e7266664039b69cb4a80c05e230f5cf873</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.3109/10242420009003636$$EPDF$$P50$$Ginformahealthcare$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.3109/10242420009003636$$EHTML$$P50$$Ginformahealthcare$$H</linktohtml><link.rule.ids>314,776,780,4010,27900,27901,27902,59620,60409,61194,61375</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1252524$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Miyazawa, Toshifumi</creatorcontrib><creatorcontrib>Kurita, Sota</creatorcontrib><creatorcontrib>Ueji, Shinichi</creatorcontrib><creatorcontrib>Yamada, Takashi</creatorcontrib><title>Resolution of Mandelic Acids by Lipase-Catalyzed Transesterifications in Organic Media</title><title>Biocatalysis and biotransformation</title><description>The resolution of mandelic acids was achieved via two types of lipase-catalyzed transesterifications in organic media, i.e., deacylation (alcoholysis) of O-acylated mandelates and acylation (transesterification) of mandelates. Through deacylation with butanol of methyl O-butyryl-(RS)-mandelates with or without a p-substituent, (S)-mandelates with 97% ee were produced at ca. 40% conversion (E 100) using Penicillium roqueforti lipase in isopropyl ether. Through acylation with vinyl acetate of methyl (RS)-mandelates, the free (R)-mandelates with 98% ee were obtained as recovered substrates at ca. 60% conversion (E 15) using Pseudomonas sp. lipase in the same solvent. According to the latter strategy, optically pure (> 99% ee) methyl (R)-mandelates were prepared on a gram scale. In the acylation reactions, vinyl esters carrying a shorter alkyl chain served as better acyl donors in terms of the conversion rate, while the enantioselectivity was the highest with vinyl butyrate. Additionally the stereochemical preference of the enzyme was inverted from S to R by using vinyl chloroacetate as the acyl donor.</description><subject>Acylation</subject><subject>Alcohols</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Catalysis</subject><subject>Enantioselectivity</subject><subject>Enzymes</subject><subject>Esterification</subject><subject>Esters</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Lipases</subject><subject>mandelic acid</subject><subject>Mandelic acids</subject><subject>Methods. Procedures. Technologies</subject><subject>Optical resolution</subject><subject>Organic compounds</subject><subject>Penicillium roqueforti</subject><subject>Pseudomonas</subject><subject>Transesterifications</subject><subject>Vinyl esters</subject><issn>1024-2422</issn><issn>1029-2446</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LAzEQhhdRsFZ_gLc9iLfVfOxmG_QixS9oKUj1ukyzE5uSbmqyReqvN7UVEaFmDhnC-0yGJ0lOKbnglMhLSlgeixAiCeGCi72kE99kxvJc7H_1eewZO0yOQpgRQjmTZSd5ecLg7LI1rkmdTofQ1GiNSm-UqUM6WaUDs4CAWR9asKsPrNOxhyZgaNEbbRSsyZCaJh35V2giOcTawHFyoMEGPNne3eT57nbcf8gGo_vH_s0gUzmXbabqukRkQvao4IRrUUChkCohVaEYw5KJeHLC5SQ-TXLoEUUKZJzoQuleybvJ-Wbuwru3Zdyqmpug0Fpo0C1DxSjvFVHHv0FaFlGbkDFIN0HlXQgedbXwZg5-VVFSrVVXf1RH5mw7HIICq6MhZcIPyIpYeYxdb2Km0c7P4d15W1ctrKzz3wzf9cvVL3yKYNupAo_VzC19Ez3v2PETZVmiEw</recordid><startdate>2000</startdate><enddate>2000</enddate><creator>Miyazawa, Toshifumi</creator><creator>Kurita, Sota</creator><creator>Ueji, Shinichi</creator><creator>Yamada, Takashi</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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>2000</creationdate><title>Resolution of Mandelic Acids by Lipase-Catalyzed Transesterifications in Organic Media</title><author>Miyazawa, Toshifumi ; Kurita, Sota ; Ueji, Shinichi ; Yamada, Takashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c439t-cdd7ee269816303f65a5ce1c69c5c22e7266664039b69cb4a80c05e230f5cf873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Acylation</topic><topic>Alcohols</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Catalysis</topic><topic>Enantioselectivity</topic><topic>Enzymes</topic><topic>Esterification</topic><topic>Esters</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Lipases</topic><topic>mandelic acid</topic><topic>Mandelic acids</topic><topic>Methods. Procedures. Technologies</topic><topic>Optical resolution</topic><topic>Organic compounds</topic><topic>Penicillium roqueforti</topic><topic>Pseudomonas</topic><topic>Transesterifications</topic><topic>Vinyl esters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miyazawa, Toshifumi</creatorcontrib><creatorcontrib>Kurita, Sota</creatorcontrib><creatorcontrib>Ueji, Shinichi</creatorcontrib><creatorcontrib>Yamada, Takashi</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</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>Miyazawa, Toshifumi</au><au>Kurita, Sota</au><au>Ueji, Shinichi</au><au>Yamada, Takashi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Resolution of Mandelic Acids by Lipase-Catalyzed Transesterifications in Organic Media</atitle><jtitle>Biocatalysis and biotransformation</jtitle><date>2000</date><risdate>2000</risdate><volume>17</volume><issue>6</issue><spage>459</spage><epage>473</epage><pages>459-473</pages><issn>1024-2422</issn><eissn>1029-2446</eissn><abstract>The resolution of mandelic acids was achieved via two types of lipase-catalyzed transesterifications in organic media, i.e., deacylation (alcoholysis) of O-acylated mandelates and acylation (transesterification) of mandelates. Through deacylation with butanol of methyl O-butyryl-(RS)-mandelates with or without a p-substituent, (S)-mandelates with 97% ee were produced at ca. 40% conversion (E 100) using Penicillium roqueforti lipase in isopropyl ether. Through acylation with vinyl acetate of methyl (RS)-mandelates, the free (R)-mandelates with 98% ee were obtained as recovered substrates at ca. 60% conversion (E 15) using Pseudomonas sp. lipase in the same solvent. According to the latter strategy, optically pure (> 99% ee) methyl (R)-mandelates were prepared on a gram scale. In the acylation reactions, vinyl esters carrying a shorter alkyl chain served as better acyl donors in terms of the conversion rate, while the enantioselectivity was the highest with vinyl butyrate. Additionally the stereochemical preference of the enzyme was inverted from S to R by using vinyl chloroacetate as the acyl donor.</abstract><cop>Abingdon</cop><pub>Informa UK Ltd</pub><doi>10.3109/10242420009003636</doi><tpages>15</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1024-2422 |
| ispartof | Biocatalysis and biotransformation, 2000, Vol.17 (6), p.459-473 |
| issn | 1024-2422 1029-2446 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_17503669 |
| source | Taylor & Francis:Master (3349 titles) |
| subjects | Acylation Alcohols Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Catalysis Enantioselectivity Enzymes Esterification Esters Fundamental and applied biological sciences. Psychology Lipases mandelic acid Mandelic acids Methods. Procedures. Technologies Optical resolution Organic compounds Penicillium roqueforti Pseudomonas Transesterifications Vinyl esters |
| title | Resolution of Mandelic Acids by Lipase-Catalyzed Transesterifications in Organic Media |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T12%3A24%3A20IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Resolution%20of%20Mandelic%20Acids%20by%20Lipase-Catalyzed%20Transesterifications%20in%20Organic%20Media&rft.jtitle=Biocatalysis%20and%20biotransformation&rft.au=Miyazawa,%20Toshifumi&rft.date=2000&rft.volume=17&rft.issue=6&rft.spage=459&rft.epage=473&rft.pages=459-473&rft.issn=1024-2422&rft.eissn=1029-2446&rft_id=info:doi/10.3109/10242420009003636&rft_dat=%3Cproquest_cross%3E458828%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=17503669&rft_id=info:pmid/&rfr_iscdi=true |