Chemoenzymatic total synthesis of rotigotine IRED-catalyzed reductive amination
A short and chemoenzymatic synthesis of rotigotine using an IR-36-M5 mutant is reported. Focusing on the residues that directly contact the 2-tetralone moiety, we applied structure-guided semi-rational design to obtain a double-mutant F260W/M147Y, which showed a good isolated yield and S -stereosele...
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2024-05, Vol.22 (19), p.3843-3847 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3847 |
|---|---|
| container_issue | 19 |
| container_start_page | 3843 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 22 |
| creator | Tang, Dongyu Ma, Yaqing Bao, Jinping Gao, Shushan Man, Shuli Cui, Chengsen |
| description | A short and chemoenzymatic synthesis of rotigotine using an IR-36-M5 mutant is reported. Focusing on the residues that directly contact the 2-tetralone moiety, we applied structure-guided semi-rational design to obtain a double-mutant F260W/M147Y, which showed a good isolated yield and
S
-stereoselectivity >99% toward 2-aminotetralin synthesis. Furthermore, the utility of this biocatalytic protocol was successfully demonstrated in the enantioselective synthesis of rotigotine
via
enzymatic reductive amination as the key step.
An engineered imine reductase (IRED) was developed specifically for 2-tetralone substrate, and utilized in the total synthesis of rotigotine. |
| doi_str_mv | 10.1039/d4ob00072b |
| format | Article |
| fullrecord | <record><control><sourceid>rsc</sourceid><recordid>TN_cdi_rsc_primary_d4ob00072b</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>d4ob00072b</sourcerecordid><originalsourceid>FETCH-rsc_primary_d4ob00072b3</originalsourceid><addsrcrecordid>eNqFjj0LwjAYhIMoWD8WdyF_oPqmrYbOVdFJEPeSpqmNNIkkUWh_vR1ER4fjDp47OIQWBFYE4nRdJqYAABoVAxSQhNIQNnE6_OYIxmji3B2ApHSbBOic1UIZobtWMS859sazBrtW-1o46bCpsDVe3nppgU-X_S7krK-0nSixFeWTe_kSmCmp-73RMzSqWOPE_ONTtDzsr9kxtI7nDysVs23-exn_428rcUFU</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Chemoenzymatic total synthesis of rotigotine IRED-catalyzed reductive amination</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Tang, Dongyu ; Ma, Yaqing ; Bao, Jinping ; Gao, Shushan ; Man, Shuli ; Cui, Chengsen</creator><creatorcontrib>Tang, Dongyu ; Ma, Yaqing ; Bao, Jinping ; Gao, Shushan ; Man, Shuli ; Cui, Chengsen</creatorcontrib><description>A short and chemoenzymatic synthesis of rotigotine using an IR-36-M5 mutant is reported. Focusing on the residues that directly contact the 2-tetralone moiety, we applied structure-guided semi-rational design to obtain a double-mutant F260W/M147Y, which showed a good isolated yield and
S
-stereoselectivity >99% toward 2-aminotetralin synthesis. Furthermore, the utility of this biocatalytic protocol was successfully demonstrated in the enantioselective synthesis of rotigotine
via
enzymatic reductive amination as the key step.
An engineered imine reductase (IRED) was developed specifically for 2-tetralone substrate, and utilized in the total synthesis of rotigotine.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d4ob00072b</identifier><ispartof>Organic & biomolecular chemistry, 2024-05, Vol.22 (19), p.3843-3847</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Tang, Dongyu</creatorcontrib><creatorcontrib>Ma, Yaqing</creatorcontrib><creatorcontrib>Bao, Jinping</creatorcontrib><creatorcontrib>Gao, Shushan</creatorcontrib><creatorcontrib>Man, Shuli</creatorcontrib><creatorcontrib>Cui, Chengsen</creatorcontrib><title>Chemoenzymatic total synthesis of rotigotine IRED-catalyzed reductive amination</title><title>Organic & biomolecular chemistry</title><description>A short and chemoenzymatic synthesis of rotigotine using an IR-36-M5 mutant is reported. Focusing on the residues that directly contact the 2-tetralone moiety, we applied structure-guided semi-rational design to obtain a double-mutant F260W/M147Y, which showed a good isolated yield and
S
-stereoselectivity >99% toward 2-aminotetralin synthesis. Furthermore, the utility of this biocatalytic protocol was successfully demonstrated in the enantioselective synthesis of rotigotine
via
enzymatic reductive amination as the key step.
An engineered imine reductase (IRED) was developed specifically for 2-tetralone substrate, and utilized in the total synthesis of rotigotine.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFjj0LwjAYhIMoWD8WdyF_oPqmrYbOVdFJEPeSpqmNNIkkUWh_vR1ER4fjDp47OIQWBFYE4nRdJqYAABoVAxSQhNIQNnE6_OYIxmji3B2ApHSbBOic1UIZobtWMS859sazBrtW-1o46bCpsDVe3nppgU-X_S7krK-0nSixFeWTe_kSmCmp-73RMzSqWOPE_ONTtDzsr9kxtI7nDysVs23-exn_428rcUFU</recordid><startdate>20240515</startdate><enddate>20240515</enddate><creator>Tang, Dongyu</creator><creator>Ma, Yaqing</creator><creator>Bao, Jinping</creator><creator>Gao, Shushan</creator><creator>Man, Shuli</creator><creator>Cui, Chengsen</creator><scope/></search><sort><creationdate>20240515</creationdate><title>Chemoenzymatic total synthesis of rotigotine IRED-catalyzed reductive amination</title><author>Tang, Dongyu ; Ma, Yaqing ; Bao, Jinping ; Gao, Shushan ; Man, Shuli ; Cui, Chengsen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_d4ob00072b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tang, Dongyu</creatorcontrib><creatorcontrib>Ma, Yaqing</creatorcontrib><creatorcontrib>Bao, Jinping</creatorcontrib><creatorcontrib>Gao, Shushan</creatorcontrib><creatorcontrib>Man, Shuli</creatorcontrib><creatorcontrib>Cui, Chengsen</creatorcontrib><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tang, Dongyu</au><au>Ma, Yaqing</au><au>Bao, Jinping</au><au>Gao, Shushan</au><au>Man, Shuli</au><au>Cui, Chengsen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemoenzymatic total synthesis of rotigotine IRED-catalyzed reductive amination</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2024-05-15</date><risdate>2024</risdate><volume>22</volume><issue>19</issue><spage>3843</spage><epage>3847</epage><pages>3843-3847</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A short and chemoenzymatic synthesis of rotigotine using an IR-36-M5 mutant is reported. Focusing on the residues that directly contact the 2-tetralone moiety, we applied structure-guided semi-rational design to obtain a double-mutant F260W/M147Y, which showed a good isolated yield and
S
-stereoselectivity >99% toward 2-aminotetralin synthesis. Furthermore, the utility of this biocatalytic protocol was successfully demonstrated in the enantioselective synthesis of rotigotine
via
enzymatic reductive amination as the key step.
An engineered imine reductase (IRED) was developed specifically for 2-tetralone substrate, and utilized in the total synthesis of rotigotine.</abstract><doi>10.1039/d4ob00072b</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2024-05, Vol.22 (19), p.3843-3847 |
| issn | 1477-0520 1477-0539 |
| language | |
| recordid | cdi_rsc_primary_d4ob00072b |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Chemoenzymatic total synthesis of rotigotine IRED-catalyzed reductive amination |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T21%3A17%3A31IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-rsc&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Chemoenzymatic%20total%20synthesis%20of%20rotigotine%20IRED-catalyzed%20reductive%20amination&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Tang,%20Dongyu&rft.date=2024-05-15&rft.volume=22&rft.issue=19&rft.spage=3843&rft.epage=3847&rft.pages=3843-3847&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/d4ob00072b&rft_dat=%3Crsc%3Ed4ob00072b%3C/rsc%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |