Resolution of racemic sulfoxides with high productivity and enantioselectivity by a Rhodococcus sp. strain as an alternative to biooxidation of prochiral sulfides for efficient production of enantiopure sulfoxides
Whole cells of Rhodococcus sp. ECU0066 were used a catalyst for resolution of racemic sulfoxides, as an alternative to asymmetric oxidation of sulfides for efficient production of enantiopure sulfoxides. Racemic sulfoxides were excellent substrates for biotransformation because of their lower biotox...
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| Veröffentlicht in: | Bioresource technology 2011, Vol.102 (2), p.1537-1542 |
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| creator | Li, Ai-Tao Yu, Hui-Lei Pan, Jiang Zhang, Jian-Dong Xu, Jian-He Lin, Guo-Qiang |
| description | Whole cells of
Rhodococcus sp. ECU0066 were used a catalyst for resolution of racemic sulfoxides, as an alternative to asymmetric oxidation of sulfides for efficient production of enantiopure sulfoxides. Racemic sulfoxides were excellent substrates for biotransformation because of their lower biotoxicity compared to sulfides. Determination of apparent kinetic parameters indicated that phenyl methyl sulfide (PMS), but not racemic phenyl methyl sulfoxide (
rac-PMSO) caused substrate inhibition. (
S)-PMSO was formed at a higher concentration and good enantiomeric excess (37.8
mM and 93.7%
ee(
S)) in a fed-batch reaction, than by an asymmetric oxidation of PMS (10
mM and 80%
ee
P (
S)). The bacterium also displayed fairly good activity (yields, 22.7–43.2%; within 1–8
h) and enantioselectivity (
ee(
S)
>
99.0%) towards
para-substituted (methyl and chloro) phenyl methyl sulfoxides and ethyl phenyl sulfoxide, indicating it could be a promising agent for synthetic applications. |
| doi_str_mv | 10.1016/j.biortech.2010.08.025 |
| format | Article |
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Rhodococcus sp. ECU0066 were used a catalyst for resolution of racemic sulfoxides, as an alternative to asymmetric oxidation of sulfides for efficient production of enantiopure sulfoxides. Racemic sulfoxides were excellent substrates for biotransformation because of their lower biotoxicity compared to sulfides. Determination of apparent kinetic parameters indicated that phenyl methyl sulfide (PMS), but not racemic phenyl methyl sulfoxide (
rac-PMSO) caused substrate inhibition. (
S)-PMSO was formed at a higher concentration and good enantiomeric excess (37.8
mM and 93.7%
ee(
S)) in a fed-batch reaction, than by an asymmetric oxidation of PMS (10
mM and 80%
ee
P (
S)). The bacterium also displayed fairly good activity (yields, 22.7–43.2%; within 1–8
h) and enantioselectivity (
ee(
S)
>
99.0%) towards
para-substituted (methyl and chloro) phenyl methyl sulfoxides and ethyl phenyl sulfoxide, indicating it could be a promising agent for synthetic applications.</description><identifier>ISSN: 0960-8524</identifier><identifier>EISSN: 1873-2976</identifier><identifier>DOI: 10.1016/j.biortech.2010.08.025</identifier><identifier>PMID: 20810278</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>( S)-sulfoxides ; Asymmetry ; Biological and medical sciences ; Bioresolution ; Biotransformation ; Catalysis ; Fundamental and applied biological sciences. Psychology ; Hydrogen-Ion Concentration ; Kinetics ; Microbial Viability ; Oxidation ; Oxidation-Reduction ; Phenyl methyl sulfide ; Phenyls ; Productivity ; Racemic phenyl methyl sulfoxide ; Rhodococcus ; Rhodococcus - cytology ; Rhodococcus - metabolism ; Rhodococcus sp ; Stereoisomerism ; Strain ; Substrate inhibition ; Substrate Specificity ; Sulfides ; Sulfides - chemistry ; Sulfides - metabolism ; Sulfoxides - chemical synthesis ; Sulfoxides - chemistry ; Sulfoxides - metabolism ; Temperature ; Time Factors</subject><ispartof>Bioresource technology, 2011, Vol.102 (2), p.1537-1542</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c486t-2f0ff6d4e6836ec2eb50d0a0bb26ccab88dcbac900d4eba58bb8915ee00465963</citedby><cites>FETCH-LOGICAL-c486t-2f0ff6d4e6836ec2eb50d0a0bb26ccab88dcbac900d4eba58bb8915ee00465963</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960852410013854$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,4010,27902,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23761297$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20810278$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Ai-Tao</creatorcontrib><creatorcontrib>Yu, Hui-Lei</creatorcontrib><creatorcontrib>Pan, Jiang</creatorcontrib><creatorcontrib>Zhang, Jian-Dong</creatorcontrib><creatorcontrib>Xu, Jian-He</creatorcontrib><creatorcontrib>Lin, Guo-Qiang</creatorcontrib><title>Resolution of racemic sulfoxides with high productivity and enantioselectivity by a Rhodococcus sp. strain as an alternative to biooxidation of prochiral sulfides for efficient production of enantiopure sulfoxides</title><title>Bioresource technology</title><addtitle>Bioresour Technol</addtitle><description>Whole cells of
Rhodococcus sp. ECU0066 were used a catalyst for resolution of racemic sulfoxides, as an alternative to asymmetric oxidation of sulfides for efficient production of enantiopure sulfoxides. Racemic sulfoxides were excellent substrates for biotransformation because of their lower biotoxicity compared to sulfides. Determination of apparent kinetic parameters indicated that phenyl methyl sulfide (PMS), but not racemic phenyl methyl sulfoxide (
rac-PMSO) caused substrate inhibition. (
S)-PMSO was formed at a higher concentration and good enantiomeric excess (37.8
mM and 93.7%
ee(
S)) in a fed-batch reaction, than by an asymmetric oxidation of PMS (10
mM and 80%
ee
P (
S)). The bacterium also displayed fairly good activity (yields, 22.7–43.2%; within 1–8
h) and enantioselectivity (
ee(
S)
>
99.0%) towards
para-substituted (methyl and chloro) phenyl methyl sulfoxides and ethyl phenyl sulfoxide, indicating it could be a promising agent for synthetic applications.</description><subject>( S)-sulfoxides</subject><subject>Asymmetry</subject><subject>Biological and medical sciences</subject><subject>Bioresolution</subject><subject>Biotransformation</subject><subject>Catalysis</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrogen-Ion Concentration</subject><subject>Kinetics</subject><subject>Microbial Viability</subject><subject>Oxidation</subject><subject>Oxidation-Reduction</subject><subject>Phenyl methyl sulfide</subject><subject>Phenyls</subject><subject>Productivity</subject><subject>Racemic phenyl methyl sulfoxide</subject><subject>Rhodococcus</subject><subject>Rhodococcus - cytology</subject><subject>Rhodococcus - metabolism</subject><subject>Rhodococcus sp</subject><subject>Stereoisomerism</subject><subject>Strain</subject><subject>Substrate inhibition</subject><subject>Substrate Specificity</subject><subject>Sulfides</subject><subject>Sulfides - chemistry</subject><subject>Sulfides - metabolism</subject><subject>Sulfoxides - chemical synthesis</subject><subject>Sulfoxides - chemistry</subject><subject>Sulfoxides - metabolism</subject><subject>Temperature</subject><subject>Time Factors</subject><issn>0960-8524</issn><issn>1873-2976</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkt1u1DAQhSMEokvhFYpvENzsMnYSx7kDVfxUqoRU6LVlO-PGq2y82E6hD8r74OxPyxW9sjT-zsyx5xTFGYUVBcrfr1fa-ZDQ9CsGuQhiBax-UiyoaMolaxv-tFhAy2EpaladFC9iXANASRv2vDhhICiwRiyKP1cY_TAl50fiLQnK4MYZEqfB-t-uw0h-udST3t30ZBt8N5nkbl26I2rsCI5qzMqIAx7LOt-Qq9533nhjpkjidkViCsqNRMWsImpIGEaVeSTJk_yMeZA6OshDTO-CGnYedg6sDwStdcbhmO5d7PGDhe0U8B_TL4tnVg0RXx3O0-L686cf51-Xl9--XJx_vFyaSvC0ZBas5V2FXJQcDUNdQwcKtGbcGKWF6IxWpgXIjFa10Fq0tEYEqHjd8vK0eLvvm039nDAmuXHR4DCoEf0UpajrhjZNVT9OMlZy4EJk8t1_ydwPyrIVu6Z8j5rgYwxo5Ta4jQp3koKcYyLX8hgTOcdEgpA5Jll4dpgx6Q1297JjLjLw5gCoaNRggxqNiw9c2XCaQ5a513vOKi_VTcjM9fc8qQTasqpk8xd92BOY93DrMMg479Fg50JOjey8e8ztX-I375M</recordid><startdate>2011</startdate><enddate>2011</enddate><creator>Li, Ai-Tao</creator><creator>Yu, Hui-Lei</creator><creator>Pan, Jiang</creator><creator>Zhang, Jian-Dong</creator><creator>Xu, Jian-He</creator><creator>Lin, Guo-Qiang</creator><general>Elsevier Ltd</general><general>[New York, NY]: Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SU</scope><scope>7TB</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>KR7</scope><scope>7X8</scope><scope>7QL</scope><scope>7QO</scope><scope>7ST</scope><scope>P64</scope><scope>SOI</scope></search><sort><creationdate>2011</creationdate><title>Resolution of racemic sulfoxides with high productivity and enantioselectivity by a Rhodococcus sp. strain as an alternative to biooxidation of prochiral sulfides for efficient production of enantiopure sulfoxides</title><author>Li, Ai-Tao ; Yu, Hui-Lei ; Pan, Jiang ; Zhang, Jian-Dong ; Xu, Jian-He ; Lin, Guo-Qiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c486t-2f0ff6d4e6836ec2eb50d0a0bb26ccab88dcbac900d4eba58bb8915ee00465963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>( S)-sulfoxides</topic><topic>Asymmetry</topic><topic>Biological and medical sciences</topic><topic>Bioresolution</topic><topic>Biotransformation</topic><topic>Catalysis</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrogen-Ion Concentration</topic><topic>Kinetics</topic><topic>Microbial Viability</topic><topic>Oxidation</topic><topic>Oxidation-Reduction</topic><topic>Phenyl methyl sulfide</topic><topic>Phenyls</topic><topic>Productivity</topic><topic>Racemic phenyl methyl sulfoxide</topic><topic>Rhodococcus</topic><topic>Rhodococcus - cytology</topic><topic>Rhodococcus - metabolism</topic><topic>Rhodococcus sp</topic><topic>Stereoisomerism</topic><topic>Strain</topic><topic>Substrate inhibition</topic><topic>Substrate Specificity</topic><topic>Sulfides</topic><topic>Sulfides - chemistry</topic><topic>Sulfides - metabolism</topic><topic>Sulfoxides - chemical synthesis</topic><topic>Sulfoxides - chemistry</topic><topic>Sulfoxides - metabolism</topic><topic>Temperature</topic><topic>Time Factors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Ai-Tao</creatorcontrib><creatorcontrib>Yu, Hui-Lei</creatorcontrib><creatorcontrib>Pan, Jiang</creatorcontrib><creatorcontrib>Zhang, Jian-Dong</creatorcontrib><creatorcontrib>Xu, Jian-He</creatorcontrib><creatorcontrib>Lin, Guo-Qiang</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Environmental Engineering Abstracts</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Civil Engineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Environment Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environment Abstracts</collection><jtitle>Bioresource technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Ai-Tao</au><au>Yu, Hui-Lei</au><au>Pan, Jiang</au><au>Zhang, Jian-Dong</au><au>Xu, Jian-He</au><au>Lin, Guo-Qiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Resolution of racemic sulfoxides with high productivity and enantioselectivity by a Rhodococcus sp. strain as an alternative to biooxidation of prochiral sulfides for efficient production of enantiopure sulfoxides</atitle><jtitle>Bioresource technology</jtitle><addtitle>Bioresour Technol</addtitle><date>2011</date><risdate>2011</risdate><volume>102</volume><issue>2</issue><spage>1537</spage><epage>1542</epage><pages>1537-1542</pages><issn>0960-8524</issn><eissn>1873-2976</eissn><abstract>Whole cells of
Rhodococcus sp. ECU0066 were used a catalyst for resolution of racemic sulfoxides, as an alternative to asymmetric oxidation of sulfides for efficient production of enantiopure sulfoxides. Racemic sulfoxides were excellent substrates for biotransformation because of their lower biotoxicity compared to sulfides. Determination of apparent kinetic parameters indicated that phenyl methyl sulfide (PMS), but not racemic phenyl methyl sulfoxide (
rac-PMSO) caused substrate inhibition. (
S)-PMSO was formed at a higher concentration and good enantiomeric excess (37.8
mM and 93.7%
ee(
S)) in a fed-batch reaction, than by an asymmetric oxidation of PMS (10
mM and 80%
ee
P (
S)). The bacterium also displayed fairly good activity (yields, 22.7–43.2%; within 1–8
h) and enantioselectivity (
ee(
S)
>
99.0%) towards
para-substituted (methyl and chloro) phenyl methyl sulfoxides and ethyl phenyl sulfoxide, indicating it could be a promising agent for synthetic applications.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><pmid>20810278</pmid><doi>10.1016/j.biortech.2010.08.025</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-8524 |
| ispartof | Bioresource technology, 2011, Vol.102 (2), p.1537-1542 |
| issn | 0960-8524 1873-2976 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_855717745 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | ( S)-sulfoxides Asymmetry Biological and medical sciences Bioresolution Biotransformation Catalysis Fundamental and applied biological sciences. Psychology Hydrogen-Ion Concentration Kinetics Microbial Viability Oxidation Oxidation-Reduction Phenyl methyl sulfide Phenyls Productivity Racemic phenyl methyl sulfoxide Rhodococcus Rhodococcus - cytology Rhodococcus - metabolism Rhodococcus sp Stereoisomerism Strain Substrate inhibition Substrate Specificity Sulfides Sulfides - chemistry Sulfides - metabolism Sulfoxides - chemical synthesis Sulfoxides - chemistry Sulfoxides - metabolism Temperature Time Factors |
| title | Resolution of racemic sulfoxides with high productivity and enantioselectivity by a Rhodococcus sp. strain as an alternative to biooxidation of prochiral sulfides for efficient production of enantiopure sulfoxides |
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