Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B
Optically pure sulfoxides are noteworthy compounds that find wide applications in various industrial fields. Here, we report a methionine sulfoxide reductase B (MsrB) homologue that exhibits high enantioselectivity and broad substrate scope for the kinetic resolution of racemic ( rac ) sulfoxides. T...
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Veröffentlicht in: | Organic & biomolecular chemistry 2023-04, Vol.21 (16), p.3417-3422 |
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container_title | Organic & biomolecular chemistry |
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creator | Zhao, Yuyan Jiang, Xu Zhou, Shihuan Tian, Jin Yang, Piao Chen, Yanli Zhang, Quan Xu, Xianlin Chen, Yongzheng Yang, Jiawei |
description | Optically pure sulfoxides are noteworthy compounds that find wide applications in various industrial fields. Here, we report a methionine sulfoxide reductase B (MsrB) homologue that exhibits high enantioselectivity and broad substrate scope for the kinetic resolution of racemic (
rac
) sulfoxides. This MsrB homologue, named
li
MsrB, was identified from
Limnohabitans
sp. 103DPR2 and showed good activity together with enantioselectivity towards a series of aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides. Chiral sulfoxides in the
S
configuration were prepared in approximately 50% yield and 92-99% enantiomeric excess through kinetic resolution at an initial substrate concentration of up to 90 mM (11.2 g L
−1
). This study presents an efficient route for the enzymatic preparation of (
S
)-sulfoxides through kinetic resolution.
A range of sulfoxides including aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides in the
S
configuration were prepared through kinetic resolution catalyzed by a new MsrB enzyme. |
doi_str_mv | 10.1039/d3ob00402c |
format | Article |
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rac
) sulfoxides. This MsrB homologue, named
li
MsrB, was identified from
Limnohabitans
sp. 103DPR2 and showed good activity together with enantioselectivity towards a series of aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides. Chiral sulfoxides in the
S
configuration were prepared in approximately 50% yield and 92-99% enantiomeric excess through kinetic resolution at an initial substrate concentration of up to 90 mM (11.2 g L
−1
). This study presents an efficient route for the enzymatic preparation of (
S
)-sulfoxides through kinetic resolution.
A range of sulfoxides including aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides in the
S
configuration were prepared through kinetic resolution catalyzed by a new MsrB enzyme.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d3ob00402c</identifier><identifier>PMID: 37017279</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Enantiomers ; Homology ; Kinetics ; Methionine ; Methionine Sulfoxide Reductases ; Reductases ; Stereoisomerism ; Substrates ; Sulfoxides ; Sulfoxides - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2023-04, Vol.21 (16), p.3417-3422</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-dd86e84149b741de82a9c1c0cf38886ee4a673c18d56829399d123ad859695243</citedby><cites>FETCH-LOGICAL-c337t-dd86e84149b741de82a9c1c0cf38886ee4a673c18d56829399d123ad859695243</cites><orcidid>0000-0003-1211-3486 ; 0000-0001-6632-2238</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27907,27908</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37017279$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhao, Yuyan</creatorcontrib><creatorcontrib>Jiang, Xu</creatorcontrib><creatorcontrib>Zhou, Shihuan</creatorcontrib><creatorcontrib>Tian, Jin</creatorcontrib><creatorcontrib>Yang, Piao</creatorcontrib><creatorcontrib>Chen, Yanli</creatorcontrib><creatorcontrib>Zhang, Quan</creatorcontrib><creatorcontrib>Xu, Xianlin</creatorcontrib><creatorcontrib>Chen, Yongzheng</creatorcontrib><creatorcontrib>Yang, Jiawei</creatorcontrib><title>Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Optically pure sulfoxides are noteworthy compounds that find wide applications in various industrial fields. Here, we report a methionine sulfoxide reductase B (MsrB) homologue that exhibits high enantioselectivity and broad substrate scope for the kinetic resolution of racemic (
rac
) sulfoxides. This MsrB homologue, named
li
MsrB, was identified from
Limnohabitans
sp. 103DPR2 and showed good activity together with enantioselectivity towards a series of aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides. Chiral sulfoxides in the
S
configuration were prepared in approximately 50% yield and 92-99% enantiomeric excess through kinetic resolution at an initial substrate concentration of up to 90 mM (11.2 g L
−1
). This study presents an efficient route for the enzymatic preparation of (
S
)-sulfoxides through kinetic resolution.
A range of sulfoxides including aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides in the
S
configuration were prepared through kinetic resolution catalyzed by a new MsrB enzyme.</description><subject>Enantiomers</subject><subject>Homology</subject><subject>Kinetics</subject><subject>Methionine</subject><subject>Methionine Sulfoxide Reductases</subject><subject>Reductases</subject><subject>Stereoisomerism</subject><subject>Substrates</subject><subject>Sulfoxides</subject><subject>Sulfoxides - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkU1P3DAQhq0KVD7aC3cqS1xQpS3-SmwfYaEtKtJe2nPktScboySmsc3Cv69ht4vEaUaaR8-M5kXohJJvlHB94XhYEiIIsx_QIRVSzkjF9d6uZ-QAHcV4TwjVshYf0QGXhEom9SFa__IjJG_xBDH0Ofkw4tDimPs2PHkHEa996nDnVx2G0YwFiNCDTf7Rp2ecox9X2OAR1rgLQ-jDKsOLYIDUFVeRv7nKDpdtMhHw1Se035o-wudtPUZ_vt_8nv-c3S1-3M4v72aWc5lmzqkalKBCL6WgDhQz2lJLbMuVKiMQppbcUuWqWjHNtXaUceNUpWtdMcGP0fnG-zCFvxliagYfLfS9GSHk2JQn1LRmktYFPXuH3oc8jeW6hilSqaoSjBTq64ayU4hxgrZ5mPxgpueGkuYljuaaL65e45gX-MtWmZcDuB36__8FON0AU7S76Vue_B8P6Y_j</recordid><startdate>20230426</startdate><enddate>20230426</enddate><creator>Zhao, Yuyan</creator><creator>Jiang, Xu</creator><creator>Zhou, Shihuan</creator><creator>Tian, Jin</creator><creator>Yang, Piao</creator><creator>Chen, Yanli</creator><creator>Zhang, Quan</creator><creator>Xu, Xianlin</creator><creator>Chen, Yongzheng</creator><creator>Yang, Jiawei</creator><general>Royal Society of Chemistry</general><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>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1211-3486</orcidid><orcidid>https://orcid.org/0000-0001-6632-2238</orcidid></search><sort><creationdate>20230426</creationdate><title>Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B</title><author>Zhao, Yuyan ; Jiang, Xu ; Zhou, Shihuan ; Tian, Jin ; Yang, Piao ; Chen, Yanli ; Zhang, Quan ; Xu, Xianlin ; Chen, Yongzheng ; Yang, Jiawei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-dd86e84149b741de82a9c1c0cf38886ee4a673c18d56829399d123ad859695243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Enantiomers</topic><topic>Homology</topic><topic>Kinetics</topic><topic>Methionine</topic><topic>Methionine Sulfoxide Reductases</topic><topic>Reductases</topic><topic>Stereoisomerism</topic><topic>Substrates</topic><topic>Sulfoxides</topic><topic>Sulfoxides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhao, Yuyan</creatorcontrib><creatorcontrib>Jiang, Xu</creatorcontrib><creatorcontrib>Zhou, Shihuan</creatorcontrib><creatorcontrib>Tian, Jin</creatorcontrib><creatorcontrib>Yang, Piao</creatorcontrib><creatorcontrib>Chen, Yanli</creatorcontrib><creatorcontrib>Zhang, Quan</creatorcontrib><creatorcontrib>Xu, Xianlin</creatorcontrib><creatorcontrib>Chen, Yongzheng</creatorcontrib><creatorcontrib>Yang, Jiawei</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhao, Yuyan</au><au>Jiang, Xu</au><au>Zhou, Shihuan</au><au>Tian, Jin</au><au>Yang, Piao</au><au>Chen, Yanli</au><au>Zhang, Quan</au><au>Xu, Xianlin</au><au>Chen, Yongzheng</au><au>Yang, Jiawei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2023-04-26</date><risdate>2023</risdate><volume>21</volume><issue>16</issue><spage>3417</spage><epage>3422</epage><pages>3417-3422</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Optically pure sulfoxides are noteworthy compounds that find wide applications in various industrial fields. Here, we report a methionine sulfoxide reductase B (MsrB) homologue that exhibits high enantioselectivity and broad substrate scope for the kinetic resolution of racemic (
rac
) sulfoxides. This MsrB homologue, named
li
MsrB, was identified from
Limnohabitans
sp. 103DPR2 and showed good activity together with enantioselectivity towards a series of aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides. Chiral sulfoxides in the
S
configuration were prepared in approximately 50% yield and 92-99% enantiomeric excess through kinetic resolution at an initial substrate concentration of up to 90 mM (11.2 g L
−1
). This study presents an efficient route for the enzymatic preparation of (
S
)-sulfoxides through kinetic resolution.
A range of sulfoxides including aromatic, heteroaromatic, alkyl and thioalkyl sulfoxides in the
S
configuration were prepared through kinetic resolution catalyzed by a new MsrB enzyme.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37017279</pmid><doi>10.1039/d3ob00402c</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-1211-3486</orcidid><orcidid>https://orcid.org/0000-0001-6632-2238</orcidid></addata></record> |
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source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Enantiomers Homology Kinetics Methionine Methionine Sulfoxide Reductases Reductases Stereoisomerism Substrates Sulfoxides Sulfoxides - chemistry |
title | Kinetic resolution of sulfoxides with high enantioselectivity using a new homologue of methionine sulfoxide reductase B |
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