Effects of cell stress protectant glutathione on the whole-cell biotransformation of ethyl 2-chloro-acetoacetate with Saccharomyces cerevisiae
The whole-cell biotransformation of the β-keto ester ethyl 2-chloro-acetoacetate to ethyl (2R,3S)-2-chloro-3-hydroxybutyrate with Saccharomyces cerevisiae was investigated. Due to the xenobiotic stress exerted by the alkylating substrate, several competing reactions (up to 54%) were encountered at t...
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| Veröffentlicht in: | Biocatalysis and biotransformation 2005-01, Vol.23 (1), p.9-17 |
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| creator | Jörg, G. Hémery, T. Bertau, M. |
| description | The whole-cell biotransformation of the β-keto ester ethyl 2-chloro-acetoacetate to ethyl (2R,3S)-2-chloro-3-hydroxybutyrate with Saccharomyces cerevisiae was investigated. Due to the xenobiotic stress exerted by the alkylating substrate, several competing reactions (up to 54%) were encountered at the activated positions of the substrate molecule which are mediated by cytosolic glutathione (GSH): reductive dehalogenation, ester hydrolysis and cleavage of the C4-backbone (retro-Claisen condensation). The catalytic effect of a glutathione S-transferase accelerates these processes, but is not necessarily required for the reactions to occur. The ester hydrolysis product chloro-acetone and retro-Claisen product ethyl chloro-acetate significantly affect the stereoselectivity of the whole-cell reduction. However, for the dehalogenation product ethyl (S)-3-hydroxybutyrate no effects on the biotransformation were observed. |
| doi_str_mv | 10.1080/10242420500068231 |
| format | Article |
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Due to the xenobiotic stress exerted by the alkylating substrate, several competing reactions (up to 54%) were encountered at the activated positions of the substrate molecule which are mediated by cytosolic glutathione (GSH): reductive dehalogenation, ester hydrolysis and cleavage of the C4-backbone (retro-Claisen condensation). The catalytic effect of a glutathione S-transferase accelerates these processes, but is not necessarily required for the reactions to occur. The ester hydrolysis product chloro-acetone and retro-Claisen product ethyl chloro-acetate significantly affect the stereoselectivity of the whole-cell reduction. However, for the dehalogenation product ethyl (S)-3-hydroxybutyrate no effects on the biotransformation were observed.</description><identifier>ISSN: 1024-2422</identifier><identifier>EISSN: 1029-2446</identifier><identifier>DOI: 10.1080/10242420500068231</identifier><language>eng</language><publisher>Abingdon: Informa UK Ltd</publisher><subject>Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Biotransformation ; dehalogenation ; Fundamental and applied biological sciences. Psychology ; glutathione ; Methods. Procedures. 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Due to the xenobiotic stress exerted by the alkylating substrate, several competing reactions (up to 54%) were encountered at the activated positions of the substrate molecule which are mediated by cytosolic glutathione (GSH): reductive dehalogenation, ester hydrolysis and cleavage of the C4-backbone (retro-Claisen condensation). The catalytic effect of a glutathione S-transferase accelerates these processes, but is not necessarily required for the reactions to occur. The ester hydrolysis product chloro-acetone and retro-Claisen product ethyl chloro-acetate significantly affect the stereoselectivity of the whole-cell reduction. However, for the dehalogenation product ethyl (S)-3-hydroxybutyrate no effects on the biotransformation were observed.</description><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Biotransformation</subject><subject>dehalogenation</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>glutathione</subject><subject>Methods. Procedures. 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Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Biotransformation</topic><topic>dehalogenation</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>glutathione</topic><topic>Methods. Procedures. Technologies</topic><topic>Saccharomyces cerevisiae</topic><topic>stereoselective reduction</topic><topic>xenobiotic stress</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jörg, G.</creatorcontrib><creatorcontrib>Hémery, T.</creatorcontrib><creatorcontrib>Bertau, M.</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>Jörg, G.</au><au>Hémery, T.</au><au>Bertau, M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effects of cell stress protectant glutathione on the whole-cell biotransformation of ethyl 2-chloro-acetoacetate with Saccharomyces cerevisiae</atitle><jtitle>Biocatalysis and biotransformation</jtitle><date>2005-01-01</date><risdate>2005</risdate><volume>23</volume><issue>1</issue><spage>9</spage><epage>17</epage><pages>9-17</pages><issn>1024-2422</issn><eissn>1029-2446</eissn><abstract>The whole-cell biotransformation of the β-keto ester ethyl 2-chloro-acetoacetate to ethyl (2R,3S)-2-chloro-3-hydroxybutyrate with Saccharomyces cerevisiae was investigated. Due to the xenobiotic stress exerted by the alkylating substrate, several competing reactions (up to 54%) were encountered at the activated positions of the substrate molecule which are mediated by cytosolic glutathione (GSH): reductive dehalogenation, ester hydrolysis and cleavage of the C4-backbone (retro-Claisen condensation). The catalytic effect of a glutathione S-transferase accelerates these processes, but is not necessarily required for the reactions to occur. The ester hydrolysis product chloro-acetone and retro-Claisen product ethyl chloro-acetate significantly affect the stereoselectivity of the whole-cell reduction. However, for the dehalogenation product ethyl (S)-3-hydroxybutyrate no effects on the biotransformation were observed.</abstract><cop>Abingdon</cop><pub>Informa UK Ltd</pub><doi>10.1080/10242420500068231</doi><tpages>9</tpages></addata></record> |
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| subjects | Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Biotransformation dehalogenation Fundamental and applied biological sciences. Psychology glutathione Methods. Procedures. Technologies Saccharomyces cerevisiae stereoselective reduction xenobiotic stress |
| title | Effects of cell stress protectant glutathione on the whole-cell biotransformation of ethyl 2-chloro-acetoacetate with Saccharomyces cerevisiae |
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