Enzymatic Preparation of Optically Active Carboxylic Acids and Their Applications
The application of enzymes or microorganisms to an organic synthesis is one of the most useful and practical methods for the preparation of optically active compounds. We have developed a novel process for enzymatic preparation of D- (-) -β-acetylthioisobutyric acid. A newly isolated strain, Pseudom...
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Veröffentlicht in: | Journal of Synthetic Organic Chemistry, Japan Japan, 1997/07/01, Vol.55(7), pp.642-650 |
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container_title | Journal of Synthetic Organic Chemistry, Japan |
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creator | OZAKI, Eiji URAGAKI, Toshitaka SAKASHITA, Keiichi SAKIMAE, Akihiro |
description | The application of enzymes or microorganisms to an organic synthesis is one of the most useful and practical methods for the preparation of optically active compounds. We have developed a novel process for enzymatic preparation of D- (-) -β-acetylthioisobutyric acid. A newly isolated strain, Pseudomonas putida MR-2068, produced an attractive esterase. A gene for the esterase was cloned and expressed in the Escherichia coli cells. The result of a sequence analysis and some characteristics of the purified enzyme are described. This esterase also catalyzed regio- and enantioselective hydrolysis of α-substituted carboxylic acid esters. Considering the results of enzymatic reactions, the active site model of enzyme is tentatively proposed. |
doi_str_mv | 10.5059/yukigoseikyokaishi.55.642 |
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We have developed a novel process for enzymatic preparation of D- (-) -β-acetylthioisobutyric acid. A newly isolated strain, Pseudomonas putida MR-2068, produced an attractive esterase. A gene for the esterase was cloned and expressed in the Escherichia coli cells. The result of a sequence analysis and some characteristics of the purified enzyme are described. This esterase also catalyzed regio- and enantioselective hydrolysis of α-substituted carboxylic acid esters. 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Synth. Org. Chem. Jpn.</addtitle><description>The application of enzymes or microorganisms to an organic synthesis is one of the most useful and practical methods for the preparation of optically active compounds. We have developed a novel process for enzymatic preparation of D- (-) -β-acetylthioisobutyric acid. A newly isolated strain, Pseudomonas putida MR-2068, produced an attractive esterase. A gene for the esterase was cloned and expressed in the Escherichia coli cells. The result of a sequence analysis and some characteristics of the purified enzyme are described. This esterase also catalyzed regio- and enantioselective hydrolysis of α-substituted carboxylic acid esters. Considering the results of enzymatic reactions, the active site model of enzyme is tentatively proposed.</description><subject>ACE inhibitor</subject><subject>Active site model</subject><subject>Esterase</subject><subject>Genetic engineering</subject><subject>Microorganisms</subject><subject>Optical resolution</subject><subject>Pseudomonas putida</subject><subject>α-Methyl carboxylic acid</subject><issn>0037-9980</issn><issn>1883-6526</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><recordid>eNptkNtOwzAMhiMEEtPYO4QH6MihbpvLahoHadIAjesoTdItW9dWyUCUpydjaDfgC9uy_P2yf4RuKZkCAXE3vO_cugvW7YZup1zYuCnANEvZBRrRouBJBiy7RCNCeJ4IUZBrNAlhS2LwQlAuRuhl3n4Ne3VwGj972ysf267FXY2XfRyqphlwqQ_uw-KZ8lX3OTRxtdTOBKxag1cb6zwu-z6Of9Bwg65q1QQ7-a1j9HY_X80ek8Xy4WlWLhLNOGOJIpBDlWrDNEtNxQTQVFFDc2rztM4KnoOmholcGGOtAVIoHi-2hoCugVZ8jMRJV_suBG9r2Xu3V36QlMijPfKvPRJARnsi-3pit-Gg1vZMKh9_buw_JBUpP9L5KUWR87LeKC9ty78BMK5-ug</recordid><startdate>19970701</startdate><enddate>19970701</enddate><creator>OZAKI, Eiji</creator><creator>URAGAKI, Toshitaka</creator><creator>SAKASHITA, Keiichi</creator><creator>SAKIMAE, Akihiro</creator><general>The Society of Synthetic Organic Chemistry, Japan</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19970701</creationdate><title>Enzymatic Preparation of Optically Active Carboxylic Acids and Their Applications</title><author>OZAKI, Eiji ; URAGAKI, Toshitaka ; SAKASHITA, Keiichi ; SAKIMAE, Akihiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2322-a0575b4cd2c24db29514a1d171e74f68375c1d2979ddeed508a3139ed05cf51b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>ACE inhibitor</topic><topic>Active site model</topic><topic>Esterase</topic><topic>Genetic engineering</topic><topic>Microorganisms</topic><topic>Optical resolution</topic><topic>Pseudomonas putida</topic><topic>α-Methyl carboxylic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>OZAKI, Eiji</creatorcontrib><creatorcontrib>URAGAKI, Toshitaka</creatorcontrib><creatorcontrib>SAKASHITA, Keiichi</creatorcontrib><creatorcontrib>SAKIMAE, Akihiro</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of Synthetic Organic Chemistry, Japan</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>OZAKI, Eiji</au><au>URAGAKI, Toshitaka</au><au>SAKASHITA, Keiichi</au><au>SAKIMAE, Akihiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enzymatic Preparation of Optically Active Carboxylic Acids and Their Applications</atitle><jtitle>Journal of Synthetic Organic Chemistry, Japan</jtitle><addtitle>J. Synth. Org. Chem. Jpn.</addtitle><date>1997-07-01</date><risdate>1997</risdate><volume>55</volume><issue>7</issue><spage>642</spage><epage>650</epage><pages>642-650</pages><issn>0037-9980</issn><eissn>1883-6526</eissn><abstract>The application of enzymes or microorganisms to an organic synthesis is one of the most useful and practical methods for the preparation of optically active compounds. We have developed a novel process for enzymatic preparation of D- (-) -β-acetylthioisobutyric acid. A newly isolated strain, Pseudomonas putida MR-2068, produced an attractive esterase. A gene for the esterase was cloned and expressed in the Escherichia coli cells. The result of a sequence analysis and some characteristics of the purified enzyme are described. This esterase also catalyzed regio- and enantioselective hydrolysis of α-substituted carboxylic acid esters. 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subjects | ACE inhibitor Active site model Esterase Genetic engineering Microorganisms Optical resolution Pseudomonas putida α-Methyl carboxylic acid |
title | Enzymatic Preparation of Optically Active Carboxylic Acids and Their Applications |
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