Chemoenzymatic total synthesis of rotigotine via 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 -stereoselect...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2024-05, Vol.22 (19), p.3843-3847
Hauptverfasser: Tang, Dongyu, Ma, Yaqing, Bao, Jinping, Gao, Shushan, Man, Shuli, Cui, Chengsen
Format: Artikel
Sprache:eng
Schlagworte:
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 -stereoselectivity >99% toward 2-aminotetralin synthesis. Furthermore, the utility of this biocatalytic protocol was successfully demonstrated in the enantioselective synthesis of rotigotine enzymatic reductive amination as the key step.
doi_str_mv 10.1039/d4ob00072b
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3039236266</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3039236266</sourcerecordid><originalsourceid>FETCH-LOGICAL-c274t-fefd34ff9c4c097541d423e106ceac1ae3e85dc0cd40bc0a277a76ae1dee6e013</originalsourceid><addsrcrecordid>eNpd0MtKw0AUBuBBFFurGx9AAm5EiM4tmWZpL2qhUPCyDpOZE5uSZGpmUkif3qmtXbg4nLP4-Dn8CF0T_EAwSx41NxnGWNDsBPUJFyLEEUtOjzfFPXRh7QpjkoiYn6MeG8ZkmHDaR-_jJVQG6m1XSVeowBkny8B2tVuCLWxg8qAxrvjyU0OwKWQwe5tOQiU967aggwZ0q1yxgUBWRe0zTH2JznJZWrg67AH6fJ5-jF_D-eJlNn6ah4oK7sIccs14nieKK5yIiBPNKQOCYwVSEQkMhpFWWGmOM4UlFUKKWALRADFgwgbobp-7bsx3C9alVWEVlKWswbQ2Zb4cymIax57e_qMr0za1_86riIskiYY7db9XqjHWNpCn66aoZNOlBKe7qtMJX4x-qx55fHOIbLMK9JH-dct-AHNIekw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3054799586</pqid></control><display><type>article</type><title>Chemoenzymatic total synthesis of rotigotine via 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 -stereoselectivity &gt;99% toward 2-aminotetralin synthesis. Furthermore, the utility of this biocatalytic protocol was successfully demonstrated in the enantioselective synthesis of rotigotine enzymatic reductive amination as the key step.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d4ob00072b</identifier><identifier>PMID: 38618942</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Amination ; Chemical synthesis ; Enantiomers ; Mutants ; Stereoselectivity</subject><ispartof>Organic &amp; biomolecular chemistry, 2024-05, Vol.22 (19), p.3843-3847</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c274t-fefd34ff9c4c097541d423e106ceac1ae3e85dc0cd40bc0a277a76ae1dee6e013</cites><orcidid>0000-0002-6867-1826</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38618942$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></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 via IRED-catalyzed reductive amination</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><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 -stereoselectivity &gt;99% toward 2-aminotetralin synthesis. Furthermore, the utility of this biocatalytic protocol was successfully demonstrated in the enantioselective synthesis of rotigotine enzymatic reductive amination as the key step.</description><subject>Amination</subject><subject>Chemical synthesis</subject><subject>Enantiomers</subject><subject>Mutants</subject><subject>Stereoselectivity</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpd0MtKw0AUBuBBFFurGx9AAm5EiM4tmWZpL2qhUPCyDpOZE5uSZGpmUkif3qmtXbg4nLP4-Dn8CF0T_EAwSx41NxnGWNDsBPUJFyLEEUtOjzfFPXRh7QpjkoiYn6MeG8ZkmHDaR-_jJVQG6m1XSVeowBkny8B2tVuCLWxg8qAxrvjyU0OwKWQwe5tOQiU967aggwZ0q1yxgUBWRe0zTH2JznJZWrg67AH6fJ5-jF_D-eJlNn6ah4oK7sIccs14nieKK5yIiBPNKQOCYwVSEQkMhpFWWGmOM4UlFUKKWALRADFgwgbobp-7bsx3C9alVWEVlKWswbQ2Zb4cymIax57e_qMr0za1_86riIskiYY7db9XqjHWNpCn66aoZNOlBKe7qtMJX4x-qx55fHOIbLMK9JH-dct-AHNIekw</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><general>Royal Society of Chemistry</general><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/0000-0002-6867-1826</orcidid></search><sort><creationdate>20240515</creationdate><title>Chemoenzymatic total synthesis of rotigotine via 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-LOGICAL-c274t-fefd34ff9c4c097541d423e106ceac1ae3e85dc0cd40bc0a277a76ae1dee6e013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Amination</topic><topic>Chemical synthesis</topic><topic>Enantiomers</topic><topic>Mutants</topic><topic>Stereoselectivity</topic><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><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 &amp; 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 via IRED-catalyzed reductive amination</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><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 -stereoselectivity &gt;99% toward 2-aminotetralin synthesis. Furthermore, the utility of this biocatalytic protocol was successfully demonstrated in the enantioselective synthesis of rotigotine enzymatic reductive amination as the key step.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38618942</pmid><doi>10.1039/d4ob00072b</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-6867-1826</orcidid></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 eng
recordid cdi_proquest_miscellaneous_3039236266
source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Amination
Chemical synthesis
Enantiomers
Mutants
Stereoselectivity
title Chemoenzymatic total synthesis of rotigotine via 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%3A41%3A21IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Chemoenzymatic%20total%20synthesis%20of%20rotigotine%20via%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=%3Cproquest_cross%3E3039236266%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3054799586&rft_id=info:pmid/38618942&rfr_iscdi=true