Microbial Asymmetric Reduction. Preparation of Optically Active Methyl trans-3-(4-Methoxyphenyl)Glycidates

Microbial Asymmetric Reduction. Preparation of Optically Active Methyl trans-3-(4-Methoxyphenyl)Glycidates

As a result of screening of microorganisms, Mucor ambiguus IFO 6742 was found to reduce methyl 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate (2) to give methyl (2S,3R)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate [(2S,3R)-3] in good yield with high enantioselectivity. The resulting (2S, 3R)-3 was...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Biocatalysis and biotransformation 1995, Vol.12 (3), p.205-214
Hauptverfasser: Nishida, Takuo, Matsumae, Hiroaki, Machida, Ikuko, Shibatani, Takeji
Format: Artikel
Sprache:eng
Schlagworte:
diltiazem hydrochloride
methy 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate
Microbial asymmetric reduction
optically active methyl 2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate
optically active methyl trants-3-(4-methoxyphenyl)glycidate
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 214
container_issue 3
container_start_page 205
container_title Biocatalysis and biotransformation
container_volume 12
creator Nishida, Takuo
Matsumae, Hiroaki
Machida, Ikuko
Shibatani, Takeji
description As a result of screening of microorganisms, Mucor ambiguus IFO 6742 was found to reduce methyl 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate (2) to give methyl (2S,3R)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate [(2S,3R)-3] in good yield with high enantioselectivity. The resulting (2S, 3R)-3 was converted into methyl (2S,3R)-3-(4-methoxyphenyl)glycidate [(2S,3R)-4] by treatment with sodium methoxide. On the other hand, its enantiomer, (2R,3S)-4 was obtained by the Mitsunobu esterification of (2S,3R)-3 and subsequent treatment with sodium methoxide. Also (2R,3S)-4 was obtained by the treatment of (2RS,3S)-3, which was obtained from 2 by Trichoderma viride OUT 4642, with sodium methoxide.
doi_str_mv 10.3109/10242429508998163
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_3109_10242429508998163</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>17047231</sourcerecordid><originalsourceid>FETCH-LOGICAL-c481t-a6c72272414e2aa9ecffa9e11609f906f27ca579b3b20979ef0f0cac8d9f9eed3</originalsourceid><addsrcrecordid>eNp9kE1LxDAQhosoqKs_wFtPoodqksZ2g16WxS9wWRE9l9l0wmZJm5qkav-9WdeLiBJIJpP3mcCTJEeUnOWUiHNKGI9LXJCxEGNa5FvJXuyJjHFebH_VPNaM7Sb73q8IoTkT5V6ymmnp7EKDSSd-aBoMTsv0CeteBm3bs_TRYQcO1pfUqnTeBS3BmCGdxMAbpjMMy8GkwUHrszw74dm6Yz-GbontYE5vzSB1DQH9QbKjwHg8_D5HycvN9fP0LnuY395PJw-Z5GMaMihkyVjJOOXIAARKpeJOaUGEEqRQrJRwUYpFvmBElAIVUUSCHNfxGbHOR8nxZm7n7GuPPlSN9hKNgRZt7ytaEl6ynMYg3QSjAe8dqqpzugE3VJRUa6vVL6uRudowulXWNfBunamrAIOxTkUHUvs1-jd--QNfIpiwlOCwWtnetdHLP59_AsyqkUQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>17047231</pqid></control><display><type>article</type><title>Microbial Asymmetric Reduction. Preparation of Optically Active Methyl trans-3-(4-Methoxyphenyl)Glycidates</title><source>Taylor &amp; Francis Journals Complete</source><creator>Nishida, Takuo ; Matsumae, Hiroaki ; Machida, Ikuko ; Shibatani, Takeji</creator><creatorcontrib>Nishida, Takuo ; Matsumae, Hiroaki ; Machida, Ikuko ; Shibatani, Takeji</creatorcontrib><description>As a result of screening of microorganisms, Mucor ambiguus IFO 6742 was found to reduce methyl 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate (2) to give methyl (2S,3R)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate [(2S,3R)-3] in good yield with high enantioselectivity. The resulting (2S, 3R)-3 was converted into methyl (2S,3R)-3-(4-methoxyphenyl)glycidate [(2S,3R)-4] by treatment with sodium methoxide. On the other hand, its enantiomer, (2R,3S)-4 was obtained by the Mitsunobu esterification of (2S,3R)-3 and subsequent treatment with sodium methoxide. Also (2R,3S)-4 was obtained by the treatment of (2RS,3S)-3, which was obtained from 2 by Trichoderma viride OUT 4642, with sodium methoxide.</description><identifier>ISSN: 1024-2422</identifier><identifier>EISSN: 1029-2446</identifier><identifier>DOI: 10.3109/10242429508998163</identifier><language>eng</language><publisher>Informa UK Ltd</publisher><subject>diltiazem hydrochloride ; methy 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate ; Microbial asymmetric reduction ; optically active methyl 2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate ; optically active methyl trants-3-(4-methoxyphenyl)glycidate</subject><ispartof>Biocatalysis and biotransformation, 1995, Vol.12 (3), p.205-214</ispartof><rights>1995 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 1995</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c481t-a6c72272414e2aa9ecffa9e11609f906f27ca579b3b20979ef0f0cac8d9f9eed3</citedby><cites>FETCH-LOGICAL-c481t-a6c72272414e2aa9ecffa9e11609f906f27ca579b3b20979ef0f0cac8d9f9eed3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.3109/10242429508998163$$EPDF$$P50$$Ginformahealthcare$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.3109/10242429508998163$$EHTML$$P50$$Ginformahealthcare$$H</linktohtml><link.rule.ids>314,780,784,4022,27922,27923,27924,59646,60435,61220,61401</link.rule.ids></links><search><creatorcontrib>Nishida, Takuo</creatorcontrib><creatorcontrib>Matsumae, Hiroaki</creatorcontrib><creatorcontrib>Machida, Ikuko</creatorcontrib><creatorcontrib>Shibatani, Takeji</creatorcontrib><title>Microbial Asymmetric Reduction. Preparation of Optically Active Methyl trans-3-(4-Methoxyphenyl)Glycidates</title><title>Biocatalysis and biotransformation</title><description>As a result of screening of microorganisms, Mucor ambiguus IFO 6742 was found to reduce methyl 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate (2) to give methyl (2S,3R)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate [(2S,3R)-3] in good yield with high enantioselectivity. The resulting (2S, 3R)-3 was converted into methyl (2S,3R)-3-(4-methoxyphenyl)glycidate [(2S,3R)-4] by treatment with sodium methoxide. On the other hand, its enantiomer, (2R,3S)-4 was obtained by the Mitsunobu esterification of (2S,3R)-3 and subsequent treatment with sodium methoxide. Also (2R,3S)-4 was obtained by the treatment of (2RS,3S)-3, which was obtained from 2 by Trichoderma viride OUT 4642, with sodium methoxide.</description><subject>diltiazem hydrochloride</subject><subject>methy 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate</subject><subject>Microbial asymmetric reduction</subject><subject>optically active methyl 2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate</subject><subject>optically active methyl trants-3-(4-methoxyphenyl)glycidate</subject><issn>1024-2422</issn><issn>1029-2446</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LxDAQhosoqKs_wFtPoodqksZ2g16WxS9wWRE9l9l0wmZJm5qkav-9WdeLiBJIJpP3mcCTJEeUnOWUiHNKGI9LXJCxEGNa5FvJXuyJjHFebH_VPNaM7Sb73q8IoTkT5V6ymmnp7EKDSSd-aBoMTsv0CeteBm3bs_TRYQcO1pfUqnTeBS3BmCGdxMAbpjMMy8GkwUHrszw74dm6Yz-GbontYE5vzSB1DQH9QbKjwHg8_D5HycvN9fP0LnuY395PJw-Z5GMaMihkyVjJOOXIAARKpeJOaUGEEqRQrJRwUYpFvmBElAIVUUSCHNfxGbHOR8nxZm7n7GuPPlSN9hKNgRZt7ytaEl6ynMYg3QSjAe8dqqpzugE3VJRUa6vVL6uRudowulXWNfBunamrAIOxTkUHUvs1-jd--QNfIpiwlOCwWtnetdHLP59_AsyqkUQ</recordid><startdate>1995</startdate><enddate>1995</enddate><creator>Nishida, Takuo</creator><creator>Matsumae, Hiroaki</creator><creator>Machida, Ikuko</creator><creator>Shibatani, Takeji</creator><general>Informa UK Ltd</general><general>Taylor &amp; Francis</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>1995</creationdate><title>Microbial Asymmetric Reduction. Preparation of Optically Active Methyl trans-3-(4-Methoxyphenyl)Glycidates</title><author>Nishida, Takuo ; Matsumae, Hiroaki ; Machida, Ikuko ; Shibatani, Takeji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c481t-a6c72272414e2aa9ecffa9e11609f906f27ca579b3b20979ef0f0cac8d9f9eed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>diltiazem hydrochloride</topic><topic>methy 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate</topic><topic>Microbial asymmetric reduction</topic><topic>optically active methyl 2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate</topic><topic>optically active methyl trants-3-(4-methoxyphenyl)glycidate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nishida, Takuo</creatorcontrib><creatorcontrib>Matsumae, Hiroaki</creatorcontrib><creatorcontrib>Machida, Ikuko</creatorcontrib><creatorcontrib>Shibatani, Takeji</creatorcontrib><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>Nishida, Takuo</au><au>Matsumae, Hiroaki</au><au>Machida, Ikuko</au><au>Shibatani, Takeji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microbial Asymmetric Reduction. Preparation of Optically Active Methyl trans-3-(4-Methoxyphenyl)Glycidates</atitle><jtitle>Biocatalysis and biotransformation</jtitle><date>1995</date><risdate>1995</risdate><volume>12</volume><issue>3</issue><spage>205</spage><epage>214</epage><pages>205-214</pages><issn>1024-2422</issn><eissn>1029-2446</eissn><abstract>As a result of screening of microorganisms, Mucor ambiguus IFO 6742 was found to reduce methyl 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate (2) to give methyl (2S,3R)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate [(2S,3R)-3] in good yield with high enantioselectivity. The resulting (2S, 3R)-3 was converted into methyl (2S,3R)-3-(4-methoxyphenyl)glycidate [(2S,3R)-4] by treatment with sodium methoxide. On the other hand, its enantiomer, (2R,3S)-4 was obtained by the Mitsunobu esterification of (2S,3R)-3 and subsequent treatment with sodium methoxide. Also (2R,3S)-4 was obtained by the treatment of (2RS,3S)-3, which was obtained from 2 by Trichoderma viride OUT 4642, with sodium methoxide.</abstract><pub>Informa UK Ltd</pub><doi>10.3109/10242429508998163</doi><tpages>10</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1024-2422
ispartof Biocatalysis and biotransformation, 1995, Vol.12 (3), p.205-214
issn 1024-2422
1029-2446
language eng
recordid cdi_crossref_primary_10_3109_10242429508998163
source Taylor & Francis Journals Complete
subjects diltiazem hydrochloride
methy 2-chloro-3-(4-methoxyphenyl)-3-oxopropionate
Microbial asymmetric reduction
optically active methyl 2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate
optically active methyl trants-3-(4-methoxyphenyl)glycidate
title Microbial Asymmetric Reduction. Preparation of Optically Active Methyl trans-3-(4-Methoxyphenyl)Glycidates
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T16%3A57%3A18IST&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=Microbial%20Asymmetric%20Reduction.%20Preparation%20of%20Optically%20Active%20Methyl%20trans-3-(4-Methoxyphenyl)Glycidates&rft.jtitle=Biocatalysis%20and%20biotransformation&rft.au=Nishida,%20Takuo&rft.date=1995&rft.volume=12&rft.issue=3&rft.spage=205&rft.epage=214&rft.pages=205-214&rft.issn=1024-2422&rft.eissn=1029-2446&rft_id=info:doi/10.3109/10242429508998163&rft_dat=%3Cproquest_cross%3E17047231%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=17047231&rft_id=info:pmid/&rfr_iscdi=true